MiMeDB: Showing metabocard for dTDP-thomosamine (MMDBc0032177)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:05:39 UTC

Update Date

2022-08-31 18:31:20 UTC

Metabolite ID

MMDBc0032177

Metabolite Identification

Common Name

dTDP-thomosamine

Description

dTDP-thomosamine is an intermediate in dTDP-N-acetylthomosamine biosynthesis in E.coli. It is a substrate for the enzyme dTDP-fucosamine acetyltransferase which catalyzes the reaction dTDP-thomosamine + acetyl-CoA -> dTDP-N-acetylthomosamine + coenzyme A + H+. It is also a product for enzyme dTDP-4-dehydro-6-deoxy-D-glucose transaminase which catalyzes reaction dTDP-4-dehydro-6-deoxy-Œ±-D-glucopyranose + L-glutamate -> dTDP-thomosamine + 2-oxoglutarate (BioCyc compound: TDP-D-FUCOSAMINE).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533006301518552D          

 43 45  0  0  0  0            999 V2000
    2.8723   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870    4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -3.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078   -3.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155    3.6612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1610   -0.3564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4936   -0.8413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5735   -1.6259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7286    3.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5571    2.3022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7725    2.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0283   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594    2.5993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8789   -2.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    3.3641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3639   -2.8746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585   -2.2934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610    0.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1702    1.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5132   -4.2957    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.2145   -1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020   -0.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078    1.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    1.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    0.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309    3.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485   -1.6259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    0.4754    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    1.5374    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    3.9161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    0.0181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -1.4247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990   -2.3610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417    2.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    2.8542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3856    1.4952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878    1.7923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  1  0  0  0
  8  3  1  0  0  0  0
  9  5  1  6  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  1  0  0  0  0
 11 17  1  1  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  4  1  0  0  0  0
 10 19  1  6  0  0  0
 19 16  1  0  0  0  0
  8 20  1  1  0  0  0
 12 21  1  6  0  0  0
 13 22  1  6  0  0  0
 23 14  1  0  0  0  0
 24 16  2  0  0  0  0
 29  5  1  0  0  0  0
 30  7  1  0  0  0  0
 30 15  1  0  0  0  0
 31  9  1  0  0  0  0
 31 10  1  0  0  0  0
 15 32  1  6  0  0  0
 34 25  1  0  0  0  0
 34 26  2  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 27  1  0  0  0  0
 35 28  2  0  0  0  0
 35 32  1  0  0  0  0
 35 33  1  0  0  0  0
  7 36  1  6  0  0  0
  8 37  1  6  0  0  0
  9 38  1  1  0  0  0
 10 39  1  1  0  0  0
 11 40  1  6  0  0  0
 12 41  1  6  0  0  0
 13 42  1  1  0  0  0
 15 43  1  1  0  0  0
M  CHG  1  23  -1
M  END


  Mrv1533006301518552D          

 43 45  0  0  0  0            999 V2000
    2.8723   -4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870    4.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8285   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7229   -3.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078   -3.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1155    3.6612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1610   -0.3564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4936   -0.8413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5735   -1.6259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7286    3.1091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5571    2.3022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7725    2.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0283   -3.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594    2.5993    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8789   -2.2071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132    3.3641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3639   -2.8746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585   -2.2934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610    0.4685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1702    1.7501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009    1.2403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5132   -4.2957    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.2145   -1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5020   -0.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0078    1.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0102    1.3658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962    1.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5375    0.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3309    3.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485   -1.6259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.7304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    0.4754    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2032    1.5374    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9001    3.9161    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    0.0181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -1.4247    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990   -2.3610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417    2.5571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9440    2.8542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3856    1.4952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878    1.7923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  1  1  0  0  0
  8  3  1  0  0  0  0
  9  5  1  6  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  1  0  0  0  0
 11 17  1  1  0  0  0
 18 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  4  1  0  0  0  0
 10 19  1  6  0  0  0
 19 16  1  0  0  0  0
  8 20  1  1  0  0  0
 12 21  1  6  0  0  0
 13 22  1  6  0  0  0
 23 14  1  0  0  0  0
 24 16  2  0  0  0  0
 29  5  1  0  0  0  0
 30  7  1  0  0  0  0
 30 15  1  0  0  0  0
 31  9  1  0  0  0  0
 31 10  1  0  0  0  0
 15 32  1  6  0  0  0
 34 25  1  0  0  0  0
 34 26  2  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35 27  1  0  0  0  0
 35 28  2  0  0  0  0
 35 32  1  0  0  0  0
 35 33  1  0  0  0  0
  7 36  1  6  0  0  0
  8 37  1  6  0  0  0
  9 38  1  1  0  0  0
 10 39  1  1  0  0  0
 11 40  1  6  0  0  0
 12 41  1  6  0  0  0
 13 42  1  1  0  0  0
 15 43  1  1  0  0  0
M  CHG  1  23  -1
M  END
> <DATABASE_ID>
MMDBc0032177

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C([O-])=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/p-1/t7-,8+,9-,10-,11+,12+,13-,15-/m1/s1

> <INCHI_KEY>
UIVJXHWSIFBBCY-FQLHZTMTSA-M

> <FORMULA>
C16H26N3O14P2

> <MOLECULAR_WEIGHT>
546.339

> <EXACT_MASS>
546.089550105

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.616296330079365

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(2R,4S,5R)-5-[({[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-2-yl]-5-methyl-2-oxo-1,2-dihydropyrimidin-4-olate

