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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (786)transporters (2) Show 788 proteins XML

enzymes (786)transporters (2) Show 788 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:49 UTC

HMDB ID

HMDB0001341

Secondary Accession Numbers

HMDB01341

Metabolite Identification

Common Name

ADP

Description

Adenosine diphosphate (ADP), also known as adenosine pyrophosphate (APP), is an important organic compound in metabolism and is essential to the flow of energy in living cells. ADP consists of three important structural components: a sugar backbone attached to adenine and two phosphate groups bonded to the 5 carbon atom of ribose. The diphosphate group of ADP is attached to the 5’ carbon of the sugar backbone, while the adenine attaches to the 1’ carbon. ADP belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. It is an ester of pyrophosphoric acid with the nucleotide adenine. Adenosine diphosphate is a nucleotide. ADP exists in all living species, ranging from bacteria to humans. In humans, ADP is involved in d4-gdi signaling pathway. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308122017232D          

 27 29  0  0  0  0            999 V2000
 9998.7501 9998.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5401 9998.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0475 9999.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7612 9999.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4749 9999.9095    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.1989 9999.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.064410000.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.889510000.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.9126 9999.9217    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.500110000.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.6263 9999.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.325110000.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6616 9999.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2491 9998.7205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0741 9998.7205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3290 9999.5051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.167810000.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9129 9999.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4650 9998.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2719 9998.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5269 9999.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.974810000.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2805 9999.9136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.194410000.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.387410000.9057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.615710000.6328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9949 9999.5010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 16  1  0  0  0  0
 14  1  1  1  0  0  0
 15  2  1  1  0  0  0
 16  3  1  6  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 24 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 21 23  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 26  1  0  0  0  0
 27 23  1  6  0  0  0
 27 14  1  0  0  0  0
 13 27  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -6.6036    1.9413    0.3163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3797    1.4531   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0177    1.6512   -1.4995 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8701    1.2037   -2.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0243    0.5119   -1.2554 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    0.2718    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5000    0.7405    0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5000    0.3509    1.8397 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -0.3314    2.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6273   -0.3855    0.9801 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -1.0284    0.8445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3141   -0.1137    0.6355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7632   -0.9683    0.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9555   -0.1606   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502    0.7184    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927    1.6607    0.6366 P   0  0  1  0  0  5  0  0  0  0  0  0
    3.1246    3.0833    0.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202    1.7029    1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3262    0.9951   -0.7074 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9932    1.0674   -0.6806 P   0  0  2  0  0  5  0  0  0  0  0  0
    6.5235    1.9969    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089    1.6806   -2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6647   -0.4834   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385   -1.8665   -0.6714 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8073   -3.1425   -0.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -1.9000   -0.3738 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5954   -3.2127   -0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3654    1.2740    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    2.9503    0.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    1.3972   -3.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0721   -0.7813    3.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -1.6167    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9339   -1.5179    1.3518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182   -0.7954   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6452    0.4802   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392    0.7833    2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5026    0.9143   -2.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7330   -0.8883   -1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4669   -1.5108   -1.6760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9457   -3.2931    0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8495   -1.5583   -1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7415   -3.2738    0.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  2  0
 16 18  1  0
 16 19  1  0
 20 19  1  6
 20 21  2  0
 20 22  1  0
 20 23  1  0
 13 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  7  2  1  0
 26 11  1  0
 10  6  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  9 31  1  0
 11 32  1  1
 13 33  1  1
 14 34  1  0
 14 35  1  0
 18 36  1  0
 22 37  1  0
 23 38  1  0
 24 39  1  6
 25 40  1  0
 26 41  1  6
 27 42  1  0
M  END


  Mrv1652308122017232D          

 27 29  0  0  0  0            999 V2000
 9998.7501 9998.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5401 9998.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0475 9999.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7612 9999.4959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4749 9999.9095    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.1989 9999.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.064410000.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.889510000.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.9126 9999.9217    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10003.500110000.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.6263 9999.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.325110000.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6616 9999.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2491 9998.7205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0741 9998.7205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3290 9999.5051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.167810000.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9129 9999.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4650 9998.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2719 9998.7935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5269 9999.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.974810000.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2805 9999.9136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.194410000.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.387410000.9057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.615710000.6328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9949 9999.5010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 16  1  0  0  0  0
 14  1  1  1  0  0  0
 15  2  1  1  0  0  0
 16  3  1  6  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
 24 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 21 23  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 26  1  0  0  0  0
 27 23  1  6  0  0  0
 27 14  1  0  0  0  0
 13 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001341

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
XTWYTFMLZFPYCI-KQYNXXCUSA-N

> <FORMULA>
C10H15N5O10P2

> <MOLECULAR_WEIGHT>
427.2011

> <EXACT_MASS>
427.029414749

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.23829042406093

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <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]phosphonic acid

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-4.711847208485645

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1362480842882006

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.768740258002925

> <JCHEM_PKA_STRONGEST_BASIC>
3.998359170782524

> <JCHEM_POLAR_SURFACE_AREA>
232.59999999999994

> <JCHEM_REFRACTIVITY>
84.94139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenosine-diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

