MiMeDB: Showing metabocard for UDP-N-Acetylmuramoyl-L-alanine (MMDBc0029815)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:42:53 UTC

Update Date

2022-08-31 17:18:45 UTC

MiMeDB ID

MMDBc0029815

Metabolite Identification

Common Name

UDP-N-Acetylmuramoyl-L-alanine

Description

Udp-n-acetylmuramoyl-l-alanine belongs to the class of Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. (inferred from compound structure)UDP-N-acetylmuramoyl-L-alanine (UDP-MurNAc-L-Ala), which is the nucleotide substrate of the D-glutamic-acid-adding enzyme (the murD gene product) catalyzing the subsequent step in the pathway for peptidoglycan synthesis, appears to be an effector of the racemase activity. (PMID 8098327 ) MurD (UDP-N-acetylmuramoyl-L-alanine:D-glutamate ligase) is the second enzyme in the series of Mur ligases, and it catalyzes the addition of D-glutamic acid (D-Glu) to the cytoplasmic intermediate UDP-N-acetylmuramoyl-L-alanine (UMA). (PMID 19007109 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10231213462D          

 60 62  0  0  0  0            999 V2000
    5.3184   14.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   11.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   11.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315   14.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8039   12.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6654   11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9754   13.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7162   14.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   13.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308    8.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   10.4314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8877   15.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293   13.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031   14.9340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   12.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   10.3451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9483   11.7583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   10.3351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   11.9247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 10  3  1  4  0  0  0
 11  6  1  1  0  0  0
 12  7  1  1  0  0  0
 13  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 22 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  2  0  0  0  0
 14 25  1  6  0  0  0
 26 13  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 20 27  1  1  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 29 10  1  0  0  0  0
 30 13  1  0  0  0  0
 15 31  1  6  0  0  0
 16 32  1  6  0  0  0
 17 33  1  6  0  0  0
 19 34  1  4  0  0  0
 35 21  2  0  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 42  7  1  0  0  0  0
 43  9  1  0  0  0  0
 18 43  1  1  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 11  1  0  0  0  0
 45 22  1  0  0  0  0
 46 22  1  0  0  0  0
 48 38  1  0  0  0  0
 48 39  2  0  0  0  0
 48 42  1  0  0  0  0
 48 47  1  0  0  0  0
 49 40  1  0  0  0  0
 49 41  2  0  0  0  0
 49 46  1  0  0  0  0
 49 47  1  0  0  0  0
  8 50  1  6  0  0  0
  9 51  1  6  0  0  0
 11 52  1  6  0  0  0
 12 53  1  6  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 17 57  1  1  0  0  0
 18 58  1  6  0  0  0
 20 59  1  6  0  0  0
 60 22  1  0  0  0  0
M  END


