MiMeDB: Showing metabocard for 5,10-Methenyltetrahydrofolic acid (MMDBc0031998)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:58:02 UTC

Update Date

2022-08-31 18:27:26 UTC

MiMeDB ID

MMDBc0031998

Metabolite Identification

Common Name

5,10-Methenyltetrahydrofolic acid

Description

NULL

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

644350
  Mrv1652309042000212D          

 34 37  0  0  1  0            999 V2000
    1.9058    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    1.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -2.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1626    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -1.6629    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.2059   -0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0831    1.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806    0.1786    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.9184   -0.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096   -0.6464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3603    0.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6227    1.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -0.9484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9683   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806   -0.6464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3999   -0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951   -1.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3999    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3669    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096    0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818    1.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951    0.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0934   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1108   -1.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  2  0  0  0  0
  3 21  2  0  0  0  0
  4 22  2  0  0  0  0
  5 26  2  0  0  0  0
  6 21  1  0  0  0  0
 14  7  1  6  0  0  0
  7 22  1  0  0  0  0
  8 24  1  0  0  0  0
  9 17  1  0  0  0  0
  9 23  2  0  0  0  0
  9 27  1  0  0  0  0
 10 18  1  0  0  0  0
 10 23  1  0  0  0  0
 10 28  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 13 24  2  0  0  0  0
 13 26  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 34  1  1  0  0  0
 22 29  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 32  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  CHG  2   6  -1   9   1
M  END

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

644350
  Mrv1652309042000212D          

 34 37  0  0  1  0            999 V2000
    1.9058    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433    1.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -2.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2059    0.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1626    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -1.6629    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.2059   -0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0831    1.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806    0.1786    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.9184   -0.2339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096   -0.6464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3603    0.5967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6227    1.8857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3808   -0.9484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9683   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1806   -0.6464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3999   -0.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951   -1.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7308    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9683   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3999    0.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3669    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096    0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8818    1.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8951    0.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0934   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -0.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6809   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559    0.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8559   -0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1108   -1.3027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 20  2  0  0  0  0
  3 21  2  0  0  0  0
  4 22  2  0  0  0  0
  5 26  2  0  0  0  0
  6 21  1  0  0  0  0
 14  7  1  6  0  0  0
  7 22  1  0  0  0  0
  8 24  1  0  0  0  0
  9 17  1  0  0  0  0
  9 23  2  0  0  0  0
  9 27  1  0  0  0  0
 10 18  1  0  0  0  0
 10 23  1  0  0  0  0
 10 28  1  0  0  0  0
 11 19  1  0  0  0  0
 11 25  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 13 24  2  0  0  0  0
 13 26  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 34  1  1  0  0  0
 22 29  1  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
 28 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 32  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  CHG  2   6  -1   9   1
M  END
> <DATABASE_ID>
MMDBc0031998

