MiMeDB: Showing metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanine (MMDBc0054690)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:24:34 UTC

Update Date

2022-08-12 20:09:03 UTC

Metabolite ID

MMDBc0054690

Metabolite Identification

Common Name

UDP-N-acetyl-alpha-D-muramoyl-L-alanine

Description

Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine, also known as UDP-N-acetyl-a-D-muramoyl-L-alanine, 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. Uridine-5'-Diphosphate-N-Acetylmuramoyl-L-Alanine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07171215202D          
 
 49 51  0  0  1  0            999 V2000
   20.7702  -12.4705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.7702  -13.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0482  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4853  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0482  -13.7200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5809  -14.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3368  -12.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.3100  -12.0599    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3368  -13.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0482  -14.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5809  -14.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6254  -12.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1312  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3100  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3100  -12.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6217  -13.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3332  -14.9554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2959  -15.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8694  -15.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6183  -11.2103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9524  -12.0599    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3296  -15.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6217  -14.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7807  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9560  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9524  -12.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4235  -16.4809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0412  -16.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9577  -12.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4129  -17.2950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.7399  -13.1183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6236  -17.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1066  -17.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3948  -12.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0054  -13.9005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9475  -17.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6236  -18.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0709  -13.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8231  -13.9005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5241  -14.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7150  -11.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3151  -14.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0036  -11.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4372  -11.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0036  -10.5343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2886  -11.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4372  -10.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7186  -10.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7150   -9.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7 12  1  1  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  2  0  0  0  0
  9 16  1  6  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 11 19  2  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  1  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
 24 29  1  0  0  0  0
 30 27  1  1  0  0  0
 31 29  1  1  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 34  1  0  0  0  0
 31 35  1  0  0  0  0
 32 36  1  0  0  0  0
 32 37  2  0  0  0  0
 34 38  1  0  0  0  0
 35 39  1  0  0  0  0
 35 40  1  6  0  0  0
 38 41  1  1  0  0  0
 39 42  1  6  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  2  0  0  0  0
 44 47  2  0  0  0  0
 45 48  1  0  0  0  0
 48 49  2  0  0  0  0
  7  9  1  0  0  0  0
 38 39  1  0  0  0  0
 47 48  1  0  0  0  0
M  END

 
  Mrv0541 07171215202D          
 
 49 51  0  0  1  0            999 V2000
   20.7702  -12.4705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.7702  -13.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0482  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4853  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0482  -13.7200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.5809  -14.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3368  -12.4705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.3100  -12.0599    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3368  -13.3024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.0482  -14.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5809  -14.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6254  -12.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1312  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3100  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3100  -12.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6217  -13.7094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3332  -14.9554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2959  -15.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8694  -15.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6183  -11.2103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9524  -12.0599    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.3296  -15.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6217  -14.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7807  -12.0599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9560  -11.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9524  -12.8811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4235  -16.4809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0412  -16.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9577  -12.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4129  -17.2950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.7399  -13.1183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6236  -17.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1066  -17.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3948  -12.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0054  -13.9005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9475  -17.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6236  -18.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0709  -13.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.8231  -13.9005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.5241  -14.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7150  -11.7908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3151  -14.5660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0036  -11.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4372  -11.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0036  -10.5343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2886  -11.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4372  -10.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7186  -10.1237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7150   -9.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  6  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7 12  1  1  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  2  0  0  0  0
  9 16  1  6  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 11 19  2  0  0  0  0
 12 20  1  0  0  0  0
 13 21  1  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  1  0  0  0
 21 24  1  0  0  0  0
 21 25  1  0  0  0  0
 21 26  2  0  0  0  0
 22 27  1  0  0  0  0
 22 28  2  0  0  0  0
 24 29  1  0  0  0  0
 30 27  1  1  0  0  0
 31 29  1  1  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 34  1  0  0  0  0
 31 35  1  0  0  0  0
 32 36  1  0  0  0  0
 32 37  2  0  0  0  0
 34 38  1  0  0  0  0
 35 39  1  0  0  0  0
 35 40  1  6  0  0  0
 38 41  1  1  0  0  0
 39 42  1  6  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  2  0  0  0  0
 44 47  2  0  0  0  0
 45 48  1  0  0  0  0
 48 49  2  0  0  0  0
  7  9  1  0  0  0  0
 38 39  1  0  0  0  0
 47 48  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054690