6022
  -OEChem-10231903253D

 42 44  0     1  0  0  0  0  0999 V2000
   -3.0310    1.0308    0.9657 P   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8752   -1.1051   -0.8725 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    1.6709    1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    2.3717   -1.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    4.2750   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5662    1.6947    1.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -0.1382   -0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8812    2.1443    0.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735    0.5673    2.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.8981   -1.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7324   -0.0856   -1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6815   -1.9735    0.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.0300    0.2230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755   -1.9507    0.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -0.8891    0.3117 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3453   -3.3282    0.2346 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456   -4.6341    0.0918 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    2.0484   -1.0710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3259    3.2696   -0.6722 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4014    1.4092    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4758    2.7376    0.4772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8591    2.1703    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085   -1.0242    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723   -0.6381    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -2.2058    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969   -3.3893    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -2.1000    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5324    1.3895   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7585    3.7052   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685    1.8535    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    3.4906    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7205    1.3439   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    2.9508   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    2.9981   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    5.0227    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952   -0.0752    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -2.1011    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3541   -4.6822    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -5.4800    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2591    2.9031    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3647   -2.6208   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5050   -0.4288   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  2  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  2  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 18  1  0  0  0  0
  4 34  1  0  0  0  0
  5 19  1  0  0  0  0
  5 35  1  0  0  0  0
  6 22  1  0  0  0  0
  8 40  1  0  0  0  0
 10 41  1  0  0  0  0
 11 42  1  0  0  0  0
 13 20  1  0  0  0  0
 13 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 24  2  0  0  0  0
 14 25  1  0  0  0  0
 15 23  2  0  0  0  0
 15 27  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  2  0  0  0  0
 17 26  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 28  1  0  0  0  0
 19 21  1  0  0  0  0
 19 29  1  0  0  0  0
 20 30  1  0  0  0  0
 21 22  1  0  0  0  0
 21 31  1  0  0  0  0
 22 32  1  0  0  0  0
 22 33  1  0  0  0  0
 23 25  1  0  0  0  0
 24 36  1  0  0  0  0
 25 26  2  0  0  0  0
 27 37  1  0  0  0  0
M  END
> <PUBCHEM_COMPOUND_CID>
6022

> <PUBCHEM_CONFORMER_RMSD>
0.8

> <PUBCHEM_CONFORMER_DIVERSEORDER>
18
124
374
67
65
340
182
307
273
287
208
276
214
354
89
110
293
216
244
256
341
28
297
235
330
12
33
261
242
271
266
203
128
192
328
49
220
84
79
151
316
156
168
365
80
329
29
290
186
291
136
333
222
296
8
73
57
100
249
202
258
25
305
304
233
292
142
243
150
51
37
360
106
135
75
45
269
93
164
60
56
326
232
379
264
201
245
4
99
34
323
97
337
265
219
213
194
166
115
163
324
206
22
134
301
143
207
113
270
212
14
155
175
339
63
148
107
338
159
351
246
191
302
196
48
378
250
180
171
53
231
278
237
19
176
141
123
229
76
218
377
7
165
226
306
251
11
126
130
209
369
88
263
149
36
211
82
185
167
366
334
31
66
44
173
268
332
300
58
376
131
200
116
121
13
78
373
272
288
275
234
160
303
39
315
358
38
24
236
52
350
199
96
299
190
283
20
68
205
344
114
215
26
86
274
122
108
147
62
139
335
183
336
50
257
240
23
325
46
41
153
17
357
221
259
133
349
129
352
81
70
125
225
198
281
345
239
21
132
35
317
55
184
228
47
372
59
224
90
170
146
223
74
71
103
383
87
255
230
169
248
127
172
15
32
178
112
193
241
370
162
111
144
318
342
381
197
102
154
138
321
137
30
277
364
353
109
189
294
177
83
157
368
119
253
117
343
254
320
27
5
331
64
3
314
104
145
346
118
6
85
16
279
371
252
362
286
158
247
308
43
382
217
298
42
311
92
262
91
375
187
120
2
77
289
210
69
280
174
9
295
1
367
105
204
95
284
161
356
313
348
101
282
359
260
195
140
188
227
72
98
361
238
312
285
380
61
40
181
152
179
54
355
267
309
94
319
10
347
363
322
327
310

> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
36
1 1.51
10 -0.77
11 -0.77
12 -0.7
13 0.05
14 -0.57
15 -0.57
16 -0.62
17 -0.9
18 0.28
19 0.28
2 1.51
20 0.54
21 0.28
22 0.28
23 0.11
24 0.04
25 0.23
26 0.41
27 0.47
3 -0.56
34 0.4
35 0.4
36 0.15
37 0.15
38 0.4
39 0.4
4 -0.68
40 0.5
41 0.5
42 0.5
5 -0.68
6 -0.55
7 -0.54
8 -0.77
9 -0.7

> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
7

> <PUBCHEM_PHARMACOPHORE_FEATURES>
19
1 10 acceptor
1 11 acceptor
1 12 acceptor
1 17 cation
1 17 donor
1 3 acceptor
1 4 acceptor
1 4 donor
1 5 acceptor
1 5 donor
1 8 acceptor
1 9 acceptor
3 13 14 24 cation
3 13 15 23 cation
3 15 16 27 cation
4 2 10 11 12 anion
5 13 14 23 24 25 rings
5 3 18 19 20 21 rings
6 15 16 23 25 26 27 rings

