MiMeDB: Showing metabocard for UDP-N-acetyl-Œ±-D-glucosamine-enolpyruvate (MMDBc0032157)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:04:46 UTC

Update Date

2022-08-31 18:30:58 UTC

MiMeDB ID

MMDBc0032157

Metabolite Identification

Common Name

UDP-N-acetyl-Œ±-D-glucosamine-enolpyruvate

Description

UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate is an intermediate in UDP-N-acetylmuramoyl-pentapeptide biosynthesis I (meso-DAP-containing) pathway in E.coli. It is a substrate for the enzyme UDP-N-acetylenolpyruvoylglucosamine reductase which catalyzes the reaction UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate + NADPH + H+ -> UDP-N-acetyl-alpha-D-muramate + NADP+. It is also a product for enzyme UDP-N-acetylglucosamine enolpyruvoyl transferase which catalyzes reaction UDP-N-acetyl-alpha-D-glucosamine + phosphoenolpyruvate -> UDP-N-acetyl-Œ±-D-glucosamine-enolpyruvate + phosphate (BioCyc compound: UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005041519042D          

 44 46  0  0  0  0            999 V2000
   -2.6050    3.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    4.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    5.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817    4.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    3.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    2.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    1.7634    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6653    2.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    1.0489    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9673    1.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    0.5259    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923    0.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1423    0.5259    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9673   -0.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -0.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -2.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942   -2.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -2.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7843   -3.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143   -2.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297   -1.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -3.4735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -3.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490   -4.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -5.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -4.8946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -4.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -4.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    3.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    3.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    1.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    1.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    4.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    5.4759    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 27  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 29 35  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
  4 37  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  CHG  3  15  -1  19  -1  44  -1
M  END


  Mrv1533005041519042D          

 44 46  0  0  0  0            999 V2000
   -2.6050    3.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    4.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    5.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    4.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817    4.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    3.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    3.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4616    2.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2528    1.7634    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6653    2.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1596    1.0489    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9673    1.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673    0.5259    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923    0.5259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1423    0.5259    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9673   -0.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -0.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6817   -1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -2.0215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942   -2.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692   -2.8061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7843   -3.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0143   -2.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2297   -1.7665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5792   -3.4735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3996   -3.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5490   -4.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339   -5.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -4.8946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436   -4.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4231   -4.3134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    3.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    3.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    1.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    1.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    4.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0339    4.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    5.4759    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 27  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 29 35  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
  4 37  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  CHG  3  15  -1  19  -1  44  -1
M  END
> <DATABASE_ID>
MMDBc0032157

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NC1C(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)OC(CO)C(O)C1OC(=C)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3

> <INCHI_KEY>
BEGZZYPUNCJHKP-UHFFFAOYSA-K

> <FORMULA>
C20H26N3O19P2

> <MOLECULAR_WEIGHT>
674.379

> <EXACT_MASS>
674.065220365

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.43312737361601

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]prop-2-enoate

> <ALOGPS_LOGP>
-0.98

> <JCHEM_LOGP>
-4.638949203

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.037885392048719

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7303240065452128

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6465870252254513

> <JCHEM_POLAR_SURFACE_AREA>
335.19999999999993

> <JCHEM_REFRACTIVITY>
141.8995

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-15         0                                  
HETATM    1  C   UNK     0      -4.863   6.372   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.863   7.912   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.529   8.682   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.195   7.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.862   8.682   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.862  10.222   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.472   7.912   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.806   8.682   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.139   7.912   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.472   6.372   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.862   5.602   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.862   4.062   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       0.472   3.292   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0       1.242   4.625   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.298   1.958   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0       1.806   2.522   0.000  0.00  0.00           O+0
HETATM   17  P   UNK     0       1.806   0.982   0.000  0.00  0.00           P+0
HETATM   18  O   UNK     0       3.346   0.982   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.266   0.982   0.000  0.00  0.00           O-1
HETATM   20  O   UNK     0       1.806  -0.558   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.139  -1.328   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.139  -2.868   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.385  -3.773   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.909  -5.238   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.369  -5.238   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.464  -6.484   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.893  -3.773   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.429  -3.297   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       4.815  -6.484   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.346  -6.323   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.251  -7.569   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.625  -8.976   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.530 -10.222   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       5.093  -9.137   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.188  -7.891   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.656  -8.052   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.195   6.372   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -3.529   5.602   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -3.529   4.062   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.195   3.292   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.863   3.292   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.196   8.682   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -7.530   7.912   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -6.196  10.222   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   22                                                  
CONECT   28   27                                                            
CONECT   29   24   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   29                                                  
CONECT   36   35                                                            
CONECT   37   11   38    4                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42    2   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

Synonyms

Value	Source
UDP-N-Acetyl-α-D-glucosamine-enolpyruvic acid	Generator

Chemical Formula

C₂₀H₂₆N₃O₁₉P₂

Average Molecular Weight

674.379

Monoisotopic Molecular Weight

674.065220365

IUPAC Name

2-[(2-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl)oxy]prop-2-enoate

Traditional Name

2-({2-[({[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)NC1C(OP([O-])(=O)OP([O-])(=O)OCC2OC(C(O)C2O)N2C=CC(=O)NC2=O)OC(CO)C(O)C1OC(=C)C([O-])=O

InChI Identifier

InChI=1S/C20H29N3O19P2/c1-7(18(30)31)38-16-12(21-8(2)25)19(40-9(5-24)14(16)28)41-44(35,36)42-43(33,34)37-6-10-13(27)15(29)17(39-10)23-4-3-11(26)22-20(23)32/h3-4,9-10,12-17,19,24,27-29H,1,5-6H2,2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3

InChI Key

BEGZZYPUNCJHKP-UHFFFAOYSA-K

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-5-phosphate
Pentose phosphate
N-acyl-alpha-hexosamine
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
Pyrimidone
Sugar acid
Oxane
Pyrimidine
Phosphoric acid ester
Hydropyrimidine
Alkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Heteroaromatic compound
Acetamide
Vinylogous amide
Tetrahydrofuran
Lactam
Urea
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a UDP-sugar (UDP-ACETYL-CARBOXYVINYL-GLUCOSAMINE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	16.7 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-4.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	335.2 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	141.9 m³·mol⁻¹	ChemAxon
Polarizability	55.43 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000009000-c7038eb4ed6123137d5c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-1001009000-0a0565ac6231b8e384b7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9421003000-8a3b2c5ad565ff610ca7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-7000009000-2144809f24d0816ffe51	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9100003000-25052929b8f62b948432	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9300000000-d989f93239b8508b2014	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

Not Available

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

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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-acetyl-Œ±-D-glucosamine-enolpyruvate (MMDBc0032157)

MOL for #<Metabolite:0x000055b76bd4fe40>

3D MOL for #<Metabolite:0x000055b76bd4fe40>

3D SDF for #<Metabolite:0x000055b76bd4fe40>

3D-SDF for #<Metabolite:0x000055b76bd4fe40>

PDB for #<Metabolite:0x000055b76bd4fe40>

3D PDB for #<Metabolite:0x000055b76bd4fe40>

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INCHI for #<Metabolite:0x000055b76bd4fe40>

Structure for #<Metabolite:0x000055b76bd4fe40>

3D Structure for #<Metabolite:0x000055b76bd4fe40>