  Mrv0541 10231213462D          

 60 62  0  0  0  0            999 V2000
    5.3184   14.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4170   11.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   11.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4757    3.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9908    4.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024    9.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    6.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315   14.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8039   12.2581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6654   11.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2893    9.8372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7615    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2962    3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631   10.9413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    7.1786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4608   10.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0964    6.6937    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8477   11.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9754   13.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7162   14.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468    5.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   13.3201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4500   11.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    4.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264    5.2416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308    8.4782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938   10.4314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   10.8991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8810    6.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8877   15.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293   13.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4824    6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    7.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243    8.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    8.9009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    9.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946    7.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   12.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    5.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5047    9.5823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1069    9.8794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    8.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793    8.0105    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    9.0724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031   14.9340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   12.5131    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   10.3451    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9189    7.5035    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9483   11.7583    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8663    7.7819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   10.3351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   11.9247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    6.0381    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785   10.6864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  1  0  0  0
  9  2  1  1  0  0  0
 10  3  1  4  0  0  0
 11  6  1  1  0  0  0
 12  7  1  1  0  0  0
 13  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 22 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 19  2  0  0  0  0
 25 10  2  0  0  0  0
 14 25  1  6  0  0  0
 26 13  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 20 27  1  1  0  0  0
 27 23  1  0  0  0  0
 28  6  1  0  0  0  0
 29 10  1  0  0  0  0
 30 13  1  0  0  0  0
 15 31  1  6  0  0  0
 16 32  1  6  0  0  0
 17 33  1  6  0  0  0
 19 34  1  4  0  0  0
 35 21  2  0  0  0  0
 36 21  1  0  0  0  0
 37 23  2  0  0  0  0
 42  7  1  0  0  0  0
 43  9  1  0  0  0  0
 18 43  1  1  0  0  0
 44 12  1  0  0  0  0
 44 20  1  0  0  0  0
 45 11  1  0  0  0  0
 45 22  1  0  0  0  0
 46 22  1  0  0  0  0
 48 38  1  0  0  0  0
 48 39  2  0  0  0  0
 48 42  1  0  0  0  0
 48 47  1  0  0  0  0
 49 40  1  0  0  0  0
 49 41  2  0  0  0  0
 49 46  1  0  0  0  0
 49 47  1  0  0  0  0
  8 50  1  6  0  0  0
  9 51  1  6  0  0  0
 11 52  1  6  0  0  0
 12 53  1  6  0  0  0
 14 54  1  1  0  0  0
 15 55  1  1  0  0  0
 16 56  1  1  0  0  0
 17 57  1  1  0  0  0
 18 58  1  6  0  0  0
 20 59  1  6  0  0  0
 60 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029815

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=N[C@@]([H])(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/t8-,9+,11+,12+,14+,15+,16+,17+,18+,20+,22?/m0/s1

> <INCHI_KEY>
NTMMCWJNQNKACG-CPDMUANVSA-N

> <FORMULA>
C23H36N4O20P2

> <MOLECULAR_WEIGHT>
750.4943

> <EXACT_MASS>
750.139812636

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
64.63361918815096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2R)-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid

> <ALOGPS_LOGP>
-1.26

> <JCHEM_LOGP>
-3.1245791570000003

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.986712278153094

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7263620426244408

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6645543264939358

> <JCHEM_POLAR_SURFACE_AREA>
366.2800000000001

> <JCHEM_REFRACTIVITY>
151.54929999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2R)-2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   48  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   49  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   50  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5   13                                                       
CONECT    5    4   27                                                       
CONECT    6   11   28                                                       
CONECT    7   12   42                                                       
CONECT    8    1   21   24   50                                             
CONECT    9    2   19   43   51                                             
CONECT   10    3   25   29                                                  
CONECT   11    6   16   45   52                                             
CONECT   12    7   15   44   53                                             
CONECT   13    4   26   30                                                  
CONECT   14   18   22   25   54                                             
CONECT   15   12   17   31   55                                             
CONECT   16   11   18   32   56                                             
CONECT   17   15   20   33   57                                             
CONECT   18   14   16   43   58                                             
CONECT   19    9   24   34                                                  
CONECT   20   17   27   44   59                                             
CONECT   21    8   35   36                                                  
CONECT   22   14   45   46   60                                             
CONECT   23   26   27   37                                                  
CONECT   24    8   19                                                       
CONECT   25   10   14                                                       
CONECT   26   13   23                                                       
CONECT   27    5   20   23                                                  
CONECT   28    6                                                            
CONECT   29   10                                                            
CONECT   30   13                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   19                                                            
CONECT   35   21                                                            
CONECT   36   21                                                            
CONECT   37   23                                                            
CONECT   38   48                                                            
CONECT   39   48                                                            
CONECT   40   49                                                            
CONECT   41   49                                                            
CONECT   42    7   48                                                       
CONECT   43    9   18                                                       
CONECT   44   12   20                                                       
CONECT   45   11   22                                                       
CONECT   46   22   49                                                       
CONECT   47   48   49                                                       
CONECT   48   38   39   42   47                                             
CONECT   49   40   41   46   47                                             
CONECT   50    8                                                            
CONECT   51    9                                                            
CONECT   52   11                                                            
CONECT   53   12                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   17                                                            
CONECT   58   18                                                            
CONECT   59   20                                                            
CONECT   60   22                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

