MiMeDB: Showing metabocard for UDP-N-acetyl-alpha-D-muramate (MMDBc0056358)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:23:39 UTC

Update Date

2022-08-12 20:09:42 UTC

Metabolite ID

MMDBc0056358

Metabolite Identification

Common Name

UDP-N-acetyl-alpha-D-muramate

Description

UDP-N-acetyl-alpha-D-muramate, also known as UDP-N-acetyl-a-D-muramate or UDP acetylmuramic acid, 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. Based on a literature review very few articles have been published on UDP-N-acetyl-alpha-D-muramate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222232D          

 54 56  0  0  1  0            999 V2000
    2.6215   12.3003    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
    3.4061   12.5552    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
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5777   13.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  2  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
    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  5  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  5  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
    2.9646   13.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  5  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
    2.7931   13.1073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   10.0922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   11.7483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1640    7.5531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   11.4512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    6.1103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6762   10.3893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    5.1739    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
  4  3  2  0  0  0  0
  7  1  1  6  0  0  0
  8  2  1  4  0  0  0
  9  5  1  1  0  0  0
 10  6  1  1  0  0  0
 11  3  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 19 12  1  0  0  0  0
 21  8  2  0  0  0  0
 12 21  1  6  0  0  0
 22 11  2  0  0  0  0
 22 20  1  0  0  0  0
 23  4  1  0  0  0  0
 17 23  1  1  0  0  0
 23 20  1  0  0  0  0
 24  5  1  0  0  0  0
 25  8  1  0  0  0  0
 26 11  1  0  0  0  0
 13 27  1  6  0  0  0
 14 28  1  6  0  0  0
 15 29  1  6  0  0  0
 30 18  2  0  0  0  0
 31 18  1  0  0  0  0
 32 20  2  0  0  0  0
 37  6  1  0  0  0  0
 38  7  1  0  0  0  0
 16 38  1  6  0  0  0
 39 10  1  0  0  0  0
 39 17  1  0  0  0  0
 40  9  1  0  0  0  0
 40 19  1  0  0  0  0
 19 41  1  6  0  0  0
 43 33  1  0  0  0  0
 43 34  2  0  0  0  0
 43 37  1  0  0  0  0
 43 42  1  0  0  0  0
 44 35  1  0  0  0  0
 44 36  2  0  0  0  0
 44 41  1  0  0  0  0
 44 42  1  0  0  0  0
  7 45  1  1  0  0  0
  9 46  1  6  0  0  0
 10 47  1  6  0  0  0
 12 48  1  1  0  0  0
 13 49  1  1  0  0  0
 14 50  1  1  0  0  0
 15 51  1  1  0  0  0
 16 52  1  6  0  0  0
 17 53  1  6  0  0  0
 19 54  1  1  0  0  0
M  CHG  3  25  -1  26  -1  31  -1
M  END


  Mrv1652306172222232D          

 54 56  0  0  1  0            999 V2000
    2.6215   12.3003    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
    3.4061   12.5552    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
   -1.8414    5.9090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5777   13.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   10.1343    0.0000 C   0  0  2  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
    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  5  0  0  0  0  0  0  0  0  0  0
   -3.7811    3.2393    0.0000 O   0  5  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
    2.9646   13.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3623   13.6171    0.0000 O   0  5  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
    2.7931   13.1073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0739   10.0922    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324    7.5085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346   11.7483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1640    7.5531    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323   11.4512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    6.1103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6762   10.3893    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669    5.1739    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
  4  3  2  0  0  0  0
  7  1  1  6  0  0  0
  8  2  1  4  0  0  0
  9  5  1  1  0  0  0
 10  6  1  1  0  0  0
 11  3  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  7  1  0  0  0  0
 19 12  1  0  0  0  0
 21  8  2  0  0  0  0
 12 21  1  6  0  0  0
 22 11  2  0  0  0  0
 22 20  1  0  0  0  0
 23  4  1  0  0  0  0
 17 23  1  1  0  0  0
 23 20  1  0  0  0  0
 24  5  1  0  0  0  0
 25  8  1  0  0  0  0
 26 11  1  0  0  0  0
 13 27  1  6  0  0  0
 14 28  1  6  0  0  0
 15 29  1  6  0  0  0
 30 18  2  0  0  0  0
 31 18  1  0  0  0  0
 32 20  2  0  0  0  0
 37  6  1  0  0  0  0
 38  7  1  0  0  0  0
 16 38  1  6  0  0  0
 39 10  1  0  0  0  0
 39 17  1  0  0  0  0
 40  9  1  0  0  0  0
 40 19  1  0  0  0  0
 19 41  1  6  0  0  0
 43 33  1  0  0  0  0
 43 34  2  0  0  0  0
 43 37  1  0  0  0  0
 43 42  1  0  0  0  0
 44 35  1  0  0  0  0
 44 36  2  0  0  0  0
 44 41  1  0  0  0  0
 44 42  1  0  0  0  0
  7 45  1  1  0  0  0
  9 46  1  6  0  0  0
 10 47  1  6  0  0  0
 12 48  1  1  0  0  0
 13 49  1  1  0  0  0
 14 50  1  1  0  0  0
 15 51  1  1  0  0  0
 16 52  1  6  0  0  0
 17 53  1  6  0  0  0
 19 54  1  1  0  0  0
M  CHG  3  25  -1  26  -1  31  -1
M  END
> <DATABASE_ID>
MMDBc0056358