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1

> <INCHI_KEY>
MEANFMOQMXYMCT-OLZOCXBDSA-N

> <FORMULA>
C20H21N7O6

> <MOLECULAR_WEIGHT>
455.424

> <EXACT_MASS>
455.155331439

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.38318064408257

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-3.2723940359857626

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.7122602199699957

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.985128746522236

> <JCHEM_PKA_STRONGEST_BASIC>
2.0370736672090084

> <JCHEM_POLAR_SURFACE_AREA>
196.76999999999998

> <JCHEM_REFRACTIVITY>
155.82450000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 644350                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       3.557   0.897   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.867   2.231   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.177  -4.438   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.718   0.897   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      18.970   3.462   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.867  -3.104   0.000  0.00  0.00           O-1
HETATM    7  N   UNK     0       9.718  -1.770   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      24.422   3.483   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      19.004   0.333   0.000  0.00  0.00           N+1
HETATM   10  N   UNK     0      16.648  -0.437   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      21.671  -1.207   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      23.073   1.114   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      21.696   3.520   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.177  -1.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.407  -0.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.867  -0.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.004  -1.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.546  -1.676   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.338  -1.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.097   0.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.407  -3.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.488  -0.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.546   0.803   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.085   2.718   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      21.671   0.333   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.313   2.707   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.338   1.103   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.108  -0.437   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.028  -0.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.338   0.897   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.338  -1.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.798   0.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.798  -1.770   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      18.873  -2.432   0.000  0.00  0.00           H+0
CONECT    1   20                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   26                                                            
CONECT    6   21                                                            
CONECT    7   14   22                                                       
CONECT    8   24                                                            
CONECT    9   17   23   27                                                  
CONECT   10   18   23   28                                                  
CONECT   11   19   25                                                       
CONECT   12   24   25                                                       
CONECT   13   24   26                                                       
CONECT   14    7   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17    9   18   19   34                                             
CONECT   18   10   17                                                       
CONECT   19   11   17                                                       
CONECT   20    1    2   16                                                  
CONECT   21    3    6   14                                                  
CONECT   22    4    7   29                                                  
CONECT   23    9   10                                                       
CONECT   24    8   12   13                                                  
CONECT   25   11   12   27                                                  
CONECT   26    5   13   27                                                  
CONECT   27    9   25   26                                                  
CONECT   28   10   30   31                                                  
CONECT   29   22   32   33                                                  
CONECT   30   28   32                                                       
CONECT   31   28   33                                                       
CONECT   32   29   30                                                       