> <PUBCHEM_HEAVY_ATOM_COUNT>
27

> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
4

> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0

> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0

> <PUBCHEM_COMPONENT_COUNT>
1

> <PUBCHEM_CACTVS_TAUTO_COUNT>
3

> <PUBCHEM_CONFORMER_ID>
0000178600000012

> <PUBCHEM_MMFF94_ENERGY>
5.8677

> <PUBCHEM_FEATURE_SELFOVERLAP>
97.09

> <PUBCHEM_SHAPE_FINGERPRINT>
108634 29 17188970657971680332
12553582 1 18265619783841387642
12596599 1 17845383167108956895
13004483 165 17687179790364837361
13140716 1 18338806705644762474
138480 1 18337953394068585416
14117953 113 17406266630284732989
14790565 3 18265072317979012372
19591789 44 17977129042814796312
20645477 70 18187646933627237081
21634736 98 18342454871839635079
23559900 14 18337657673075789531
238 59 18263083382393889145
392239 28 17988067899648126288
46194498 28 17749390317579477837
463206 1 18338517417911614833

> <PUBCHEM_SHAPE_MULTIPOLES>
479.75
7.74
5.38
1.29
7.93
0.8
-0.18
2.03
-1.28
-4.43
-0.45
1.27
-0.36
-1.79

> <PUBCHEM_SHAPE_SELFOVERLAP>
995.652

> <PUBCHEM_SHAPE_VOLUME>
276

> <PUBCHEM_COORDINATE_TYPE>
2
5
10

$$$$

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  O   UNK     0    8664.3348663.039   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8667.6758663.024   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8668.6228666.498   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8669.9548665.726   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8671.2868666.498   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8672.6388665.752   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8670.5208667.832   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8672.0608667.832   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0    8673.9708666.521   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0    8673.2008667.855   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8675.3028665.752   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8674.7408667.855   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8666.0358666.648   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8665.2658664.278   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.8058664.278   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.2818665.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.5138666.704   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0    8659.0378665.239   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8660.0688664.094   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8661.5748664.415   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8662.0508665.879   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8661.0208667.024   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0    8663.4578666.505   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0    8663.2968668.037   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0    8661.7908668.357   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0    8658.4838667.848   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0    8664.7908665.735   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3    4   16                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5    9                                                       
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   16   27                                                       
CONECT   14   15    1   27                                                  
CONECT   15   14   16    2                                                  
CONECT   16   15   13    3                                                  
CONECT   17   22   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   20   18                                                       
CONECT   20   19   21                                                       
CONECT   21   22   23   20                                                  
CONECT   22   21   17   25                                                  
CONECT   23   24   21   27                                                  
CONECT   24   25   23                                                       
CONECT   25   24   22                                                       
CONECT   26   17                                                            
CONECT   27   23   14   13                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/NC1=NC=NC2=C1N=CN2%5BC@@H%5D1O%... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1       6.453   3.236   0.899  1.00  0.00           N  
HETATM    2  C   UNL     1       5.995   2.144   0.183  1.00  0.00           C  
HETATM    3  N   UNL     1       6.756   1.567  -0.741  1.00  0.00           N  
HETATM    4  C   UNL     1       6.327   0.525  -1.428  1.00  0.00           C  
HETATM    5  N   UNL     1       5.134  -0.001  -1.244  1.00  0.00           N  
HETATM    6  C   UNL     1       4.302   0.508  -0.341  1.00  0.00           C  
HETATM    7  C   UNL     1       4.715   1.614   0.421  1.00  0.00           C  
HETATM    8  N   UNL     1       3.693   1.929   1.254  1.00  0.00           N  
HETATM    9  C   UNL     1       2.704   1.107   1.056  1.00  0.00           C  
HETATM   10  N   UNL     1       3.033   0.208   0.085  1.00  0.00           N  
HETATM   11  C   UNL     1       2.183  -0.874  -0.418  1.00  0.00           C  
HETATM   12  H   UNL     1       2.343  -1.015  -1.488  1.00  0.00           H  
HETATM   13  O   UNL     1       0.793  -0.587  -0.151  1.00  0.00           O  
HETATM   14  C   UNL     1       0.122  -1.865  -0.215  1.00  0.00           C  
HETATM   15  H   UNL     1      -0.035  -2.159  -1.253  1.00  0.00           H  
HETATM   16  C   UNL     1      -1.214  -1.802   0.527  1.00  0.00           C  
HETATM   17  O   UNL     1      -2.101  -0.918  -0.162  1.00  0.00           O  
HETATM   18  P   UNL     1      -3.600  -0.613   0.340  1.00  0.00           P  
HETATM   19  O   UNL     1      -4.479  -1.959   0.256  1.00  0.00           O  
HETATM   20  O   UNL     1      -3.563  -0.134   1.740  1.00  0.00           O  
HETATM   21  O   UNL     1      -4.260   0.519  -0.597  1.00  0.00           O  
HETATM   22  P   UNL     1      -5.496   1.535  -0.421  1.00  0.00           P  
HETATM   23  O   UNL     1      -5.032   2.798   0.463  1.00  0.00           O  
HETATM   24  O   UNL     1      -5.983   2.043  -1.869  1.00  0.00           O  
HETATM   25  O   UNL     1      -6.612   0.840   0.259  1.00  0.00           O  
HETATM   26  C   UNL     1       1.083  -2.851   0.485  1.00  0.00           C  
HETATM   27  H   UNL     1       0.815  -2.964   1.536  1.00  0.00           H  
HETATM   28  O   UNL     1       1.067  -4.119  -0.174  1.00  0.00           O  
HETATM   29  C   UNL     1       2.472  -2.185   0.346  1.00  0.00           C  
HETATM   30  H   UNL     1       2.892  -1.968   1.329  1.00  0.00           H  
HETATM   31  O   UNL     1       3.357  -3.023  -0.401  1.00  0.00           O  
HETATM   32  H   UNL     1       7.340   3.590   0.728  1.00  0.00           H  
HETATM   33  H   UNL     1       5.886   3.650   1.568  1.00  0.00           H  
HETATM   34  H   UNL     1       6.978   0.087  -2.170  1.00  0.00           H  
HETATM   35  H   UNL     1       1.763   1.130   1.585  1.00  0.00           H  
HETATM   36  H   UNL     1      -1.654  -2.798   0.569  1.00  0.00           H  
HETATM   37  H   UNL     1      -1.050  -1.434   1.540  1.00  0.00           H  
HETATM   38  H   UNL     1      -4.547  -2.329  -0.635  1.00  0.00           H  
HETATM   39  H   UNL     1      -4.302   3.301   0.077  1.00  0.00           H  
HETATM   40  H   UNL     1      -6.727   2.660  -1.840  1.00  0.00           H  
HETATM   41  H   UNL     1       1.653  -4.777   0.225  1.00  0.00           H  
HETATM   42  H   UNL     1       3.523  -3.883   0.009  1.00  0.00           H  
CONECT    1    2   32   33                                            
CONECT    2    1    3    3    7                                       
CONECT    3    2    2    4                                            
CONECT    4    3    5    5   34                                       
CONECT    5    4    4    6                                            
CONECT    6    5    7    7   10                                       
CONECT    7    6    6    2    8                                       
CONECT    8    7    9    9                                            
CONECT    9    8    8   10   35                                       
CONECT   10    9    6   11                                            
CONECT   11   10   12   13   29                                       
CONECT   12   11                                                      
CONECT   13   11   14                                                 
CONECT   14   13   15   16   26                                       
CONECT   15   14                                                      
CONECT   16   14   17   36   37                                       
CONECT   17   16   18                                                 
CONECT   18   17   19   20   20                                       
CONECT   18   21                                                      
CONECT   19   18   38                                                 
CONECT   20   18   18                                                 
CONECT   21   18   22                                                 
CONECT   22   21   23   24   25                                       
CONECT   22   25                                                      
CONECT   23   22   39                                                 
CONECT   24   22   40                                                 
CONECT   25   22   22                                                 
CONECT   26   14   27   28   29                                       
CONECT   27   26                                                      
CONECT   28   26   41                                                 
CONECT   29   26   30   11   31                                       
CONECT   30   29                                                      
CONECT   31   29   42                                                 
CONECT   32    1                                                      
CONECT   33    1                                                      
CONECT   34    4                                                      
CONECT   35    9                                                      
CONECT   36   16                                                      
CONECT   37   16                                                      
CONECT   38   19                                                      
CONECT   39   23                                                      
CONECT   40   24                                                      
CONECT   41   28                                                      
CONECT   42   31                                                      
MASTER        0    0    0    0    0    0    0    0   42    0   42    0
END