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([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-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H31N3O19P2/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/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3/t7-,9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1

> <INCHI_KEY>
NQBRVZNDBBMBLJ-MQTLHLSBSA-K

> <FORMULA>
C20H28N3O19P2

> <MOLECULAR_WEIGHT>
676.395

> <EXACT_MASS>
676.080870429

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.53567999153826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.4076642866666678

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.051168107579656

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.728608492881233

> <JCHEM_PKA_STRONGEST_BASIC>
-3.647621074990214

> <JCHEM_POLAR_SURFACE_AREA>
342.18000000000006

> <JCHEM_REFRACTIVITY>
165.66790000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       4.894  22.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.964  22.009   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.621   7.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.716   8.377   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.151  17.332   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.043  12.971   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.358  23.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.109  20.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.007  18.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.421  12.495   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.153   7.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.718  20.424   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  13.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.327  19.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.913  12.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.182  20.900   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.437  11.030   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.678  24.943   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.398  18.917   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.874   9.945   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.573  21.454   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -6.779   8.699   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      -4.343   9.784   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       8.831  15.826   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.789  19.472   0.000  0.00  0.00           O-1
HETATM   26  O   UNK     0      -7.058   6.047   0.000  0.00  0.00           O-1
HETATM   27  O   UNK     0      -2.667  14.940   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.791  20.345   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.378  12.971   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.534  25.973   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.143  25.419   0.000  0.00  0.00           O-1
HETATM   32  O   UNK     0      -6.500  11.352   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.304  13.488   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.352  16.418   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.119  16.615   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.106  17.255   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.363  14.477   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       7.503  22.406   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.897  11.030   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       6.542  17.887   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       3.933  18.442   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       3.293  15.429   0.000  0.00  0.00           O+0
HETATM   43  P   UNK     0       1.828  14.953   0.000  0.00  0.00           P+0
HETATM   44  P   UNK     0       3.613  16.935   0.000  0.00  0.00           P+0
HETATM   45  H   UNK     0       5.214  24.467   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       9.471  18.839   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.181  14.016   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.038  21.930   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.040  14.099   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.647  21.376   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.002  11.406   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.862  19.393   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.738   9.658   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.253  19.948   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4   11                                                       
CONECT    4    3   23                                                       
CONECT    5    9   24                                                       
CONECT    6   10   37                                                       
CONECT    7    1   18   38   45                                             
CONECT    8    2   21   25                                                  
CONECT    9    5   14   40   46                                             
CONECT   10    6   13   39   47                                             
CONECT   11    3   22   26                                                  
CONECT   12   16   19   21   48                                             
CONECT   13   10   15   27   49                                             
CONECT   14    9   16   28   50                                             
CONECT   15   13   17   29   51                                             
CONECT   16   12   14   38   52                                             
CONECT   17   15   23   39   53                                             
CONECT   18    7   30   31                                                  
CONECT   19   12   40   41   54                                             
CONECT   20   22   23   32                                                  
CONECT   21    8   12                                                       
CONECT   22   11   20                                                       
CONECT   23    4   17   20                                                  
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26   11                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   18                                                            
CONECT   31   18                                                            
CONECT   32   20                                                            
CONECT   33   43                                                            
CONECT   34   43                                                            
CONECT   35   44                                                            
CONECT   36   44                                                            
CONECT   37    6   43                                                       
CONECT   38    7   16                                                       
CONECT   39   10   17                                                       
CONECT   40    9   19                                                       
CONECT   41   19   44                                                       
CONECT   42   43   44                                                       
CONECT   43   33   34   37   42                                             
CONECT   44   35   36   41   42                                             
CONECT   45    7                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   19                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

