MiMeDB: Showing metabocard for ADP-D-Glycero-D-manno-heptose (MMDBc0030035)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:51:28 UTC

Update Date

2022-08-31 17:38:54 UTC

Metabolite ID

MMDBc0030035

Metabolite Identification

Common Name

ADP-D-Glycero-D-manno-heptose

Description

ADP-D-glycero-D-manno-heptose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. ADP-L-glycero-D-manno-heptose is the lipopolysaccharide core precursor.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10231212422D          

 50 53  0  0  0  0            999 V2000
   -3.4743   -8.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -7.5361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7330   -5.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6468   -6.3800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0656   -5.0746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8931   -6.7156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -8.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -7.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4867   -5.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3142   -6.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -4.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298   -7.4785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943   -6.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698   -6.3225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8192   -4.7391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861   -6.9430    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -4.5897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  1  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  6  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 15  7  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  3  2  0  0  0  0
 19 14  1  0  0  0  0
 20  3  1  0  0  0  0
 20 15  2  0  0  0  0
 21  4  2  0  0  0  0
 21  7  1  0  0  0  0
 22  4  1  0  0  0  0
 22 15  1  0  0  0  0
 16 22  1  1  0  0  0
 23  1  1  0  0  0  0
  5 24  1  1  0  0  0
  8 25  1  6  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
 12 29  1  6  0  0  0
 34  2  1  0  0  0  0
 35  6  1  0  0  0  0
 35 16  1  0  0  0  0
 36 13  1  0  0  0  0
 36 17  1  0  0  0  0
 37 17  1  0  0  0  0
 39 30  1  0  0  0  0
 39 31  2  0  0  0  0
 39 34  1  0  0  0  0
 39 38  1  0  0  0  0
 40 32  1  0  0  0  0
 40 33  2  0  0  0  0
 40 37  1  0  0  0  0
 40 38  1  0  0  0  0
  5 41  1  1  0  0  0
  6 42  1  6  0  0  0
  8 43  1  1  0  0  0
  9 44  1  1  0  0  0
 10 45  1  6  0  0  0
 11 46  1  1  0  0  0
 12 47  1  1  0  0  0
 13 48  1  1  0  0  0
 16 49  1  6  0  0  0
 50 17  1  0  0  0  0
M  END


  Mrv0541 10231212422D          

 50 53  0  0  0  0            999 V2000
   -3.4743   -8.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -7.5361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7330   -5.5596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6468   -6.3800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0656   -5.0746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8931   -6.7156    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3881   -8.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -7.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4867   -5.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3142   -6.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1518   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -4.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6298   -7.4785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -1.7306    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -2.0117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943   -6.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4698   -6.3225    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8192   -4.7391    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6861   -6.9430    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3981   -4.5897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  1  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  6  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 15  7  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  3  2  0  0  0  0
 19 14  1  0  0  0  0
 20  3  1  0  0  0  0
 20 15  2  0  0  0  0
 21  4  2  0  0  0  0
 21  7  1  0  0  0  0
 22  4  1  0  0  0  0
 22 15  1  0  0  0  0
 16 22  1  1  0  0  0
 23  1  1  0  0  0  0
  5 24  1  1  0  0  0
  8 25  1  6  0  0  0
  9 26  1  6  0  0  0
 10 27  1  1  0  0  0
 11 28  1  6  0  0  0
 12 29  1  6  0  0  0
 34  2  1  0  0  0  0
 35  6  1  0  0  0  0
 35 16  1  0  0  0  0
 36 13  1  0  0  0  0
 36 17  1  0  0  0  0
 37 17  1  0  0  0  0
 39 30  1  0  0  0  0
 39 31  2  0  0  0  0
 39 34  1  0  0  0  0
 39 38  1  0  0  0  0
 40 32  1  0  0  0  0
 40 33  2  0  0  0  0
 40 37  1  0  0  0  0
 40 38  1  0  0  0  0
  5 41  1  1  0  0  0
  6 42  1  6  0  0  0
  8 43  1  1  0  0  0
  9 44  1  1  0  0  0
 10 45  1  6  0  0  0
 11 46  1  1  0  0  0
 12 47  1  1  0  0  0
 13 48  1  1  0  0  0
 16 49  1  6  0  0  0
 50 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030035

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CO)[C@@]1([H])OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N5O16P2/c18-14-7-15(20-3-19-14)22(4-21-7)16-11(28)8(25)6(35-16)2-34-39(30,31)38-40(32,33)37-17-12(29)9(26)10(27)13(36-17)5(24)1-23/h3-6,8-13,16-17,23-29H,1-2H2,(H,30,31)(H,32,33)(H2,18,19,20)/t5-,6-,8-,9+,10+,11-,12+,13-,16-,17?/m1/s1

