MiMeDB: Showing metabocard for GDP-N,N'-diacetylbacillosamine (MMDBc0056012)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:13:15 UTC

Update Date

2022-08-12 20:09:32 UTC

Metabolite ID

MMDBc0056012

Metabolite Identification

Common Name

GDP-N,N'-diacetylbacillosamine

Description

GDP-N,N'-diacetylbacillosamine(2-) belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-N,N'-diacetylbacillosamine(2-) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on GDP-N,N'-diacetylbacillosamine(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222132D          

 53 56  0  0  1  0            999 V2000
   -5.7689   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175   -9.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -8.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152   -7.7804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3501   -8.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -8.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9290   -8.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5079   -8.4516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1753   -8.9365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5941   -7.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964   -9.0858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542   -8.7871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363   -7.9298    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1730   -7.4817    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -9.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468   -5.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -6.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -6.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -7.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267   -7.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -6.3257    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -8.2654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0540   -4.0448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -9.4214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -9.2720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -3.6139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -8.1160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -1.5666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8404   -7.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  7  2  1  4  0  0  0
  8  3  1  4  0  0  0
  9  4  1  1  0  0  0
 10  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 21 20  2  0  0  0  0
 22  5  2  0  0  0  0
 22 12  1  0  0  0  0
 23  7  2  0  0  0  0
 10 23  1  6  0  0  0
 24  8  2  0  0  0  0
 11 24  1  6  0  0  0
 25 16  1  0  0  0  0
 25 20  1  0  0  0  0
 26 17  2  0  0  0  0
 26 20  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 18 27  1  1  0  0  0
 28  7  1  0  0  0  0
 29  8  1  0  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 33 17  1  0  0  0  0
 38  4  1  0  0  0  0
 39  6  1  0  0  0  0
 39 19  1  0  0  0  0
 40  9  1  0  0  0  0
 40 18  1  0  0  0  0
 19 41  1  6  0  0  0
 43 34  1  0  0  0  0
 43 35  2  0  0  0  0
 43 38  1  0  0  0  0
 43 42  1  0  0  0  0
 44 36  1  0  0  0  0
 44 37  2  0  0  0  0
 44 41  1  0  0  0  0
 44 42  1  0  0  0  0
  6 45  1  6  0  0  0
  9 46  1  6  0  0  0
 10 47  1  1  0  0  0
 11 48  1  1  0  0  0
 13 49  1  1  0  0  0
 14 50  1  6  0  0  0
 15 51  1  1  0  0  0
 18 52  1  6  0  0  0
 19 53  1  1  0  0  0
M  CHG  2  28  -1  29  -1
M  END


  Mrv1652306172222132D          

 53 56  0  0  1  0            999 V2000
   -5.7689   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175   -9.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -8.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0152   -7.7804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3501   -8.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868   -8.3022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9290   -8.6009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5079   -8.4516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1753   -8.9365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5941   -7.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5964   -9.0858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7542   -8.7871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4363   -7.9298    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1730   -7.4817    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0891   -9.7570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468   -5.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1924   -6.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8334   -6.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -7.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267   -7.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -6.3257    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6827   -8.2654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0540   -4.0448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8428   -9.4214    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4216   -9.2720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -3.6139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2616   -8.1160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -1.5666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8404   -7.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  7  2  1  4  0  0  0
  8  3  1  4  0  0  0
  9  4  1  1  0  0  0
 10  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 17 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 21 20  2  0  0  0  0
 22  5  2  0  0  0  0
 22 12  1  0  0  0  0
 23  7  2  0  0  0  0
 10 23  1  6  0  0  0
 24  8  2  0  0  0  0
 11 24  1  6  0  0  0
 25 16  1  0  0  0  0
 25 20  1  0  0  0  0
 26 17  2  0  0  0  0
 26 20  1  0  0  0  0
 27  5  1  0  0  0  0
 27 16  1  0  0  0  0
 18 27  1  1  0  0  0
 28  7  1  0  0  0  0
 29  8  1  0  0  0  0
 13 30  1  6  0  0  0
 14 31  1  6  0  0  0
 15 32  1  6  0  0  0
 33 17  1  0  0  0  0
 38  4  1  0  0  0  0
 39  6  1  0  0  0  0
 39 19  1  0  0  0  0
 40  9  1  0  0  0  0
 40 18  1  0  0  0  0
 19 41  1  6  0  0  0
 43 34  1  0  0  0  0
 43 35  2  0  0  0  0
 43 38  1  0  0  0  0
 43 42  1  0  0  0  0
 44 36  1  0  0  0  0
 44 37  2  0  0  0  0
 44 41  1  0  0  0  0
 44 42  1  0  0  0  0
  6 45  1  6  0  0  0
  9 46  1  6  0  0  0
 10 47  1  1  0  0  0
 11 48  1  1  0  0  0
 13 49  1  1  0  0  0
 14 50  1  6  0  0  0
 15 51  1  1  0  0  0
 18 52  1  6  0  0  0
 19 53  1  1  0  0  0
M  CHG  2  28  -1  29  -1
M  END
> <DATABASE_ID>
MMDBc0056012