Synonyms

Value	Source
UDP-N-Acetyl-a-D-muramate	Generator
UDP-N-Acetyl-a-D-muramic acid	Generator
UDP-N-Acetyl-alpha-D-muramic acid	Generator
UDP-N-Acetyl-α-D-muramate	Generator
UDP-N-Acetyl-α-D-muramic acid	Generator
UDP Acetylmuramic acid	MeSH
Uridine diphosphate N acetylmuramic acid	MeSH
Acetylmuramic acid, UDP	MeSH
Acid, UDP acetylmuramic	MeSH
Uridine diphosphate N-acetylmuramic acid	MeSH

Molecular Formula

C₂₀H₂₈N₃O₁₉P₂

Average Mass

676.395

Monoisotopic Mass

676.080870429

IUPAC Name

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

Traditional Name

(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([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-])=O

InChI Identifier

InChI=1S/C20H31N3O19P2/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/h3-4,7,9-10,12-17,19,24,27-29H,5-6H2,1-2H3,(H,21,25)(H,30,31)(H,33,34)(H,35,36)(H,22,26,32)/p-3/t7-,9-,10-,12-,13-,14-,15-,16-,17-,19-/m1/s1

InChI Key

NQBRVZNDBBMBLJ-MQTLHLSBSA-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
Muramic_acid
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Sugar acid
Alkyl phosphate
Phosphoric acid ester
Oxane
Hydropyrimidine
Organic phosphoric acid derivative
Pyrimidine
Monosaccharide
Heteroaromatic compound
Acetamide
Vinylogous amide
Tetrahydrofuran
Carboxamide group
Lactam
Urea
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
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

UDP-N-acetylmuramate(3-) (CHEBI:70757 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.4	ChemAxon
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	342.18 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	165.67 m³·mol⁻¹	ChemAxon
Polarizability	55.54 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	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	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	Cyanobacteria	27	Human
Bacteria	Firmicutes	156	Human ; Human feces; Catfish ; Cattle ; Human subgingival plaque; Human saliva
Bacteria	Proteobacteria	402	Human ; Cattle ; Human feces; Rat ; Sheep ; Pig ; Chicken ; American dog tick ; River trout ; Turkey
Bacteria	Bacteroidetes	13	Human ; Human feces
Bacteria	Aquificae	4
Bacteria	Spirochaetes	11	Human ; Pig
Bacteria	Chloroflexi	5
Bacteria	Chlamydiae	10	Human ; Sheep ; Cat
Bacteria	Chlorobi	11
Bacteria	Actinobacteria	56	Human ; Human feces; Cattle
Bacteria	Deinococcus-thermus	4
Bacteria	Thermotogae	8
Bacteria	Fusobacteria	1	Human ; Human feces
Bacteria	Planctomycetes	1
Bacteria	Acidobacteria	3
Bacteria	nah	1
Bacteria	Dictyoglomi	2
Bacteria	Elusimicrobia	1

Exposure Sources

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

28533296

KEGG Compound ID

Not Available

BioCyc ID

UDP-N-ACETYLMURAMATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24772978

PDB ID

Not Available

ChEBI ID

70757

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-muramate (MMDBc0056358)

MOL for #<Metabolite:0x00007fdb4d96af98>

3D MOL for #<Metabolite:0x00007fdb4d96af98>

3D SDF for #<Metabolite:0x00007fdb4d96af98>

3D-SDF for #<Metabolite:0x00007fdb4d96af98>

PDB for #<Metabolite:0x00007fdb4d96af98>

3D PDB for #<Metabolite:0x00007fdb4d96af98>

SMILES for #<Metabolite:0x00007fdb4d96af98>

INCHI for #<Metabolite:0x00007fdb4d96af98>

Structure for #<Metabolite:0x00007fdb4d96af98>

3D Structure for #<Metabolite:0x00007fdb4d96af98>