Synonyms

Not Available

Chemical Formula

C₂₃H₃₆N₄O₂₀P₂

Average Molecular Weight

750.4943

Monoisotopic Molecular Weight

750.139812636

IUPAC Name

(2S)-2-{[(2R)-2-{[(3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid

Traditional Name

(2S)-2-{[(2R)-2-{[(3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene]amino}propanoic acid

CAS Registry Number

78738-65-5

SMILES

[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=N[C@@]([H])(C)C(O)=O

InChI Identifier

InChI=1S/C23H36N4O20P2/c1-8(21(35)36)24-19(34)9(2)43-18-14(25-10(3)29)22(45-11(6-28)16(18)32)46-49(40,41)47-48(38,39)42-7-12-15(31)17(33)20(44-12)27-5-4-13(30)26-23(27)37/h4-5,8-9,11-12,14-18,20,22,28,31-33H,6-7H2,1-3H3,(H,24,34)(H,25,29)(H,35,36)(H,38,39)(H,40,41)(H,26,30,37)/t8-,9+,11+,12+,14+,15+,16+,17+,18+,20+,22?/m0/s1

InChI Key

NTMMCWJNQNKACG-CPDMUANVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Glycosyl compound
N-glycosyl compound
Alanine or derivatives
Alpha-amino acid or derivatives
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Hydropyrimidine
Oxane
Monosaccharide
Organic phosphoric acid derivative
Tetrahydrofuran
Vinylogous amide
Acetamide
Heteroaromatic compound
Secondary carboxylic acid amide
Secondary alcohol
Urea
Carboxamide group
Lactam
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Primary alcohol
Organooxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glyco-amino acid (CHEBI:16932 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	17.3 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-3.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	366.28 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	151.55 m³·mol⁻¹	ChemAxon
Polarizability	64.63 Å³	ChemAxon
Number of Rings	3	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 (TMS_2_11) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-5900000200-10c08e7fa5be20ae1807	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-5900000000-c709a71b4651bce45ce7	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03du-9400000000-c0d9160051e7f7f2b7a0	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-8914303600-11b64513dcd6d6c45ba1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08gl-9713130300-9485d5c1d45c8be86f5b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5912000000-6bffb4709eadd4c8f246	2015-09-15	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

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

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	174	Human Feces; Human ; Pig	Unknown; Metabolic reconstruction
Firmicutes	369	Human Feces; Pig ; Human ; Cattle	Metabolic reconstruction
Actinobacteria	119	Human Feces; Human	Metabolic reconstruction
Verrucomicrobia	1	Human	Metabolic reconstruction
Bacteroidetes	116	Human Feces; Human	Metabolic reconstruction
Synergistetes	3	Human Feces	Metabolic reconstruction
Spirochaetes	1	Human Feces	Metabolic reconstruction
Thaumarchaeota	1	Human Feces	Metabolic reconstruction
Fusobacteria	19	Human Feces; Human	Metabolic reconstruction
Euryarchaeota	5	Human Feces; Cattle ; Human	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3037124

PDB ID

Not Available

ChEBI ID

16932

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for UDP-N-Acetylmuramoyl-L-alanine (MMDBc0029815)

MOL for #<Metabolite:0x000055b76df9cf48>

3D MOL for #<Metabolite:0x000055b76df9cf48>

3D SDF for #<Metabolite:0x000055b76df9cf48>

3D-SDF for #<Metabolite:0x000055b76df9cf48>

PDB for #<Metabolite:0x000055b76df9cf48>

3D PDB for #<Metabolite:0x000055b76df9cf48>

SMILES for #<Metabolite:0x000055b76df9cf48>

INCHI for #<Metabolite:0x000055b76df9cf48>

Structure for #<Metabolite:0x000055b76df9cf48>

3D Structure for #<Metabolite:0x000055b76df9cf48>