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(C)[C@@]([H])(N=C(C)[O-])[C@]([H])(O)[C@@]2([H])N=C(C)[O-])O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C20H31N7O15P2/c1-6-10(23-7(2)28)14(31)11(24-8(3)29)19(39-6)41-44(36,37)42-43(34,35)38-4-9-13(30)15(32)18(40-9)27-5-22-12-16(27)25-20(21)26-17(12)33/h5-6,9-11,13-15,18-19,30-32H,4H2,1-3H3,(H,23,28)(H,24,29)(H,34,35)(H,36,37)(H3,21,25,26,33)/p-2/t6-,9-,10-,11-,13-,14+,15-,18-,19-/m1/s1

> <INCHI_KEY>
UFDVBOLRIAJRHF-ZSSIDFSASA-L

> <FORMULA>
C20H29N7O15P2

> <MOLECULAR_WEIGHT>
669.435

> <EXACT_MASS>
669.120784418

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
57.99060711652248

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2R,3R,4S,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4-hydroxy-6-methyl-5-[(1-oxidoethylidene)amino]oxan-3-yl]ethanecarboximidate

> <JCHEM_LOGP>
-3.3592440794442697

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2361389886968537

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5738638066158455

> <JCHEM_PKA_STRONGEST_BASIC>
2.344108503037516

> <JCHEM_POLAR_SURFACE_AREA>
338.57000000000005

> <JCHEM_REFRACTIVITY>
171.89530000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2R,3R,4S,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-4-hydroxy-6-methyl-5-[(1-oxidoethylidene)amino]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     -10.769 -13.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.099 -17.239   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.488 -16.124   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.454  -6.934   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.362 -14.523   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.854 -16.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.895 -15.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.208  -6.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.201 -16.055   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.548 -15.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.744  -6.505   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.794 -16.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.161  -5.259   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.709 -14.245   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.198  -2.843   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0     -10.447 -16.960   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      -5.141 -16.403   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   28  O   UNK     0     -12.015 -14.802   0.000  0.00  0.00           O-1
HETATM   29  O   UNK     0      -4.056 -13.966   0.000  0.00  0.00           O-1
HETATM   30  O   UNK     0      -0.268  -7.970   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -7.633 -18.213   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.701  -5.259   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.634 -10.617   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.444  -8.125   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -4.093 -11.647   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -7.156 -11.969   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -3.293  -8.466   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -8.116 -13.618   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.208  -4.489   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.463 -13.339   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -5.785 -10.276   0.000  0.00  0.00           O+0
HETATM   43  P   UNK     0      -4.539  -9.371   0.000  0.00  0.00           P+0
HETATM   44  P   UNK     0      -5.624 -11.808   0.000  0.00  0.00           P+0
HETATM   45  H   UNK     0     -10.608 -15.429   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.967  -7.550   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      -9.040 -17.587   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.387 -17.308   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.777  -6.746   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0      -7.955 -15.150   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.861  -3.887   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.833  -2.924   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.302 -14.871   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    9   38                                                       
CONECT    5   22   27                                                       
CONECT    6    1   10   39   45                                             
CONECT    7    2   23   28                                                  
CONECT    8    3   24   29                                                  
CONECT    9    4   13   40   46                                             
CONECT   10    6   14   23   47                                             
CONECT   11   14   19   24   48                                             
CONECT   12   16   17   22                                                  
CONECT   13    9   15   30   49                                             
CONECT   14   10   11   31   50                                             
CONECT   15   13   18   32   51                                             
CONECT   16   12   25   27                                                  
CONECT   17   12   26   33                                                  
CONECT   18   15   27   40   52                                             
CONECT   19   11   39   41   53                                             
CONECT   20   21   25   26                                                  
CONECT   21   20                                                            
CONECT   22    5   12                                                       
CONECT   23    7   10                                                       
CONECT   24    8   11                                                       
CONECT   25   16   20                                                       
CONECT   26   17   20                                                       
CONECT   27    5   16   18                                                  
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   17                                                            
CONECT   34   43                                                            
CONECT   35   43                                                            
CONECT   36   44                                                            
CONECT   37   44                                                            
CONECT   38    4   43                                                       
CONECT   39    6   19                                                       
CONECT   40    9   18                                                       
CONECT   41   19   44                                                       
CONECT   42   43   44                                                       
CONECT   43   34   35   38   42                                             
CONECT   44   36   37   41   42                                             
CONECT   45    6                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   11                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