CONECT   33   29   31                                                       
CONECT   34   17                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0001354
HETATM    1  N1  UNL     1      -8.864   1.735  -1.732  1.00  0.00           N  
HETATM    2  C1  UNL     1      -7.552   1.375  -1.267  1.00  0.00           C  
HETATM    3  N2  UNL     1      -6.466   1.532  -2.037  1.00  0.00           N  
HETATM    4  C2  UNL     1      -5.208   1.207  -1.642  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.212   1.362  -2.375  1.00  0.00           O  
HETATM    6  C3  UNL     1      -5.043   0.692  -0.392  1.00  0.00           C  
HETATM    7  C4  UNL     1      -6.150   0.525   0.412  1.00  0.00           C  
HETATM    8  N3  UNL     1      -7.396   0.868  -0.034  1.00  0.00           N  
HETATM    9  N4  UNL     1      -5.960  -0.010   1.707  1.00  0.00           N  
HETATM   10  C5  UNL     1      -4.701  -0.474   2.238  1.00  0.00           C  
HETATM   11  C6  UNL     1      -3.644  -0.629   1.184  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.302  -0.305   1.791  1.00  0.00           C  
HETATM   13  N5  UNL     1      -1.586   0.073   0.558  1.00  0.00           N  
HETATM   14  C8  UNL     1      -0.229  -0.169   0.294  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.618  -0.773   1.197  1.00  0.00           C  
HETATM   16  C10 UNL     1       1.949  -1.005   0.925  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.499  -0.638  -0.277  1.00  0.00           C  
HETATM   18  C12 UNL     1       3.890  -0.835  -0.655  1.00  0.00           C  
HETATM   19  O2  UNL     1       4.260  -0.661  -1.849  1.00  0.00           O  
HETATM   20  N6  UNL     1       4.819  -1.223   0.331  1.00  0.00           N  
HETATM   21  C13 UNL     1       6.217  -1.414  -0.093  1.00  0.00           C  
HETATM   22  C14 UNL     1       7.023  -0.486   0.785  1.00  0.00           C  
HETATM   23  C15 UNL     1       6.565   0.924   0.570  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.756   1.407  -0.813  1.00  0.00           C  
HETATM   25  O3  UNL     1       7.307   0.714  -1.697  1.00  0.00           O  
HETATM   26  O4  UNL     1       6.318   2.688  -1.191  1.00  0.00           O  
HETATM   27  C17 UNL     1       6.605  -2.844   0.171  1.00  0.00           C  
HETATM   28  O5  UNL     1       7.357  -3.143   1.122  1.00  0.00           O  
HETATM   29  O6  UNL     1       6.111  -3.822  -0.663  1.00  0.00           O1-
HETATM   30  C18 UNL     1       1.660  -0.023  -1.209  1.00  0.00           C  
HETATM   31  C19 UNL     1       0.335   0.196  -0.912  1.00  0.00           C  
HETATM   32  C20 UNL     1      -2.583   0.711  -0.236  1.00  0.00           C  
HETATM   33  N7  UNL     1      -3.754   0.319   0.122  1.00  0.00           N1+
HETATM   34  H1  UNL     1      -9.421   2.504  -1.350  1.00  0.00           H  
HETATM   35  H2  UNL     1      -9.268   1.171  -2.510  1.00  0.00           H  
HETATM   36  H3  UNL     1      -8.217   0.735   0.585  1.00  0.00           H  
HETATM   37  H4  UNL     1      -6.793  -0.079   2.338  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.404   0.222   3.050  1.00  0.00           H  
HETATM   39  H6  UNL     1      -4.854  -1.480   2.704  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.581  -1.651   0.760  1.00  0.00           H  
HETATM   41  H8  UNL     1      -2.422   0.586   2.457  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.836  -1.153   2.295  1.00  0.00           H  
HETATM   43  H10 UNL     1       0.193  -1.071   2.159  1.00  0.00           H  
HETATM   44  H11 UNL     1       2.576  -1.482   1.656  1.00  0.00           H  
HETATM   45  H12 UNL     1       4.539  -1.368   1.311  1.00  0.00           H  
HETATM   46  H13 UNL     1       6.318  -1.249  -1.161  1.00  0.00           H  
HETATM   47  H14 UNL     1       6.806  -0.737   1.846  1.00  0.00           H  
HETATM   48  H15 UNL     1       8.110  -0.557   0.569  1.00  0.00           H  
HETATM   49  H16 UNL     1       5.465   1.002   0.817  1.00  0.00           H  
HETATM   50  H17 UNL     1       7.141   1.608   1.259  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.526   2.754  -1.818  1.00  0.00           H  
HETATM   52  H19 UNL     1       2.092   0.275  -2.176  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.300   0.677  -1.654  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.310   1.421  -1.020  1.00  0.00           H  
CONECT    1    2   34   35
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   33
CONECT    7    8    9
CONECT    8   36
CONECT    9   10   37
CONECT   10   11   38   39
CONECT   11   12   33   40
CONECT   12   13   41   42
CONECT   13   14   32
CONECT   14   15   15   31
CONECT   15   16   43
CONECT   16   17   17   44
CONECT   17   18   30
CONECT   18   19   19   20
CONECT   20   21   45
CONECT   21   22   27   46
CONECT   22   23   47   48
CONECT   23   24   49   50
CONECT   24   25   25   26
CONECT   26   51
CONECT   27   28   28   29
CONECT   30   31   31   52
CONECT   31   53
CONECT   32   33   33   54
END

