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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (3) Show 7 proteins XML

enzymes (4)transporters (3) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015110

Secondary Accession Numbers

HMDB15110

Metabolite Identification

Common Name

Dipyridamole

Description

Dipyridamole is only found in individuals that have used or taken this drug. It is a phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimulates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation.

Structure

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

975
  Mrv0541 02231215092D          

 36 39  0  0  0  0            999 V2000
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    9.2844    2.9244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1079   -1.6644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.6642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8650   -0.4155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0015110
     RDKit          3D
Dipyridamole
 76 79  0  0  0  0  0  0  0  0999 V2000
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M  END

975
  Mrv0541 02231215092D          

 36 39  0  0  0  0            999 V2000
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  7 27  1  0  0  0  0
  8 24  2  0  0  0  0
  8 28  1  0  0  0  0
  9 25  1  0  0  0  0
  9 27  2  0  0  0  0
 10 26  1  0  0  0  0
 10 28  2  0  0  0  0
 11 27  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 28  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 22  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 29 33  1  0  0  0  0
 30 34  1  0  0  0  0
 31 35  1  0  0  0  0
 32 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015110

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

> <INCHI_KEY>
IZEKFCXSFNUWAM-UHFFFAOYSA-N

> <FORMULA>
C24H40N8O4

> <MOLECULAR_WEIGHT>
504.6256

> <EXACT_MASS>
504.317251808

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
56.93560309238033

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
1.8063892579999996

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.397674874739518

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.971635374201803

> <JCHEM_PKA_STRONGEST_BASIC>
6.587026987047743

> <JCHEM_POLAR_SURFACE_AREA>
145.44

> <JCHEM_REFRACTIVITY>
142.77939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dipyridamole

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015110
     RDKit          3D
Dipyridamole
 76 79  0  0  0  0  0  0  0  0999 V2000
   -6.8142    0.1964    1.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -0.5792    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9844   -0.2420    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.0878   -0.0442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -2.4985   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -2.8928   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -2.3839   -2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077   -0.4912    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961    0.8438    0.2198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.4969    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    2.9021    0.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    3.5420    1.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262    4.9790    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191    5.1617   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    4.7453   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    3.7286   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    0.7207    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    1.3008    0.2500 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152    0.5359    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5235    1.1160    0.2097 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    2.5329    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2718    2.7802    1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502    2.2275    2.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682    0.2519    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.5720   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4897   -0.2793   -1.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -0.7896   -0.0669 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9350   -1.4454   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -2.8469   -0.3550 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -3.7552    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -4.9677    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725   -5.4632   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -4.8482   -1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -3.3722   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1966   -0.6449   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -1.2226   -0.0946 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6087    1.1069    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9274   -1.6342    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9747   -0.3210    2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575   -0.3185   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569    0.8136    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970   -2.9430    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -2.9463   -0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3421   -4.0115   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5107   -2.6789   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -2.8967   -3.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    3.4885    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    3.0188    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879    5.3782    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173    5.5879    1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503    4.6376   -0.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    6.2634   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184    5.6097   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489    4.2839   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3872    3.1132   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6787    4.2774    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236    2.9985   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    3.0192    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    3.8672    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    2.3857    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    2.1954    2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3602    0.3597    0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.8057   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    0.3778   -2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6842    1.6502   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3352    0.2425   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -3.2393    1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904   -4.0918    0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -5.7777    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8356   -4.7809    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777   -6.5749   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -5.2225   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -4.9758   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880   -5.3031   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -3.1302   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9439   -2.8464   -2.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  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
 15 16  1  0
 10 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 28 35  1  0
 35 36  2  0
 36  8  1  0
 16 11  1  0
 35 17  1  0
 34 29  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 30 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  0
 33 74  1  0
 34 75  1  0
 34 76  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 975                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      20.016   0.849   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      17.331   5.459   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -5.364   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.907  -0.743   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      13.268  -3.107   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      10.576   3.107   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      14.681  -0.776   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       9.242   0.797   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      13.286   1.620   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      10.576  -1.513   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      16.012   1.604   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       7.908  -1.513   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      11.926  -3.861   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.593  -3.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.909   3.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.908  -5.401   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.575  -5.432   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.909   5.417   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.242   5.417   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.232  -6.187   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.576   6.187   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.286  -1.567   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.576   1.567   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.909   0.797   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.909  -0.743   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.681   0.829   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.242  -0.743   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.349   0.839   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.006   3.144   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.908  -3.053   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.574  -0.743   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.679   1.614   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.337   3.919   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.574  -3.824   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.241  -1.513   0.000  0.00  0.00           C+0
CONECT    1   33                                                            
CONECT    2   34                                                            
CONECT    3   35                                                            
CONECT    4   36                                                            
CONECT    5   13   14   23                                                  
CONECT    6   15   16   24                                                  
CONECT    7   23   27                                                       
CONECT    8   24   28                                                       
CONECT    9   25   27                                                       
CONECT   10   26   28                                                       
CONECT   11   27   29   30                                                  
CONECT   12   28   31   32                                                  
CONECT   13    5   17                                                       
CONECT   14    5   18                                                       
CONECT   15    6   19                                                       
CONECT   16    6   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   21                                                       
CONECT   19   15   22                                                       
CONECT   20   16   22                                                       
CONECT   21   17   18                                                       
CONECT   22   19   20                                                       
CONECT   23    5    7   26                                                  
CONECT   24    6    8   25                                                  
CONECT   25    9   24   26                                                  
CONECT   26   10   23   25                                                  
CONECT   27    7    9   11                                                  
CONECT   28    8   10   12                                                  
CONECT   29   11   33                                                       
CONECT   30   11   34                                                       
CONECT   31   12   35                                                       
CONECT   32   12   36                                                       
CONECT   33    1   29                                                       
CONECT   34    2   30                                                       
CONECT   35    3   31                                                       
CONECT   36    4   32                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

