Showing metabocard for ADP-Mannose (MMDBc0048913)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 22:14:46 UTC
Update Date2024-04-30 20:37:42 UTC
Metabolite IDMMDBc0048913
Metabolite Identification
Common NameADP-Mannose
DescriptionADP-mannose is one of the major substrates of human hydrolases. Nudix hydrolases catalyze the hydrolysis of a variety of nucleoside diphosphate derivatives, and ADP-sugar pyrophosphatase are non-specific nucleoside diphosphosugar or diphosphoalcohol (NDP-X) pyrophosphatases, which hydrolyse some nonreducing NDP-X substrates. It has been found in erythrocytes, placenta and liver. (PMID: 1128712 , 10722730 , 9693963 ).
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fa4bc211890>


  Mrv1652304302200142D          

 61 64  0  0  1  0            999 V2000
   -5.9078   -7.5942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1541   -7.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4867   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1955   -6.6730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9320   -6.7504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -7.7804    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4004   -8.2654    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656   -7.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -7.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5582   -7.9666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -7.1462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -6.3257    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -6.2394    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.5512   -6.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -5.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -5.0203    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6344   -4.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 15 16  1  0  0  0  0
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 23 24  1  6  0  0  0
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 26 27  1  6  0  0  0
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  9 50  1  0  0  0  0
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  6 58  1  0  0  0  0
 58 59  1  1  0  0  0
 58 60  1  1  0  0  0
 60 61  1  0  0  0  0
M  CHG  2  13  -1  17  -1
M  END
Download

3D MOL for #<Metabolite:0x00007fa4bc211890>

Download
3D SDF for #<Metabolite:0x00007fa4bc211890>

  Mrv1652304302200142D          

 61 64  0  0  1  0            999 V2000
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   -4.4867   -7.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  13  -1  17  -1
M  END
> <DATABASE_ID>
MMDBc0048913

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/p-2/t5-,6-,8-,9-,10+,11-,12+,15-,16-/m1/s1

> <INCHI_KEY>
WFPZSXYXPSUOPY-RYRBFGMPSA-L

> <FORMULA>
C16H23N5O15P2

> <MOLECULAR_WEIGHT>
587.329

> <EXACT_MASS>
587.067686216

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.088570893728445

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphono]oxy}phosphonate

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-6.7725679530330645

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.107282857130621

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7298676687415737

> <JCHEM_PKA_STRONGEST_BASIC>
3.99312463028185

> <JCHEM_POLAR_SURFACE_AREA>
317.41

> <JCHEM_REFRACTIVITY>
114.84240000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphono]oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fa4bc211890>
Download
PDB for #<Metabolite:0x00007fa4bc211890>
HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  H   UNK     0     -11.028 -14.176   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      -9.621 -14.802   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.375 -13.897   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -7.832 -12.456   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0      -9.206 -12.601   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0      -6.968 -14.523   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      -8.214 -15.429   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0      -5.722 -13.618   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.316 -14.245   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -2.909 -14.871   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0      -3.070 -13.339   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0      -3.231 -11.808   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0      -1.699 -11.647   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      -4.762 -11.969   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.392 -10.276   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0      -2.146  -9.371   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      -1.241 -10.617   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -3.051  -8.125   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.900  -8.466   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.061  -6.934   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -2.037  -5.743   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.599  -7.006   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       0.185  -6.029   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       0.426  -7.550   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       0.185  -4.489   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       3.171  -3.772   0.000  0.00  0.00           H+0
HETATM   28  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.320  -1.303   0.000  0.00  0.00           H+0
HETATM   31  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       6.258  -0.533   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       7.591  -2.843   0.000  0.00  0.00           H+0
HETATM   37  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0       4.924   1.777   0.000  0.00  0.00           N+0
HETATM   40  H   UNK     0       6.258   2.547   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.590   2.547   0.000  0.00  0.00           H+0
HETATM   42  C   UNK     0       2.555  -5.259   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0       3.254  -6.631   0.000  0.00  0.00           H+0
HETATM   44  O   UNK     0       4.095  -5.259   0.000  0.00  0.00           O+0
HETATM   45  H   UNK     0       5.635  -5.254   0.000  0.00  0.00           H+0
HETATM   46  C   UNK     0       1.650  -6.505   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0       1.174  -5.040   0.000  0.00  0.00           H+0
HETATM   48  O   UNK     0       2.126  -7.970   0.000  0.00  0.00           O+0
HETATM   49  H   UNK     0       2.601  -9.434   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0      -4.155 -15.776   0.000  0.00  0.00           C+0
HETATM   51  H   UNK     0      -3.994 -17.308   0.000  0.00  0.00           H+0
HETATM   52  O   UNK     0      -2.748 -16.403   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0      -1.341 -17.029   0.000  0.00  0.00           H+0
HETATM   54  C   UNK     0      -5.400 -16.681   0.000  0.00  0.00           C+0
HETATM   55  H   UNK     0      -6.646 -17.587   0.000  0.00  0.00           H+0
HETATM   56  O   UNK     0      -5.239 -18.213   0.000  0.00  0.00           O+0
HETATM   57  H   UNK     0      -5.078 -19.745   0.000  0.00  0.00           H+0
HETATM   58  C   UNK     0      -6.807 -16.055   0.000  0.00  0.00           C+0
HETATM   59  H   UNK     0      -5.561 -15.150   0.000  0.00  0.00           H+0
HETATM   60  O   UNK     0      -8.053 -16.960   0.000  0.00  0.00           O+0
HETATM   61  H   UNK     0      -9.299 -17.865   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7    8   58                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   50                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25   46                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28   42                                             
CONECT   27   26                                                            
CONECT   28   26   29   38                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   28   32                                                  
CONECT   39   33   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   26   43   44   46                                             
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46   42   23   47   48                                             
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50    9   51   52   54                                             
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52                                                            
CONECT   54   50   55   56   58                                             
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56                                                            
CONECT   58   54    6   59   60                                             
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

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3D PDB for #<Metabolite:0x00007fa4bc211890>
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SMILES for #<Metabolite:0x00007fa4bc211890>
[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=NC4=C(N=C([H])N=C34)N([H])[H])[C@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Download
INCHI for #<Metabolite:0x00007fa4bc211890>
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/p-2/t5-,6-,8-,9-,10+,11-,12+,15-,16-/m1/s1
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Synonyms
ValueSource
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonic acidGenerator
Molecular FormulaC16H23N5O15P2
Average Mass587.329
Monoisotopic Mass587.067686216
IUPAC Name[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphono]oxy}phosphonate
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphono]oxyphosphonate
CAS Registry Number28447-34-9
SMILES
[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP([O-])(=O)OP([O-])(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=NC4=C(N=C([H])N=C34)N([H])[H])[C@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
InChI Identifier
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/p-2/t5-,6-,8-,9-,10+,11-,12+,15-,16-/m1/s1
InChI KeyWFPZSXYXPSUOPY-RYRBFGMPSA-L