HMDB0001354
     RDKit          3D
5,10-Methenyltetrahydrofolic acid
 54 57  0  0  0  0  0  0  0  0999 V2000
   -8.8642    1.7349   -1.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5520    1.3753   -1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4659    1.5324   -2.0374 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2076    1.2072   -1.6419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2123    1.3619   -2.3754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0426    0.6924   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1500    0.5250    0.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3956    0.8683   -0.0338 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -0.0100    1.7067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7011   -0.4744    2.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6437   -0.6293    1.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3018   -0.3055    1.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.0731    0.5578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288   -0.1688    0.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -0.7731    1.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9494   -1.0054    0.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -0.6380   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8903   -0.8352   -0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.6610   -1.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8193   -1.2232    0.3313 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2175   -1.4141   -0.0935 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0231   -0.4861    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5647    0.9236    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7564    1.4067   -0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070    0.7139   -1.6968 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3175    2.6877   -1.1911 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055   -2.8440    0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3572   -3.1432    1.1225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110   -3.8223   -0.6630 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6597   -0.0234   -1.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3351    0.1961   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5833    0.7110   -0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541    0.3191    0.1216 N   0  0  0  0  0  4  0  0  0  0  0  0
   -9.4205    2.5045   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2683    1.1707   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2175    0.7352    0.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -0.0785    2.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044    0.2215    3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8544   -1.4799    2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -1.6513    0.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4217    0.5863    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8356   -1.1534    2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   -1.0714    2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5763   -1.4818    1.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392   -1.3677    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3182   -1.2493   -1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8056   -0.7366    1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1103   -0.5572    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646    1.0017    0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1412    1.6077    1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262    2.7540   -1.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921    0.2754   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3003    0.6770   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103    1.4212   -1.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 21 27  1  0
 27 28  2  0
 27 29  1  0
 17 30  1  0
 30 31  2  0
 13 32  1  0
 32 33  2  0
  8  2  1  0
 33 11  1  0
 33  6  1  0
 31 14  1  0
  1 34  1  0
  1 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 15 43  1  0
 16 44  1  0
 20 45  1  0
 21 46  1  6
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 26 51  1  0
 30 52  1  0
 31 53  1  0
 32 54  1  0
M  CHG  2  29  -1  33   1
M  END

