MiMeDB: Showing metabocard for UDP-N-acetyl-alpha-D-mannosamine (MMDBc0056357)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:23:38 UTC

Update Date

2022-08-12 20:09:42 UTC

Metabolite ID

MMDBc0056357

Metabolite Identification

Common Name

UDP-N-acetyl-alpha-D-mannosamine

Description

UDP-N-acetyl-alpha-D-mannosamine(2-), also known as UDP-N-acetyl-a-D-mannosamine or uridine diphosphate N-acetylmannosamine, 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-mannosamine(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222232D          

 48 50  0  0  1  0            999 V2000
    2.0084   12.8523    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
    2.6215   12.3003    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  1  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
   -1.4289    7.1786    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
   -2.0964    6.6937    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
    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
    3.4061   12.5552    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
    5.2454   10.8991    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
    4.0192   12.0032    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
   -3.4824    6.0815    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
    1.2342    7.2259    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
    2.7424    8.9009    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
   -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
    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
    4.6323   11.4512    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
    3.6762   10.3893    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
   -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
  3  2  2  0  0  0  0
  6  1  1  4  0  0  0
  7  4  1  1  0  0  0
  8  5  1  1  0  0  0
  9  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 18  6  2  0  0  0  0
 10 18  1  1  0  0  0
 19  9  2  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  0  0  0  0
 15 20  1  1  0  0  0
 20 17  1  0  0  0  0
 21  4  1  0  0  0  0
 22  6  1  0  0  0  0
 23  9  1  0  0  0  0
 11 24  1  6  0  0  0
 12 25  1  6  0  0  0
 13 26  1  6  0  0  0
 14 27  1  6  0  0  0
 28 17  2  0  0  0  0
 33  5  1  0  0  0  0
 34  8  1  0  0  0  0
 34 15  1  0  0  0  0
 35  7  1  0  0  0  0
 35 16  1  0  0  0  0
 16 36  1  6  0  0  0
 38 29  1  0  0  0  0
 38 30  2  0  0  0  0
 38 33  1  0  0  0  0
 38 37  1  0  0  0  0
 39 31  1  0  0  0  0
 39 32  2  0  0  0  0
 39 36  1  0  0  0  0
 39 37  1  0  0  0  0
  7 40  1  6  0  0  0
  8 41  1  6  0  0  0
 10 42  1  6  0  0  0
 11 43  1  1  0  0  0
 12 44  1  1  0  0  0
 13 45  1  6  0  0  0
 14 46  1  1  0  0  0
 15 47  1  6  0  0  0
 16 48  1  1  0  0  0
M  CHG  2  22  -1  23  -1
M  END


  Mrv1652306172222232D          

 48 50  0  0  1  0            999 V2000
    2.0084   12.8523    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
    2.6215   12.3003    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  1  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
   -1.4289    7.1786    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
   -2.0964    6.6937    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
    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
    3.4061   12.5552    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
    5.2454   10.8991    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
    4.0192   12.0032    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
   -3.4824    6.0815    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
    1.2342    7.2259    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
    2.7424    8.9009    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
   -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
    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
    4.6323   11.4512    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
    3.6762   10.3893    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
   -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
  3  2  2  0  0  0  0
  6  1  1  4  0  0  0
  7  4  1  1  0  0  0
  8  5  1  1  0  0  0
  9  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 18  6  2  0  0  0  0
 10 18  1  1  0  0  0
 19  9  2  0  0  0  0
 19 17  1  0  0  0  0
 20  3  1  0  0  0  0
 15 20  1  1  0  0  0
 20 17  1  0  0  0  0
 21  4  1  0  0  0  0
 22  6  1  0  0  0  0
 23  9  1  0  0  0  0
 11 24  1  6  0  0  0
 12 25  1  6  0  0  0
 13 26  1  6  0  0  0
 14 27  1  6  0  0  0
 28 17  2  0  0  0  0
 33  5  1  0  0  0  0
 34  8  1  0  0  0  0
 34 15  1  0  0  0  0
 35  7  1  0  0  0  0
 35 16  1  0  0  0  0
 16 36  1  6  0  0  0
 38 29  1  0  0  0  0
 38 30  2  0  0  0  0
 38 33  1  0  0  0  0
 38 37  1  0  0  0  0
 39 31  1  0  0  0  0
 39 32  2  0  0  0  0
 39 36  1  0  0  0  0
 39 37  1  0  0  0  0
  7 40  1  6  0  0  0
  8 41  1  6  0  0  0
 10 42  1  6  0  0  0
 11 43  1  1  0  0  0
 12 44  1  1  0  0  0
 13 45  1  6  0  0  0
 14 46  1  1  0  0  0
 15 47  1  6  0  0  0
 16 48  1  1  0  0  0
M  CHG  2  22  -1  23  -1
M  END
> <DATABASE_ID>
MMDBc0056357

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/p-2/t7-,8-,10+,11-,12-,13-,14-,15-,16-/m1/s1

> <INCHI_KEY>
LFTYTUAZOPRMMI-ZYQOOJPVSA-L

> <FORMULA>
C17H25N3O17P2

> <MOLECULAR_WEIGHT>
605.34

> <EXACT_MASS>
605.067017513

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.01218663682006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3S,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)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate

> <JCHEM_LOGP>
-4.097538341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.176021894281293

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7345751858931884

> <JCHEM_PKA_STRONGEST_BASIC>
-3.627911848257394

> <JCHEM_POLAR_SURFACE_AREA>
313.05000000000007

> <JCHEM_REFRACTIVITY>
139.50109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3S,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]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate

> <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       3.749  23.991   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.621   7.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.716   8.377   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.151  17.332   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.043  12.971   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.894  22.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.007  18.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.421  12.495   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.153   7.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.718  20.424   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.327  19.869   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  13.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.182  20.900   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.913  12.495   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.437  11.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.398  18.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.874   9.945   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.573  21.454   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -6.779   8.699   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -4.343   9.784   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       8.831  15.826   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.358  23.436   0.000  0.00  0.00           O-1
HETATM   23  O   UNK     0      -7.058   6.047   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0       9.791  20.345   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667  14.940   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.503  22.406   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.378  12.971   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.500  11.352   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.352  16.418   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.304  13.488   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.106  17.255   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.119  16.615   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.363  14.477   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.897  11.030   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.542  17.887   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.933  18.442   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       3.293  15.429   0.000  0.00  0.00           O+0
HETATM   38  P   UNK     0       1.828  14.953   0.000  0.00  0.00           P+0
HETATM   39  P   UNK     0       3.613  16.935   0.000  0.00  0.00           P+0
HETATM   40  H   UNK     0       9.471  18.839   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.181  14.016   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.038  21.930   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       8.647  21.376   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.040  14.099   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.862  19.393   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.002  11.406   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.738   9.658   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.253  19.948   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    3    9                                                       
CONECT    3    2   20                                                       
CONECT    4    7   21                                                       
CONECT    5    8   33                                                       
CONECT    6    1   18   22                                                  
CONECT    7    4   11   35   40                                             
CONECT    8    5   12   34   41                                             
CONECT    9    2   19   23                                                  
CONECT   10   13   16   18   42                                             
CONECT   11    7   13   24   43                                             
CONECT   12    8   14   25   44                                             
CONECT   13   10   11   26   45                                             
CONECT   14   12   15   27   46                                             
CONECT   15   14   20   34   47                                             
CONECT   16   10   35   36   48                                             
CONECT   17   19   20   28                                                  
CONECT   18    6   10                                                       
CONECT   19    9   17                                                       
CONECT   20    3   15   17                                                  
CONECT   21    4                                                            
CONECT   22    6                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   17                                                            
CONECT   29   38                                                            
CONECT   30   38                                                            
CONECT   31   39                                                            
CONECT   32   39                                                            
CONECT   33    5   38                                                       
CONECT   34    8   15                                                       
CONECT   35    7   16                                                       
CONECT   36   16   39                                                       
CONECT   37   38   39                                                       
CONECT   38   29   30   33   37                                             
CONECT   39   31   32   36   37                                             
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  100    0
END

Synonyms

Value	Source
UDP-N-Acetyl-alpha-D-mannosamine	ChEBI
UDP-N-Acetyl-a-D-mannosamine	Generator
UDP-N-Acetyl-α-D-mannosamine	Generator
UDP-N-Acetyl-a-D-mannosamine(2-)	Generator
UDP-N-Acetyl-α-D-mannosamine(2-)	Generator
Uridine diphosphate N-acetylmannosamine	MeSH
UDP-ManNAc	MeSH

Molecular Formula

C₁₇H₂₅N₃O₁₇P₂

Average Mass

605.34

Monoisotopic Mass

605.067017513

IUPAC Name

N-[(2R,3S,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)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate

Traditional Name

N-[(2R,3S,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]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidate

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]2([H])N=C(C)[O-])O[C@@]([H])(N2C=CC([O-])=NC2=O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/p-2/t7-,8-,10+,11-,12-,13-,14-,15-,16-/m1/s1

InChI Key

LFTYTUAZOPRMMI-ZYQOOJPVSA-L

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

UDP-N-acetyl-D-mannosamine(2-) (CHEBI:68623 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-4.1	ChemAxon
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	313.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	139.5 m³·mol⁻¹	ChemAxon
Polarizability	50.01 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

Not Available

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0013490	N-acetyl-alpha-D-glucosaminyl-di-trans,octa-cis-undecaprenyl diphosphate	Hydrogen Ion	N-acetylglucosaminyldiphosphoundecaprenol N-acetyl-beta-D-mannosaminyltransferase	Conversion of GlcNAc-PP-undecaprenol into ManNAc-GlcNAc-PP-undecaprenol	RHEA	34755880
MMDBr0013630	Uridine diphosphate-N-acetylglucosamine	UDP-N-acetyl-alpha-D-mannosamine	Probable UDP-N-acetylglucosamine 2-epimerase	Epimerization	RHEA	34755880
MMDBr0014578	Water	Hydrogen Ion	UDP-N-acetyl-D-mannosamine dehydrogenase	Dehydrogenation	RHEA	34755880

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	Firmicutes	11	Human feces; Human ; Human subgingival plaque; Human saliva
Bacteria	Proteobacteria	10	Human mucosa; Human ; Human feces
Archaea/Archaea	Euryarchaeota	7
Bacteria	Thermotogae	1

Exposure Sources

Source Type	Source Sub-type	Species	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28533242

KEGG Compound ID

Not Available

BioCyc ID

UDP-MANNAC

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245190

PDB ID

Not Available

ChEBI ID

68623

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-mannosamine (MMDBc0056357)

MOL for #<Metabolite:0x00007fe2d5e07f08>

3D MOL for #<Metabolite:0x00007fe2d5e07f08>

3D SDF for #<Metabolite:0x00007fe2d5e07f08>

3D-SDF for #<Metabolite:0x00007fe2d5e07f08>

PDB for #<Metabolite:0x00007fe2d5e07f08>

3D PDB for #<Metabolite:0x00007fe2d5e07f08>

SMILES for #<Metabolite:0x00007fe2d5e07f08>

INCHI for #<Metabolite:0x00007fe2d5e07f08>

Structure for #<Metabolite:0x00007fe2d5e07f08>

3D Structure for #<Metabolite:0x00007fe2d5e07f08>