6022
  -OEChem-10231903253D

42 44  0     1  0  0  0  0  0999 V2000
   -3.0310    1.0308    0.9657 P   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8752   -1.1051   -0.8725 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372    1.6709    1.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    2.3717   -1.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    4.2750   -0.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5662    1.6947    1.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145   -0.1382   -0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8812    2.1443    0.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6735    0.5673    2.2409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -1.8981   -1.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7324   -0.0856   -1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6815   -1.9735    0.0475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6465   -0.0300    0.2230 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755   -1.9507    0.1023 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -0.8891    0.3117 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3453   -3.3282    0.2346 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456   -4.6341    0.0918 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1310    2.0484   -1.0710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3259    3.2696   -0.6722 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4014    1.4092    0.2825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4758    2.7376    0.4772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8591    2.1703    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7085   -1.0242    0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723   -0.6381    0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -2.2058    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6969   -3.3893    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2229   -2.1000    0.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5324    1.3895   -1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7585    3.7052   -1.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2685    1.8535    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3102    3.4906    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7205    1.3439   -0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498    2.9508   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8263    2.9981   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    5.0227    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7952   -0.0752    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -2.1011    0.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3541   -4.6822    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -5.4800    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2591    2.9031    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3647   -2.6208   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5050   -0.4288   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  2  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 12  2  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 18  1  0  0  0  0
  4 34  1  0  0  0  0
  5 19  1  0  0  0  0
  5 35  1  0  0  0  0
  6 22  1  0  0  0  0
  8 40  1  0  0  0  0
 10 41  1  0  0  0  0
 11 42  1  0  0  0  0
 13 20  1  0  0  0  0
 13 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 24  2  0  0  0  0
 14 25  1  0  0  0  0
 15 23  2  0  0  0  0
 15 27  1  0  0  0  0
 16 26  1  0  0  0  0
 16 27  2  0  0  0  0
 17 26  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 28  1  0  0  0  0
 19 21  1  0  0  0  0
 19 29  1  0  0  0  0
 20 30  1  0  0  0  0
 21 22  1  0  0  0  0
 21 31  1  0  0  0  0
 22 32  1  0  0  0  0
 22 33  1  0  0  0  0
 23 25  1  0  0  0  0
 24 36  1  0  0  0  0
 25 26  2  0  0  0  0
 27 37  1  0  0  0  0
M  END
> <PUBCHEM_COMPOUND_CID>
6022