> <ALOGPS_LOGP>
-1.68

> <JCHEM_LOGP>
-3.606055006211045

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1763138500059607

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.73259922746869

> <JCHEM_PKA_STRONGEST_BASIC>
8.885409144205257

> <JCHEM_POLAR_SURFACE_AREA>
263.18999999999994

> <JCHEM_REFRACTIVITY>
120.28799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,4S,5R)-5-{[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-2-yl]-5-methyl-2-oxopyrimidin-4-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUN-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-15         0                                  
HETATM    1  C   UNK     0       5.362  -8.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.136   8.341   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.280  -1.570   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.083  -5.688   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.323  -1.095   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.988  -6.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.816   6.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.034  -0.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.788  -1.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.804  -3.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.960   5.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.640   4.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.175   3.821   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.519  -6.773   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.031   4.852   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.241  -4.120   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -8.425   6.280   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       8.146  -5.366   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       5.709  -4.281   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       4.034   0.875   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.784   3.267   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.855   2.315   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.425  -8.019   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0       7.867  -2.713   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.937  -0.577   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.015   2.352   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.752   2.549   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.740   3.190   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.003   0.412   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.351   6.358   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       3.264  -3.035   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.566   4.376   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.926   1.363   0.000  0.00  0.00           O+0
HETATM   34  P   UNK     0      -0.461   0.887   0.000  0.00  0.00           P+0
HETATM   35  P   UNK     0      -2.246   2.870   0.000  0.00  0.00           P+0
HETATM   36  H   UNK     0      -7.280   7.310   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.662   0.034   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.699  -2.659   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.105  -4.407   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      -8.105   4.773   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.495   5.328   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      -6.320   2.791   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.711   3.346   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8   10                                                       
CONECT    4    6   19                                                       
CONECT    5    9   29                                                       
CONECT    6    1    4   14                                                  
CONECT    7    2   11   30   36                                             
CONECT    8    3    9   20   37                                             
CONECT    9    5    8   31   38                                             
CONECT   10    3   19   31   39                                             
CONECT   11    7   12   17   40                                             
CONECT   12   11   13   21   41                                             
CONECT   13   12   15   22   42                                             
CONECT   14    6   18   23                                                  
CONECT   15   13   30   32   43                                             
CONECT   16   18   19   24                                                  
CONECT   17   11                                                            
CONECT   18   14   16                                                       
CONECT   19    4   10   16                                                  
CONECT   20    8                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   16                                                            
CONECT   25   34                                                            
CONECT   26   34                                                            
CONECT   27   35                                                            
CONECT   28   35                                                            
CONECT   29    5   34                                                       
CONECT   30    7   15                                                       
CONECT   31    9   10                                                       
CONECT   32   15   35                                                       
CONECT   33   34   35                                                       
CONECT   34   25   26   29   33                                             
CONECT   35   27   28   32   33                                             
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   15                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

Synonyms

Value	Source
dTDP-4-Amino-4,6-dideoxy-alpha-D-galactose	ChEBI
dTDP-alpha-D-Fucosamine	ChEBI
dTDP-4-Amino-4,6-dideoxy-a-D-galactose	Generator
dTDP-4-Amino-4,6-dideoxy-α-D-galactose	Generator
dTDP-a-D-Fucosamine	Generator
dTDP-Α-D-fucosamine	Generator
dTDP-4-amino-4,6-Dideoxy-a-D-galactose(1-)	Generator
dTDP-4-amino-4,6-Dideoxy-α-D-galactose(1-)	Generator

Molecular Formula

C₁₆H₂₆N₃O₁₄P₂

Average Mass

546.339

Monoisotopic Mass

546.089550105

IUPAC Name

1-[(2R,4S,5R)-5-[({[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-2-yl]-5-methyl-2-oxo-1,2-dihydropyrimidin-4-olate

Traditional Name

1-[(2R,4S,5R)-5-{[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-2-yl]-5-methyl-2-oxopyrimidin-4-olate

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[C@]([H])(O)[C@@]1([H])O)N1C=C(C)C([O-])=NC1=O

InChI Identifier

InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/p-1/t7-,8+,9-,10-,11+,12+,13-,15-/m1/s1

InChI Key

UIVJXHWSIFBBCY-FQLHZTMTSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenyl phospho carbohydrates

Alternative Parents

Substituents

Polyterpenoid
Polyprenyl phospho carbohydrate
Bactoprenol diphosphate
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
N-acyl-alpha-hexosamine
Hexose monosaccharide
Isoprenoid phosphate
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

polyprenyl glycosyl phosphate (CHEBI:16511 )
N-acyl-D-glucosamine 1-phosphate (CHEBI:16511 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	22.5 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	8.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	263.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	120.29 m³·mol⁻¹	ChemAxon
Polarizability	45.62 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	splash10-0002-1400190000-629ccbef77969751ebb9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0097-0381090000-37ff850190468cd49757	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-47b5012caf79b84af2b6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000m-9000040000-4032275cb4d3aee7308f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9100010000-1233f33c129da68c6986	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-9100000000-be192b48c764816a4ce5	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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	Microbial Links
Bacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

TDP-D-FUCOSAMINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678920

PDB ID

Not Available

ChEBI ID

68492

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 ]
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 dTDP-thomosamine (MMDBc0032177)

MOL for #<Metabolite:0x00007fecec370790>

3D MOL for #<Metabolite:0x00007fecec370790>

3D SDF for #<Metabolite:0x00007fecec370790>

3D-SDF for #<Metabolite:0x00007fecec370790>

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Structure for #<Metabolite:0x00007fecec370790>

3D Structure for #<Metabolite:0x00007fecec370790>