COMPND    HMDB0015110
HETATM    1  O1  UNL     1      -6.814   0.196   1.586  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.671  -0.579   1.397  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.984  -0.242   0.094  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.801  -1.088  -0.044  1.00  0.00           N  
HETATM    5  C3  UNL     1      -3.886  -2.498  -0.247  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.451  -2.893  -1.589  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.645  -2.384  -2.600  1.00  0.00           O  
HETATM    8  C5  UNL     1      -2.508  -0.491   0.025  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.396   0.844   0.220  1.00  0.00           N  
HETATM   10  C6  UNL     1      -1.225   1.497   0.302  1.00  0.00           C  
HETATM   11  N3  UNL     1      -1.214   2.902   0.504  1.00  0.00           N  
HETATM   12  C7  UNL     1      -0.598   3.542   1.631  1.00  0.00           C  
HETATM   13  C8  UNL     1      -0.326   4.979   1.301  1.00  0.00           C  
HETATM   14  C9  UNL     1       0.119   5.162  -0.117  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.948   4.745  -1.105  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.870   3.729  -0.490  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.088   0.721   0.176  1.00  0.00           C  
HETATM   18  N4  UNL     1       1.111   1.301   0.250  1.00  0.00           N  
HETATM   19  C13 UNL     1       2.215   0.536   0.127  1.00  0.00           C  
HETATM   20  N5  UNL     1       3.524   1.116   0.210  1.00  0.00           N  
HETATM   21  C14 UNL     1       3.662   2.533   0.462  1.00  0.00           C  
HETATM   22  C15 UNL     1       4.272   2.780   1.838  1.00  0.00           C  
HETATM   23  O3  UNL     1       3.450   2.227   2.808  1.00  0.00           O  
HETATM   24  C16 UNL     1       4.668   0.252   0.032  1.00  0.00           C  
HETATM   25  C17 UNL     1       5.405   0.572  -1.263  1.00  0.00           C  
HETATM   26  O4  UNL     1       6.490  -0.279  -1.393  1.00  0.00           O  
HETATM   27  N6  UNL     1       2.103  -0.790  -0.067  1.00  0.00           N  
HETATM   28  C18 UNL     1       0.935  -1.445  -0.152  1.00  0.00           C  
HETATM   29  N7  UNL     1       0.847  -2.847  -0.355  1.00  0.00           N  
HETATM   30  C19 UNL     1       0.210  -3.755   0.576  1.00  0.00           C  
HETATM   31  C20 UNL     1       1.069  -4.968   0.855  1.00  0.00           C  
HETATM   32  C21 UNL     1       1.773  -5.463  -0.384  1.00  0.00           C  
HETATM   33  C22 UNL     1       1.155  -4.848  -1.626  1.00  0.00           C  
HETATM   34  C23 UNL     1       1.443  -3.372  -1.578  1.00  0.00           C  
HETATM   35  C24 UNL     1      -0.197  -0.645  -0.023  1.00  0.00           C  
HETATM   36  N8  UNL     1      -1.390  -1.223  -0.095  1.00  0.00           N  
HETATM   37  H1  UNL     1      -6.609   1.107   1.274  1.00  0.00           H  
HETATM   38  H2  UNL     1      -5.927  -1.634   1.498  1.00  0.00           H  
HETATM   39  H3  UNL     1      -4.975  -0.321   2.234  1.00  0.00           H  
HETATM   40  H4  UNL     1      -5.657  -0.318  -0.774  1.00  0.00           H  
HETATM   41  H5  UNL     1      -4.657   0.814   0.158  1.00  0.00           H  
HETATM   42  H6  UNL     1      -4.497  -2.943   0.590  1.00  0.00           H  
HETATM   43  H7  UNL     1      -2.882  -2.946  -0.133  1.00  0.00           H  