> <INCHI_KEY>
KMSFWBYFWSKGGR-RQWOTHMISA-N

> <FORMULA>
C17H27N5O16P2

> <MOLECULAR_WEIGHT>
619.3677

> <EXACT_MASS>
619.092802865

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
52.501108062417224

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.81

> <JCHEM_LOGP>
-8.038258147170092

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.6346015412797454

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7329410523547581

> <JCHEM_PKA_STRONGEST_BASIC>
4.995083454548712

> <JCHEM_POLAR_SURFACE_AREA>
331.98

> <JCHEM_REFRACTIVITY>
123.04829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   39  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   40  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   41  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5   23                                                       
CONECT    2    6   34                                                       
CONECT    3   19   20                                                       
CONECT    4   21   22                                                       
CONECT    5    1   13   24   41                                             
CONECT    6    2    8   35   42                                             
CONECT    7   14   15   21                                                  
CONECT    8    6   11   25   43                                             
CONECT    9   10   12   26   44                                             
CONECT   10    9   13   27   45                                             
CONECT   11    8   16   28   46                                             
CONECT   12    9   17   29   47                                             
CONECT   13    5   10   36   48                                             
CONECT   14    7   18   19                                                  
CONECT   15    7   20   22                                                  
CONECT   16   11   22   35   49                                             
CONECT   17   12   36   37   50                                             
CONECT   18   14                                                            
CONECT   19    3   14                                                       
CONECT   20    3   15                                                       
CONECT   21    4    7                                                       
CONECT   22    4   15   16                                                  
CONECT   23    1                                                            
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   11                                                            
CONECT   29   12                                                            
CONECT   30   39                                                            
CONECT   31   39                                                            
CONECT   32   40                                                            
CONECT   33   40                                                            
CONECT   34    2   39                                                       
CONECT   35    6   16                                                       
CONECT   36   13   17                                                       
CONECT   37   17   40                                                       
CONECT   38   39   40                                                       
CONECT   39   30   31   34   38                                             
CONECT   40   32   33   37   38                                             
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₂₇N₅O₁₆P₂

Average Mass

619.3677

Monoisotopic Mass

619.092802865

IUPAC Name

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid

Traditional Name

{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)[C@@]1([H])OC([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C17H27N5O16P2/c18-14-7-15(20-3-19-14)22(4-21-7)16-11(28)8(25)6(35-16)2-34-39(30,31)38-40(32,33)37-17-12(29)9(26)10(27)13(36-17)5(24)1-23/h3-6,8-13,16-17,23-29H,1-2H2,(H,30,31)(H,32,33)(H2,18,19,20)/t5-,6-,8-,9+,10+,11-,12+,13-,16-,17?/m1/s1

InChI Key

KMSFWBYFWSKGGR-RQWOTHMISA-N

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-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Oxacycle
Organic oxide
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Organonitrogen compound
Primary alcohol
Primary amine
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ADP-glycero-D-manno-heptose (CHEBI:16693 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.91 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	331.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	52.5 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_48) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910502000-8c3562506ded6f437c8a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0910000000-2624f0a80c52e6957690	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-bede1fb56b90862d8f7f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0api-4901245000-42682d865153e9fc153e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901000000-baf9b8dcb69cf8da70fe	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0563-3900000000-135806b9f5fcb9949d51	2015-09-15	View Spectrum
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

Feces

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
MMDBr0007252	ADP-D-Glycero-D-manno-heptose	ADP-L-Glycero-D-manno-heptose	Not Available		VMH	30371894
MMDBr0007453	D-Glycero-D-manno-heptose 1-phosphate	ADP-D-Glycero-D-manno-heptose	Not Available		VMH	30371894

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	172	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	26	Pig ; Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	88	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	94	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque; Human stool	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441006

PDB ID

Not Available

ChEBI ID

16693

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 ]

Showing metabocard for ADP-D-Glycero-D-manno-heptose (MMDBc0030035)

MOL for #<Metabolite:0x00007fecb3bac4b0>

3D MOL for #<Metabolite:0x00007fecb3bac4b0>

3D SDF for #<Metabolite:0x00007fecb3bac4b0>

3D-SDF for #<Metabolite:0x00007fecb3bac4b0>

PDB for #<Metabolite:0x00007fecb3bac4b0>

3D PDB for #<Metabolite:0x00007fecb3bac4b0>

SMILES for #<Metabolite:0x00007fecb3bac4b0>

INCHI for #<Metabolite:0x00007fecb3bac4b0>

Structure for #<Metabolite:0x00007fecb3bac4b0>

3D Structure for #<Metabolite:0x00007fecb3bac4b0>