Synonyms

Value	Source
5,10-Methenyltetrahydrofolate	Generator
5,10-Methenyl-THF	HMDB
Anhydro-leucovorin	HMDB
Anhydro-leucovorin a	HMDB
Anhydroleucovorin	HMDB
Anhydroleucovorin a	HMDB
CH-THF	HMDB
Methenyl-tetrahydrofolate	HMDB
Methenyl-THF	HMDB
Methenyltetrahydrofolate	HMDB
Methenyltetrahydrofolic acid	HMDB
N5-N10-CH-THF	HMDB
N5-N10-Methenyltetrahydrofolate	HMDB
5,10-Methenyltetrahydropteroylglutamate	HMDB
N5,N10-Methenyl tetrahydrofolate	HMDB

Chemical Formula

C₂₀H₂₁N₇O₆

Average Molecular Weight

455.424

Monoisotopic Molecular Weight

455.155331439

IUPAC Name

(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-3H,4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

Traditional Name

(6aR)-8-(4-{[(1S)-1,3-dicarboxypropyl]-C-hydroxycarbonimidoyl}phenyl)-1-hydroxy-3-imino-4H,5H,6H,6aH,7H-8lambda5-imidazo[1,5-f]pteridin-8-ylium

CAS Registry Number

Not Available

SMILES

[H][C@@]12CN(C=[N+]1C1=C(NC2)NC(N)=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C([O-])=O

InChI Identifier

InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,9,12-13H,5-8H2,(H6-,21,22,23,24,25,28,29,30,31,32,33)/t12-,13+/m1/s1

InChI Key

MEANFMOQMXYMCT-OLZOCXBDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofolic acids. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic acids

Alternative Parents

Substituents

Tetrahydrofolic acid
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Alpha-amino acid or derivatives
Benzamide
Benzoic acid or derivatives
Aniline or substituted anilines
Benzoyl
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Pyrimidine
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous amide
Heteroaromatic compound
2-imidazoline
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid salt
Amino acid or derivatives
Amidine
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid
Secondary amine
Organic oxygen compound
Amine
Carbonyl group
Organic salt
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organic zwitterion
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	-0.68	ALOGPS
logP	-3.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	2.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	196.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	155.82 m³·mol⁻¹	ChemAxon
Polarizability	45.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2408900000-90c26f197ed01948843b	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0230-9506630000-d9b025a3f36832b17d97	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-9a74d30be444557240b0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000900000-87ffec278a0d552070d3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9210100000-8e44a81962b4227dbc32	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-6e21d81553cf048dcee3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2000900000-e3e2170131566f2c34e9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300100000-8e0fa01b9b99e8b1fea8	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0003900000-a08e1d1cb1452492cc40	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-2109100000-a099f262b4e99916ab71	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-0396000000-4a34a1ca0c2780791f62	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f79-0004900000-b7d25e9a9f2b33373222	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001u-4129500000-674f21af43f4a24fc9aa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f9y-9643100000-a3b87dfc44080a520c03	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x0000564abfcd51f8>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Phylum	Total species	Hosts and Body Sites	Microbial Links
Proteobacteria	182	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction
Firmicutes	391	Human Feces; Pig ; Human ; Cattle	Metabolic reconstruction
Actinobacteria	128	Human Feces; Human	Metabolic reconstruction
Verrucomicrobia	1	Human	Metabolic reconstruction
Bacteroidetes	126	Human Feces; Human	Metabolic reconstruction
Synergistetes	4	Human Feces	Metabolic reconstruction
Spirochaetes	1	Human Feces	Metabolic reconstruction
Thaumarchaeota	1	Human Feces	Metabolic reconstruction
Fusobacteria	20	Human Feces; Human	Metabolic reconstruction
Euryarchaeota	4	Human Feces; Cattle ; Human	Metabolic reconstruction
Candidatus Melainabacteria	1	Human Feces	Metabolic reconstruction
Tenericutes	4	Human Feces	Metabolic reconstruction
Planctomycetes	1	Human Feces	Metabolic reconstruction
Crenarchaeota	1	Human Feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB		details