HETATM   44  H8  UNL     1      -4.342  -4.011  -1.659  1.00  0.00           H  
HETATM   45  H9  UNL     1      -5.511  -2.679  -1.703  1.00  0.00           H  
HETATM   46  H10 UNL     1      -3.717  -2.897  -3.442  1.00  0.00           H  
HETATM   47  H11 UNL     1      -1.306   3.488   2.485  1.00  0.00           H  
HETATM   48  H12 UNL     1       0.329   3.019   1.942  1.00  0.00           H  
HETATM   49  H13 UNL     1       0.488   5.378   1.949  1.00  0.00           H  
HETATM   50  H14 UNL     1      -1.217   5.588   1.526  1.00  0.00           H  
HETATM   51  H15 UNL     1       1.050   4.638  -0.328  1.00  0.00           H  
HETATM   52  H16 UNL     1       0.280   6.263  -0.271  1.00  0.00           H  
HETATM   53  H17 UNL     1      -1.518   5.610  -1.486  1.00  0.00           H  
HETATM   54  H18 UNL     1      -0.449   4.284  -1.983  1.00  0.00           H  
HETATM   55  H19 UNL     1      -2.387   3.113  -1.269  1.00  0.00           H  
HETATM   56  H20 UNL     1      -2.679   4.277   0.032  1.00  0.00           H  
HETATM   57  H21 UNL     1       4.324   2.998  -0.282  1.00  0.00           H  
HETATM   58  H22 UNL     1       2.675   3.019   0.377  1.00  0.00           H  
HETATM   59  H23 UNL     1       4.346   3.867   2.037  1.00  0.00           H  
HETATM   60  H24 UNL     1       5.300   2.386   1.870  1.00  0.00           H  
HETATM   61  H25 UNL     1       2.511   2.195   2.507  1.00  0.00           H  
HETATM   62  H26 UNL     1       5.360   0.360   0.890  1.00  0.00           H  
HETATM   63  H27 UNL     1       4.341  -0.806  -0.023  1.00  0.00           H  
HETATM   64  H28 UNL     1       4.719   0.378  -2.123  1.00  0.00           H  
HETATM   65  H29 UNL     1       5.684   1.650  -1.301  1.00  0.00           H  
HETATM   66  H30 UNL     1       7.335   0.242  -1.528  1.00  0.00           H  
HETATM   67  H31 UNL     1       0.049  -3.239   1.548  1.00  0.00           H  
HETATM   68  H32 UNL     1      -0.790  -4.092   0.234  1.00  0.00           H  
HETATM   69  H33 UNL     1       0.406  -5.778   1.229  1.00  0.00           H  
HETATM   70  H34 UNL     1       1.836  -4.781   1.621  1.00  0.00           H  
HETATM   71  H35 UNL     1       1.678  -6.575  -0.507  1.00  0.00           H  
HETATM   72  H36 UNL     1       2.859  -5.222  -0.356  1.00  0.00           H  
HETATM   73  H37 UNL     1       0.064  -4.976  -1.593  1.00  0.00           H  
HETATM   74  H38 UNL     1       1.588  -5.303  -2.525  1.00  0.00           H  
HETATM   75  H39 UNL     1       2.520  -3.130  -1.544  1.00  0.00           H  
HETATM   76  H40 UNL     1       0.944  -2.846  -2.434  1.00  0.00           H  
CONECT    1    2   37
CONECT    2    3   38   39
CONECT    3    4   40   41
CONECT    4    5    8
CONECT    5    6   42   43
CONECT    6    7   44   45
CONECT    7   46
CONECT    8    9    9   36
CONECT    9   10
CONECT   10   11   17   17
CONECT   11   12   16
CONECT   12   13   47   48
CONECT   13   14   49   50
CONECT   14   15   51   52
CONECT   15   16   53   54
CONECT   16   55   56
CONECT   17   18   35
CONECT   18   19   19
CONECT   19   20   27
CONECT   20   21   24
CONECT   21   22   57   58
CONECT   22   23   59   60
CONECT   23   61
CONECT   24   25   62   63
CONECT   25   26   64   65
CONECT   26   66
CONECT   27   28   28
CONECT   28   29   35
CONECT   29   30   34
CONECT   30   31   67   68
CONECT   31   32   69   70
CONECT   32   33   71   72
CONECT   33   34   73   74
CONECT   34   75   76
CONECT   35   36   36
END