> <PUBCHEM_CONFORMER_RMSD>
0.8

> <PUBCHEM_CONFORMER_DIVERSEORDER>
18
124
374
67
65
340
182
307
273
287
208
276
214
354
89
110
293
216
244
256
341
28
297
235
330
12
33
261
242
271
266
203
128
192
328
49
220
84
79
151
316
156
168
365
80
329
29
290
186
291
136
333
222
296
8
73
57
100
249
202
258
25
305
304
233
292
142
243
150
51
37
360
106
135
75
45
269
93
164
60
56
326
232
379
264
201
245
4
99
34
323
97
337
265
219
213
194
166
115
163
324
206
22
134
301
143
207
113
270
212
14
155
175
339
63
148
107
338
159
351
246
191
302
196
48
378
250
180
171
53
231
278
237
19
176
141
123
229
76
218
377
7
165
226
306
251
11
126
130
209
369
88
263
149
36
211
82
185
167
366
334
31
66
44
173
268
332
300
58
376
131
200
116
121
13
78
373
272
288
275
234
160
303
39
315
358
38
24
236
52
350
199
96
299
190
283
20
68
205
344
114
215
26
86
274
122
108
147
62
139
335
183
336
50
257
240
23
325
46
41
153
17
357
221
259
133
349
129
352
81
70
125
225
198
281
345
239
21
132
35
317
55
184
228
47
372
59
224
90
170
146
223
74
71
103
383
87
255
230
169
248
127
172
15
32
178
112
193
241
370
162
111
144
318
342
381
197
102
154
138
321
137
30
277
364
353
109
189
294
177
83
157
368
119
253
117
343
254
320
27
5
331
64
3
314
104
145
346
118
6
85
16
279
371
252
362
286
158
247
308
43
382
217
298
42
311
92
262
91
375
187
120
2
77
289
210
69
280
174
9
295
1
367
105
204
95
284
161
356
313
348
101
282
359
260
195
140
188
227
72
98
361
238
312
285
380
61
40
181
152
179
54
355
267
309
94
319
10
347
363
322
327
310

> <PUBCHEM_MMFF94_PARTIAL_CHARGES>
36
1 1.51
10 -0.77
11 -0.77
12 -0.7
13 0.05
14 -0.57
15 -0.57
16 -0.62
17 -0.9
18 0.28
19 0.28
2 1.51
20 0.54
21 0.28
22 0.28
23 0.11
24 0.04
25 0.23
26 0.41
27 0.47
3 -0.56
34 0.4
35 0.4
36 0.15
37 0.15
38 0.4
39 0.4
4 -0.68
40 0.5
41 0.5
42 0.5
5 -0.68
6 -0.55
7 -0.54
8 -0.77
9 -0.7

> <PUBCHEM_EFFECTIVE_ROTOR_COUNT>
7

> <PUBCHEM_PHARMACOPHORE_FEATURES>
19
1 10 acceptor
1 11 acceptor
1 12 acceptor
1 17 cation
1 17 donor
1 3 acceptor
1 4 acceptor
1 4 donor
1 5 acceptor
1 5 donor
1 8 acceptor
1 9 acceptor
3 13 14 24 cation
3 13 15 23 cation
3 15 16 27 cation
4 2 10 11 12 anion
5 13 14 23 24 25 rings
5 3 18 19 20 21 rings
6 15 16 23 25 26 27 rings

> <PUBCHEM_HEAVY_ATOM_COUNT>
27

> <PUBCHEM_ATOM_DEF_STEREO_COUNT>
4

> <PUBCHEM_ATOM_UDEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_DEF_STEREO_COUNT>
0

> <PUBCHEM_BOND_UDEF_STEREO_COUNT>
0

> <PUBCHEM_ISOTOPIC_ATOM_COUNT>
0

> <PUBCHEM_COMPONENT_COUNT>
1

> <PUBCHEM_CACTVS_TAUTO_COUNT>
3

> <PUBCHEM_CONFORMER_ID>
0000178600000012

> <PUBCHEM_MMFF94_ENERGY>
5.8677

> <PUBCHEM_FEATURE_SELFOVERLAP>
97.09

> <PUBCHEM_SHAPE_FINGERPRINT>
108634 29 17188970657971680332
12553582 1 18265619783841387642
12596599 1 17845383167108956895
13004483 165 17687179790364837361
13140716 1 18338806705644762474
138480 1 18337953394068585416
14117953 113 17406266630284732989
14790565 3 18265072317979012372
19591789 44 17977129042814796312
20645477 70 18187646933627237081
21634736 98 18342454871839635079
23559900 14 18337657673075789531
238 59 18263083382393889145
392239 28 17988067899648126288
46194498 28 17749390317579477837
463206 1 18338517417911614833