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)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-KBKUWGQMSA-N

> <FORMULA>
C23H36N4O20P2

> <MOLECULAR_WEIGHT>
750.4943

> <EXACT_MASS>
750.139812636

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
64.86466223735499

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-5.131288215333333

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.9989498970627873

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7295427641153935

> <JCHEM_PKA_STRONGEST_BASIC>
-3.664543362841415

> <JCHEM_POLAR_SURFACE_AREA>
355.80999999999995

> <JCHEM_REFRACTIVITY>
150.1842

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-12         0                                  
HETATM    1  C   UNK     0      38.771 -23.278   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      38.771 -24.831   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      37.423 -22.512   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      40.106 -22.512   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      37.423 -25.611   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      40.284 -26.225   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      36.095 -23.278   0.000  0.00  0.00           C+0
HETATM    8  P   UNK     0      41.645 -22.512   0.000  0.00  0.00           P+0
HETATM    9  C   UNK     0      36.095 -24.831   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      37.423 -27.157   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      40.284 -27.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.767 -22.512   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      43.178 -22.512   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      41.645 -20.972   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      41.645 -24.045   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      34.761 -25.591   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      36.089 -27.917   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.619 -28.531   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      38.956 -28.538   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      34.754 -20.926   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      44.711 -22.512   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      36.082 -29.456   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      34.761 -27.150   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      46.257 -22.512   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      44.718 -20.972   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      44.711 -24.045   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      34.391 -30.764   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0      37.410 -30.223   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      46.588 -24.018   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.371 -32.284   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      48.048 -24.487   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.897 -32.786   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      35.666 -33.156   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      49.270 -23.589   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      48.543 -25.948   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      31.635 -31.894   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      32.897 -34.326   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      50.532 -24.514   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      50.070 -25.948   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      47.645 -27.197   0.000  0.00  0.00           O+0
HETATM   41  N   UNK     0      51.735 -22.010   0.000  0.00  0.00           N+0
HETATM   42  O   UNK     0      50.988 -27.190   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      50.407 -21.223   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      53.083 -21.223   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      50.407 -19.664   0.000  0.00  0.00           N+0
HETATM   46  O   UNK     0      49.072 -21.983   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      53.083 -19.664   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      51.741 -18.898   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      51.735 -17.371   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12    9                                                  
CONECT    8    4   13   14   15                                             
CONECT    9    5   16    7                                                  
CONECT   10    5   17                                                       
CONECT   11    6   18   19                                                  
CONECT   12    7   20                                                       
CONECT   13    8   21                                                       
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10   22   23                                                  
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13   24   25   26                                             
CONECT   22   17   27   28                                                  
CONECT   23   17                                                            
CONECT   24   21   29                                                       
CONECT   25   21                                                            
CONECT   26   21                                                            
CONECT   27   22   30                                                       
CONECT   28   22                                                            
CONECT   29   24   31                                                       
CONECT   30   27   32   33                                                  
CONECT   31   29   34   35                                                  
CONECT   32   30   36   37                                                  
CONECT   33   30                                                            
CONECT   34   31   38                                                       
CONECT   35   31   39   40                                                  
CONECT   36   32                                                            
CONECT   37   32                                                            
CONECT   38   34   41   39                                                  
CONECT   39   35   42   38                                                  
CONECT   40   35                                                            
CONECT   41   38   43   44                                                  
CONECT   42   39                                                            
CONECT   43   41   45   46                                                  
CONECT   44   41   47                                                       
CONECT   45   43   48                                                       
CONECT   46   43                                                            
CONECT   47   44   48                                                       
CONECT   48   45   49   47                                                  
CONECT   49   48                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