HMDB0015110
     RDKit          3D
Dipyridamole
 76 79  0  0  0  0  0  0  0  0999 V2000
   -6.8142    0.1964    1.5855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -0.5792    1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9844   -0.2420    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -1.0878   -0.0442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8858   -2.4985   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -2.8928   -1.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -2.3839   -2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077   -0.4912    0.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961    0.8438    0.2198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.4969    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143    2.9021    0.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983    3.5420    1.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3262    4.9790    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191    5.1617   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    4.7453   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8700    3.7286   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0884    0.7207    0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    1.3008    0.2500 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152    0.5359    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5235    1.1160    0.2097 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620    2.5329    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2718    2.7802    1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4502    2.2275    2.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682    0.2519    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.5720   -1.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4897   -0.2793   -1.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -0.7896   -0.0669 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9350   -1.4454   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472   -2.8469   -0.3550 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099   -3.7552    0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686   -4.9677    0.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725   -5.4632   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -4.8482   -1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -3.3722   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1966   -0.6449   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900   -1.2226   -0.0946 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6087    1.1069    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9274   -1.6342    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9747   -0.3210    2.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6575   -0.3185   -0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6569    0.8136    0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970   -2.9430    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824   -2.9463   -0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3421   -4.0115   -1.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5107   -2.6789   -1.7032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7174   -2.8967   -3.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    3.4885    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3291    3.0188    1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879    5.3782    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173    5.5879    1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0503    4.6376   -0.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    6.2634   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184    5.6097   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489    4.2839   -1.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3872    3.1132   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6787    4.2774    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236    2.9985   -0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747    3.0192    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464    3.8672    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    2.3857    1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    2.1954    2.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3602    0.3597    0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3407   -0.8057   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7194    0.3778   -2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6842    1.6502   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3352    0.2425   -1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -3.2393    1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7904   -4.0918    0.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055   -5.7777    1.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8356   -4.7809    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777   -6.5749   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -5.2225   -0.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -4.9758   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5880   -5.3031   -2.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5200   -3.1302   -1.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9439   -2.8464   -2.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  4  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
 15 16  1  0
 10 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 19 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 28 35  1  0
 35 36  2  0
 36  8  1  0
 16 11  1  0
 35 17  1  0
 34 29  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  0
 22 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
 25 65  1  0
 26 66  1  0
 30 67  1  0
 30 68  1  0
 31 69  1  0
 31 70  1  0
 32 71  1  0
 32 72  1  0
 33 73  1  0
 33 74  1  0
 34 75  1  0
 34 76  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cardoxin	ChEBI
Cleridium 150	ChEBI
Curantyl	ChEBI
Dipiridamol	ChEBI
Dipyridamine	ChEBI
Dipyridamolum	ChEBI
Dipyudamine	ChEBI
Dypyridamol	ChEBI
Persantin	ChEBI
Persantine	Kegg
Dipyridamol	HMDB
Usaf ge-12	HMDB
Ashbourne brand OF dipyridamole	HMDB
Berlin chemie brand OF dipyridamole	HMDB
Berlin-chemie brand OF dipyridamole	HMDB
Curantil	HMDB
Novo-dipiradol	HMDB
Novopharm brand OF dipyridamole	HMDB
Boehringer ingelheim brand OF dipyridamole	HMDB
Cléridium	HMDB
Dipyramidole	HMDB
Antistenocardin	HMDB
Apo-dipyridamole	HMDB
Cerebrovase	HMDB
Miosen	HMDB
Apotex brand OF dipyridamole	HMDB
Belmac brand OF dipyridamole	HMDB
IPRAD brand OF dipyridamole	HMDB
Kurantil	HMDB
Novo dipiradol	HMDB
Apo dipyridamole	HMDB