> <PUBCHEM_SHAPE_MULTIPOLES>
479.75
7.74
5.38
1.29
7.93
0.8
-0.18
2.03
-1.28
-4.43
-0.45
1.27
-0.36
-1.79

> <PUBCHEM_SHAPE_SELFOVERLAP>
995.652

> <PUBCHEM_SHAPE_VOLUME>
276

> <PUBCHEM_COORDINATE_TYPE>
2
5
10

$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
5'-Adenylphosphoric acid	ChEBI
Adenosine 5'-diphosphate	ChEBI
ADENOSINE-5'-diphosphATE	ChEBI
H3ADP	ChEBI
5'-Adenylphosphate	Generator
Adenosine 5'-diphosphoric acid	Generator
ADENOSINE-5'-diphosphoric acid	Generator
Adenosindiphosphorsaeure	HMDB
Adenosine 5'-pyrophosphate	HMDB
Adenosine diphosphate	HMDB
Adenosine pyrophosphate	HMDB
Adenosine-5-diphosphate	HMDB
Adenosine-diphosphate	HMDB
5'-Pyrophosphate, adenosine	HMDB
Adenosine 5' pyrophosphate	HMDB
Diphosphate, adenosine	HMDB
Magnesium ADP	HMDB
MgADP	HMDB
Pyrophosphate, adenosine	HMDB
ADP, Magnesium	HMDB
Adenosine diphosphoric acid	HMDB
ADP	MeSH

Chemical Formula

C₁₀H₁₅N₅O₁₀P₂

Average Molecular Weight

427.2011

Monoisotopic Molecular Weight

427.029414749

IUPAC Name

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

Traditional Name

adenosine-diphosphate

CAS Registry Number

58-64-0

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

XTWYTFMLZFPYCI-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside diphosphates

Alternative Parents

Substituents

Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Imidolactam
Pyrimidine
Azole
Heteroaromatic compound
Imidazole
Tetrahydrofuran
Secondary alcohol
1,2-diol
Azacycle
Oxacycle
Organoheterocyclic compound
Alcohol
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Primary amine
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine ribonucleoside 5'-diphosphate (CHEBI:16761 )
adenosine 5'-phosphate (CHEBI:16761 )
Ribonucleotides (C00008 )

Ontology

Physiological effect

Health effect:

Health condition:

Nervous system disorders:

Stroke

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

All tissues

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.27 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-4.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.94 m³·mol⁻¹	ChemAxon
Polarizability	34.24 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

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5931200000-d741fb674f63c06ad31c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004j-9814310000-161f4ca9b901a0d2af95	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-5931200000-d741fb674f63c06ad31c	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0301900000-f65eba52a00479514d8e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-0900000000-cdad0c415295c75e0b67	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-1900000000-1f27fdf6dbd77cbe927d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0102981000-79c6771fae3255f75825	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0209000000-24c7ad0d0646786963be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-d266bbe08f0bcb8102b4	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000090000-8a788ef5a2c7ccc534e1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6900600000-fe2194fd2a27df917e5b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0209000000-24c7ad0d0646786963be	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-6900600000-fe2194fd2a27df917e5b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-002k-0809500000-7fdcfab442e6730d4fea	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000b-0809400000-73322c322a5e1ac31635	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000b-0809200000-2c8f8cd308e88cb92e57	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0911300000-0b0c309b755e7b5adfdb	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-1d631dbd3ed3927f1194	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-0e5039d8b3a6bd79b7d6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0900700000-ae031f4329b6e38885e8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3900000000-4c42d87cdde0e1918071	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-3eb64003e08db733f0e2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0200900000-66a6a98da30be5eadaad	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-ee05a7a47d9c043c0d38	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-83ae0a6e3f30ba5d18ac	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100900000-03dd84ac240093775e8e	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9301600000-695d718b6a48856c40e1	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-6a4005c5efea63c8abd8	2021-09-08	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H] 2D NMR Spectrum (predicted)	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Nucleus
Endoplasmic reticulum
Peroxisome

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Saliva
Urine

Tissue Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Histidine Metabolism
Lactose Synthesis		Not Available
Glycerolipid Metabolism
Ammonia Recycling
Glycolysis

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	160.0 +/- 14.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Cellular Cytoplasm	Detected and Quantified	270 (150-390) uM	Adult (>18 years old)	Both	Normal	15882454	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.90 +/- 0.025 uM	Adult (>18 years old)	Both	Normal	15993662	details
Saliva	Detected and Quantified	0.0257 +/- 0.0618 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.169 +/- 0.234 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.207 +/- 0.324 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.23 +/- 0.13 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	1.39 +/- 0.16 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	0.298 +/- 0.316 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.26 +/- 0.19 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	0.317 +/- 0.491 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.387 +/- 0.462 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.433 +/- 0.363 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	2.654 +/- 2.236 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	1.8 (1.0-3.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.10 +/- 0.60 uM	Adult (>18 years old)	Both	Rachialgia	15993662	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.91 +/- 0.46 uM	Adult (>18 years old)	Both	Subarachnoid hemorrhage	15993662	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.63 +/- 0.37 uM	Adult (>18 years old)	Both	Epilepsy	15993662	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.86 +/- 1.67 uM	Adult (>18 years old)	Both	Stroke	15993662	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.62 +/- 0.96 uM	Adult (>18 years old)	Both	Neuroinfection	15993662	details
Urine	Detected and Quantified	3.242 +/- 1.657 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Rachialgia
Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Subarachnoid hemorrhage
Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Epilepsy
Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Stroke
Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Neuroinfection
Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. [PubMed:15993662 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