Synonyms

Value	Source
UDP-N-Acetylmuramoyl-L-alanine	ChEBI
UDP-N-Acetyl-alpha-D-muramoyl-L-alanine	Kegg
UDP-N-Acetyl-a-D-muramoyl-L-alanine	Generator
UDP-N-Acetyl-α-D-muramoyl-L-alanine	Generator
Uridine-5'-diphosphoric acid-N-acetylmuramoyl-L-alanine	Generator
Uridine-5'-diphosphate-N-acetylmuramoyl-L-alanine	ChEBI

Molecular Formula

C₂₃H₃₆N₄O₂₀P₂

Average Mass

750.4943

Monoisotopic Mass

750.139812636

IUPAC Name

(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid

Traditional Name

(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@@H]1NC(C)=O)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-KBKUWGQMSA-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

UDP-N-acetylmuramoyl-L-alanine (CHEBI:84726 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	9.58 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-5.1	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	355.81 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	150.18 m³·mol⁻¹	ChemAxon
Polarizability	64.86 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_15) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-5900000200-c2f83a9ff1ba6236dd04	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-5901000000-2d5430732c7560f2988f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03du-9400000000-120ee449c111c29951b8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-7914302500-06c16b9345cdb58676e3	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06rx-9602020200-c5bbe24eea4d6dde55c0	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5912000000-0e78ecc1e26746abf27e	2017-07-26	View 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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria/Eubacteria	Cyanobacteria	30	Human
Bacteria/Eubacteria	Firmicutes	161	Human feces; Human ; Cattle ; Human subgingival plaque; Human saliva; Catfish
Bacteria/Eubacteria	Proteobacteria	394	Human ; Human feces; Cattle ; Turkey ; Pig ; Sheep ; Chicken ; River trout ; Rat ; American dog tick
Bacteria/Eubacteria	Acidobacteria	3
Bacteria/Eubacteria	Aquificae	4
Bacteria/Eubacteria	Bacteroidetes	12	Human ; Human feces
Bacteria/Eubacteria	Actinobacteria	56	Human ; Human feces; Cattle
Bacteria/Eubacteria	Spirochaetes	11	Human ; Pig
Bacteria/Eubacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria/Eubacteria	Chlorobi	11
Bacteria/Eubacteria	Deinococcus-thermus	4
Bacteria	Proteobacteria	5	Human ; Human feces; Cattle ; Turkey ; Pig ; Sheep ; Chicken ; River trout ; Rat ; American dog tick
Bacteria/Eubacteria	Elusimicrobia	2
Bacteria/Eubacteria	Thermotogae	9
Bacteria/Eubacteria	Fusobacteria	1	Human ; Human feces
Bacteria/Eubacteria	Chloroflexi	4
Bacteria	nah	1
Bacteria/Eubacteria	Dictyoglomi	2
Bacteria	Actinobacteria	1	Human ; Human feces; Cattle

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

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

DB01673

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C01212

BioCyc ID

CPD0-1456

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5496796

PDB ID

Not Available

ChEBI ID

84726

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for UDP-N-acetyl-alpha-D-muramoyl-L-alanine (MMDBc0054690)

MOL for #<Metabolite:0x00007f7a902f5348>

3D MOL for #<Metabolite:0x00007f7a902f5348>

3D SDF for #<Metabolite:0x00007f7a902f5348>

3D-SDF for #<Metabolite:0x00007f7a902f5348>

PDB for #<Metabolite:0x00007f7a902f5348>

3D PDB for #<Metabolite:0x00007f7a902f5348>

SMILES for #<Metabolite:0x00007f7a902f5348>

INCHI for #<Metabolite:0x00007f7a902f5348>

Structure for #<Metabolite:0x00007f7a902f5348>

3D Structure for #<Metabolite:0x00007f7a902f5348>