Synonyms

Value	Source
GDP-2,4-Diacetamido-2,4,6-trideoxy-alpha-D-glucopyranose(2-)	ChEBI
GDP-N,N'-diacetylbacillosamine	ChEBI
GDP-2,4-Diacetamido-2,4,6-trideoxy-a-D-glucopyranose(2-)	Generator
GDP-2,4-Diacetamido-2,4,6-trideoxy-α-D-glucopyranose(2-)	Generator

Molecular Formula

C₂₀H₂₉N₇O₁₅P₂

Average Mass

669.435

Monoisotopic Mass

669.120784418

IUPAC Name

N-[(2R,3R,4S,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4-hydroxy-6-methyl-5-[(1-oxidoethylidene)amino]oxan-3-yl]ethanecarboximidate

Traditional Name

N-[(2R,3R,4S,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-4-hydroxy-6-methyl-5-[(1-oxidoethylidene)amino]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])(C)[C@@]([H])(N=C(C)[O-])[C@]([H])(O)[C@@]2([H])N=C(C)[O-])O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C20H31N7O15P2/c1-6-10(23-7(2)28)14(31)11(24-8(3)29)19(39-6)41-44(36,37)42-43(34,35)38-4-9-13(30)15(32)18(40-9)27-5-22-12-16(27)25-20(21)26-17(12)33/h5-6,9-11,13-15,18-19,30-32H,4H2,1-3H3,(H,23,28)(H,24,29)(H,34,35)(H,36,37)(H3,21,25,26,33)/p-2/t6-,9-,10-,11-,13-,14+,15-,18-,19-/m1/s1

InChI Key

UFDVBOLRIAJRHF-ZSSIDFSASA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Pyrimidone
Aminopyrimidine
Organic phosphoric acid derivative
Oxane
N-substituted imidazole
Monosaccharide
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Azole
Acetamide
Imidazole
Tetrahydrofuran
Vinylogous amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid or derivatives
Azacycle
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organonitrogen compound
Organic oxide
Alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Carbonyl group
Amine
Organopnictogen compound
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nucleotide-sugar oxoanion (CHEBI:86016 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.4	ChemAxon
pKa (Strongest Acidic)	1.57	ChemAxon
pKa (Strongest Basic)	2.34	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	338.57 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	171.9 m³·mol⁻¹	ChemAxon
Polarizability	57.99 Å³	ChemAxon
Number of Rings	4	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

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	1	Human ; Human feces

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

58145461

KEGG Compound ID

Not Available

BioCyc ID

CPD-13164

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52940139

PDB ID

Not Available

ChEBI ID

86016

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 GDP-N,N'-diacetylbacillosamine (MMDBc0056012)

MOL for #<Metabolite:0x00007fecaf45a990>

3D MOL for #<Metabolite:0x00007fecaf45a990>

3D SDF for #<Metabolite:0x00007fecaf45a990>

3D-SDF for #<Metabolite:0x00007fecaf45a990>

PDB for #<Metabolite:0x00007fecaf45a990>

3D PDB for #<Metabolite:0x00007fecaf45a990>

SMILES for #<Metabolite:0x00007fecaf45a990>

INCHI for #<Metabolite:0x00007fecaf45a990>

Structure for #<Metabolite:0x00007fecaf45a990>

3D Structure for #<Metabolite:0x00007fecaf45a990>