105800 (Subarachnoid hemorrhage)
601367 (Stroke)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Adenosine_diphosphate

METLIN ID

6175

PubChem Compound

6022

PDB ID

Not Available

ChEBI ID

16761

Food Biomarker Ontology

Not Available

VMH ID

ADP

MarkerDB ID

MDB00000316

References

Synthesis Reference

Yamagata, Yukio. Prebiotic formation of ADP and ATP from AMP, calcium phosphates and cyanate in aqueous solution. Origins of Life and Evolution of the Biosphere (1999), 29(5), 511-520.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Quinton TM, Kim S, Jin J, Kunapuli SP: Lipid rafts are required in Galpha(i) signaling downstream of the P2Y12 receptor during ADP-mediated platelet activation. J Thromb Haemost. 2005 May;3(5):1036-41. [PubMed:15869601 ]
Saxena R, Gupta M, Gupta S, Kannan M, Ahmed RP, Choudhry VP: Inherited heterogenous defect in platelet aggregation selectively with ADP and epinephrine--a series of 25 cases. Indian J Pathol Microbiol. 2005 Jul;48(3):345-8. [PubMed:16761747 ]
Corsonello A, Malara A, De Domenico D, Damiano MC, Mirone S, Loddo S, Ientile R, Corica F: Effects of magnesium sulphate on leptin-dependent platelet aggregation: an ex vivo study. Magnes Res. 2005 Mar;18(1):7-11. [PubMed:15945611 ]
Cuisset T, Frere C, Quilici J, Barbou F, Morange PE, Hovasse T, Bonnet JL, Alessi MC: High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome. J Thromb Haemost. 2006 Mar;4(3):542-9. Epub 2005 Dec 22. [PubMed:16371119 ]
Imura Y, Stassen JM, Bunting S, Stockmans F, Collen D: Antithrombotic properties of L-cysteine, N-(mercaptoacetyl)-D-Tyr-Arg-Gly-Asp-sulfoxide (G4120) in a hamster platelet-rich femoral vein thrombosis model. Blood. 1992 Sep 1;80(5):1247-53. [PubMed:1515641 ]
Cuisset T, Frere C, Quilici J, Morange PE, Nait-Saidi L, Carvajal J, Lehmann A, Lambert M, Bonnet JL, Alessi MC: Benefit of a 600-mg loading dose of clopidogrel on platelet reactivity and clinical outcomes in patients with non-ST-segment elevation acute coronary syndrome undergoing coronary stenting. J Am Coll Cardiol. 2006 Oct 3;48(7):1339-45. Epub 2006 Sep 12. [PubMed:17010792 ]
Vigue C, Vigue L, Huszar G: Adenosine triphosphate (ATP) concentrations and ATP/adenosine diphosphate ratios in human sperm of normospermic, oligospermic, and asthenospermic specimens and in their swim-up fractions: lack of correlation between ATP parameters and sperm creatine kinase concentrations. J Androl. 1992 Jul-Aug;13(4):305-11. [PubMed:1399831 ]
Smith SM, Judge HM, Peters G, Storey RF: Multiple antiplatelet effects of clopidogrel are not modulated by statin type in patients undergoing percutaneous coronary intervention. Platelets. 2004 Dec;15(8):465-74. [PubMed:15763887 ]
Ji Q, Ghaly M, Hjemdahl P, Tornvall P, Li N: Contrast medium attenuates platelet activation and platelet-leukocyte cross-talk. Thromb Haemost. 2005 May;93(5):922-6. [PubMed:15886810 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
Morshedi M, Oehninger S, Blackmore P, Bocca S, Coddington C, Hodgen G: Investigation of some biochemical and functional effects of cryopreservation of human spermatozoa using an automated freezing-quick-thawing method. Int J Androl. 1995 Dec;18(6):279-86. [PubMed:8719843 ]
Hua J, Suguro S, Iwabuchi K, Tsutsumi-Ishii Y, Sakamoto K, Nagaoka I: Glucosamine, a naturally occurring amino monosaccharide, suppresses the ADP-mediated platelet activation in humans. Inflamm Res. 2004 Dec;53(12):680-8. [PubMed:15654516 ]
Shabanova EY, Mindukshev IV, Malakhovskaya EA, Vivulanets EV, Petrishchev NN, Krivchenko AI: Cooperative type of platelet hypersensitivity to ADP. Bull Exp Biol Med. 2005 Sep;140(3):282-4. [PubMed:16307036 ]

Only showing the first 10 proteins. There are 788 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UMP-CMP kinase

General function:: Involved in ATP binding
Specific function:: Catalyzes specific phosphoryl transfer from ATP to UMP and CMP.
Gene Name:: CMPK1
Uniprot ID:: P30085
Molecular weight:: 20180.12

Reactions

Adenosine triphosphate + (d)CMP → ADP + (d)CDP	details
Adenosine triphosphate + Uridine 5'-monophosphate → ADP + Uridine 5'-diphosphate	details
Adenosine triphosphate + Cytidine monophosphate → ADP + CDP	details
Adenosine triphosphate + dCMP → ADP + dCDP	details

Enzyme Details

2. Deoxycytidine kinase

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DCK
Uniprot ID:: P27707
Molecular weight:: 30518.315