External Links

HMDB ID

HMDB0001354

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022573

KNApSAcK ID

Not Available

Chemspider ID

559356

KEGG Compound ID

C00445

BioCyc ID

Not Available

BiGG ID

34999

Wikipedia Link

5,10-Methenyltetrahydrofolate

METLIN ID

6185

PubChem Compound

135450599

PDB ID

Not Available

ChEBI ID

15636

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Jahansouz H, Scherubel DM, Himes RH: Formylation of tetrahydrofolate by formyl phosphate. FEBS Lett. 1990 Mar 26;262(2):366-8. doi: 10.1016/0014-5793(90)80231-7. [PubMed:2335221 ]
Telegina TA, Liudnikova TA, Zemskova IuL, Sviridov EA, Kritskii MS: [Tolerance of 5,10-methenyltetrahydrofolate to ultraviolet radiation]. Prikl Biokhim Mikrobiol. 2005 May-Jun;41(3):315-23. [PubMed:15977793 ]
Field MS, Szebenyi DM, Stover PJ: Regulation of de novo purine biosynthesis by methenyltetrahydrofolate synthetase in neuroblastoma. J Biol Chem. 2006 Feb 17;281(7):4215-21. doi: 10.1074/jbc.M510624200. Epub 2005 Dec 19. [PubMed:16365037 ]
Moldt J, Pokorny R, Orth C, Linne U, Geisselbrecht Y, Marahiel MA, Essen LO, Batschauer A: Photoreduction of the folate cofactor in members of the photolyase family. J Biol Chem. 2009 Aug 7;284(32):21670-83. doi: 10.1074/jbc.M109.018697. Epub 2009 Jun 16. [PubMed:19531478 ]
Kruszyna L, Lianeri M, Rydzanicz M, Gajecka M, Szyfter K, Jagodzinski PP: Polymorphic variants of folate metabolism genes and the risk of laryngeal cancer. Mol Biol Rep. 2010 Jan;37(1):241-7. doi: 10.1007/s11033-009-9643-y. Epub 2009 Aug 1. [PubMed:19649727 ]
Kirsch SH, Knapp JP, Herrmann W, Obeid R: Quantification of key folate forms in serum using stable-isotope dilution ultra performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jan 1;878(1):68-75. doi: 10.1016/j.jchromb.2009.11.021. [PubMed:19959403 ]
Kariluoto S, Edelmann M, Herranen M, Lampi AM, Shmelev A, Salovaara H, Korhola M, Piironen V: Production of folate by bacteria isolated from oat bran. Int J Food Microbiol. 2010 Sep 30;143(1-2):41-7. doi: 10.1016/j.ijfoodmicro.2010.07.026. Epub 2010 Aug 11. [PubMed:20708290 ]
Knock E, Deng L, Krupenko N, Mohan RD, Wu Q, Leclerc D, Gupta S, Elmore CL, Kruger W, Tini M, Rozen R: Susceptibility to intestinal tumorigenesis in folate-deficient mice may be influenced by variation in one-carbon metabolism and DNA repair. J Nutr Biochem. 2011 Nov;22(11):1022-9. doi: 10.1016/j.jnutbio.2010.07.015. Epub 2010 Dec 28. [PubMed:21193302 ]
Ogwang S, Nguyen HT, Sherman M, Bajaksouzian S, Jacobs MR, Boom WH, Zhang GF, Nguyen L: Bacterial conversion of folinic acid is required for antifolate resistance. J Biol Chem. 2011 Apr 29;286(17):15377-90. doi: 10.1074/jbc.M111.231076. Epub 2011 Mar 3. [PubMed:21372133 ]
Lin CJ, Wen MJ, Hung YJ, Pei D, Kuo SW, Hsieh CH: The impact of 5,10-methenyltetrahydrofolate synthetase polymorphism on diabetic nephropathy in the Taiwanese population. Genet Test Mol Biomarkers. 2012 Feb;16(2):142-5. doi: 10.1089/gtmb.2011.0050. Epub 2011 Sep 6. [PubMed:21895484 ]
Oberpichler I, Pierik AJ, Wesslowski J, Pokorny R, Rosen R, Vugman M, Zhang F, Neubauer O, Ron EZ, Batschauer A, Lamparter T: A photolyase-like protein from Agrobacterium tumefaciens with an iron-sulfur cluster. PLoS One. 2011;6(10):e26775. doi: 10.1371/journal.pone.0026775. Epub 2011 Oct 31. [PubMed:22066008 ]
Eadsforth TC, Cameron S, Hunter WN: The crystal structure of Leishmania major N(5),N(10)-methylenetetrahydrofolate dehydrogenase/cyclohydrolase and assessment of a potential drug target. Mol Biochem Parasitol. 2012 Feb;181(2):178-85. doi: 10.1016/j.molbiopara.2011.11.004. Epub 2011 Nov 15. [PubMed:22108435 ]
Watkins D, Rosenblatt DS: Update and new concepts in vitamin responsive disorders of folate transport and metabolism. J Inherit Metab Dis. 2012 Jul;35(4):665-70. doi: 10.1007/s10545-011-9418-1. Epub 2011 Nov 23. [PubMed:22108709 ]
Selby CP, Sancar A: The second chromophore in Drosophila photolyase/cryptochrome family photoreceptors. Biochemistry. 2012 Jan 10;51(1):167-71. doi: 10.1021/bi201536w. Epub 2011 Dec 27. [PubMed:22175817 ]
Field MS, Anderson DD, Stover PJ: Mthfs is an Essential Gene in Mice and a Component of the Purinosome. Front Genet. 2011 Jun 20;2:36. doi: 10.3389/fgene.2011.00036. eCollection 2011. [PubMed:22303332 ]
Tolley M, Bickford L, Clare K, Johann TW: Investigations of amino acids in the ATP binding site of 5,10-methenyltetrahydrofolate synthetase. Protein J. 2012 Aug;31(6):519-28. doi: 10.1007/s10930-012-9428-3. [PubMed:22773193 ]
Upadhyay V, Demmer U, Warkentin E, Moll J, Shima S, Ermler U: Structure and catalytic mechanism of N(5),N(10)-methenyl-tetrahydromethanopterin cyclohydrolase. Biochemistry. 2012 Oct 23;51(42):8435-43. doi: 10.1021/bi300777k. Epub 2012 Oct 8. [PubMed:23013430 ]
Wijaya IM, Zhang Y, Iwata T, Yamamoto J, Hitomi K, Iwai S, Getzoff ED, Kandori H: Detection of distinct alpha-helical rearrangements of cyclobutane pyrimidine dimer photolyase upon substrate binding by Fourier transform infrared spectroscopy. Biochemistry. 2013 Feb 12;52(6):1019-27. doi: 10.1021/bi3016179. Epub 2013 Jan 30. [PubMed:23331252 ]

Showing metabocard for 5,10-Methenyltetrahydrofolic acid (MMDBc0031998)

MOL for #<Metabolite:0x0000564abaceb0c0>

3D MOL for #<Metabolite:0x0000564abaceb0c0>

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3D-SDF for #<Metabolite:0x0000564abaceb0c0>

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Structure for #<Metabolite:0x0000564abaceb0c0>

3D Structure for #<Metabolite:0x0000564abaceb0c0>