Reactions

Adenosine triphosphate + Adenosine → ADP + Adenosine monophosphate	details
Adenosine triphosphate + Deoxycytidine → ADP + dCMP	details

Enzyme Details

3. ATP-citrate synthase

General function:: Involved in ATP citrate synthase activity
Specific function:: ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:: ACLY
Uniprot ID:: P53396
Molecular weight:: 120838.27

Reactions

ADP + Phosphate + Acetyl-CoA + Oxalacetic acid → Adenosine triphosphate + Citric acid + Coenzyme A	details
Adenosine triphosphate + Citric acid + Coenzyme A → ADP + Phosphate + Acetyl-CoA + Oxalacetic acid	details

Enzyme Details

4. Acetyl-CoA carboxylase 2

General function:: Involved in acetyl-CoA carboxylase activity
Specific function:: ACC-beta may be involved in the provision of malonyl-CoA or in the regulation of fatty acid oxidation, rather than fatty acid biosynthesis. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:: ACACB
Uniprot ID:: O00763
Molecular weight:: 276538.575

Reactions

Adenosine triphosphate + Acetyl-CoA + Hydrogen carbonate → ADP + Phosphate + Malonyl-CoA	details
Adenosine triphosphate + biotin-[carboxyl-carrier-protein] + CO(2) → ADP + Phosphate + carboxy-biotin-[carboxyl-carrier-protein]	details
Adenosine triphosphate + Holo-[carboxylase] + Hydrogen carbonate → ADP + Phosphate + Carboxybiotin-carboxyl-carrier protein	details

Enzyme Details

5. Pyruvate carboxylase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:: PC
Uniprot ID:: P11498
Molecular weight:: 129632.565

Reactions

Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate → ADP + Phosphate + Oxalacetic acid	details

Enzyme Details

6. Acetyl-CoA carboxylase 1

General function:: Involved in acetyl-CoA carboxylase activity
Specific function:: Catalyzes the rate-limiting reaction in the biogenesis of long-chain fatty acids. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:: ACACA
Uniprot ID:: Q13085
Molecular weight:: 269997.01

Reactions

Adenosine triphosphate + Acetyl-CoA + Hydrogen carbonate → ADP + Phosphate + Malonyl-CoA	details
Adenosine triphosphate + biotin-[carboxyl-carrier-protein] + CO(2) → ADP + Phosphate + carboxy-biotin-[carboxyl-carrier-protein]	details
Adenosine triphosphate + Holo-[carboxylase] + Hydrogen carbonate → ADP + Phosphate + Carboxybiotin-carboxyl-carrier protein	details

Enzyme Details

7. Thymidylate kinase

General function:: Involved in thymidylate kinase activity
Specific function:: Catalyzes the conversion of dTMP to dTDP.
Gene Name:: DTYMK
Uniprot ID:: P23919
Molecular weight:: 23819.105

Reactions

Adenosine triphosphate + 5-Thymidylic acid → ADP + dTDP	details
Adenosine triphosphate + dUMP → ADP + dUDP	details

Enzyme Details

8. Ectonucleoside triphosphate diphosphohydrolase 1

General function:: Involved in hydrolase activity
Specific function:: In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:: ENTPD1
Uniprot ID:: P49961
Molecular weight:: 58706.0

Reactions

Adenosine triphosphate + Water → ADP + Phosphate	details
ADP + Water → Adenosine monophosphate + Phosphate	details

Enzyme Details

9. Soluble calcium-activated nucleotidase 1

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:: CANT1
Uniprot ID:: Q8WVQ1
Molecular weight:: 44839.24

Enzyme Details

10. Ectonucleoside triphosphate diphosphohydrolase 3

General function:: Involved in hydrolase activity
Specific function:: Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:: ENTPD3
Uniprot ID:: O75355
Molecular weight:: 59104.76

Reactions

Adenosine triphosphate + Water → ADP + Phosphate	details
ADP + Water → Adenosine monophosphate + Phosphate	details

Transporters

Enzyme Details

1. Copper-transporting ATPase 2

General function:: Involved in ATP binding
Specific function:: Involved in the export of copper out of the cells, such as the efflux of hepatic copper into the bile.
Gene Name:: ATP7B
Uniprot ID:: P35670
Molecular weight:: 157261.34

Enzyme Details

2. Copper-transporting ATPase 1

General function:: Involved in ATP binding
Specific function:: May supply copper to copper-requiring proteins within the secretory pathway, when localized in the trans-Golgi network. Under conditions of elevated extracellular copper, it relocalized to the plasma membrane where it functions in the efflux of copper from cells.
Gene Name:: ATP7A
Uniprot ID:: Q04656
Molecular weight:: 163372.275

Only showing the first 10 proteins. There are 788 proteins in total.

Show all enzymes and transporters

Showing metabocard for ADP (HMDB0001341)

MOL for HMDB0001341 (ADP)

3D MOL for HMDB0001341 (ADP)

3D SDF for HMDB0001341 (ADP)

3D-SDF for HMDB0001341 (ADP)

PDB for HMDB0001341 (ADP)

3D PDB for HMDB0001341 (ADP)

SMILES for HMDB0001341 (ADP)

INCHI for HMDB0001341 (ADP)

Structure for HMDB0001341 (ADP)

3D Structure for HMDB0001341 (ADP)

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions

Reactions

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Reactions

Transporters