Chemical Formula

C₂₄H₄₀N₈O₄

Average Molecular Weight

504.6256

Monoisotopic Molecular Weight

504.317251808

IUPAC Name

2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol

Traditional Name

dipyridamole

CAS Registry Number

58-32-2

SMILES

OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1

InChI Identifier

InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

InChI Key

IZEKFCXSFNUWAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
Aminopyrimidine
Piperidine
Pyrimidine
Imidolactam
Heteroaromatic compound
Organoheterocyclic compound
Alkanolamine
Azacycle
Alcohol
Hydrocarbon derivative
Primary alcohol
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:4653 )
tertiary amino compound (CHEBI:4653 )
tetrol (CHEBI:4653 )
pyrimidopyrimidine (CHEBI:4653 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015110)
Membrane (HMDB: HMDB0015110)

Source

Exogenous

Exogenous (HMDB: HMDB0015110)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dipyridamole (Antiplatelet) Action Pathway (PathBank: SMP0000264)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.92 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	227.5	30932474
[M+H]+	Not Available	223.924	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000707

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
logP	1.52	ALOGPS
logP	1.81	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.97	ChemAxon
pKa (Strongest Basic)	6.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	145.44 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	142.78 m³·mol⁻¹	ChemAxon
Polarizability	56.94 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	216.006	31661259
DarkChem	[M-H]-	208.859	31661259
DeepCCS	[M+H]+	221.497	30932474
DeepCCS	[M-H]-	219.139	30932474
DeepCCS	[M-2H]-	252.614	30932474
DeepCCS	[M+Na]+	227.79	30932474
AllCCS	[M+H]+	215.9	32859911
AllCCS	[M+H-H2O]+	214.5	32859911
AllCCS	[M+NH4]+	217.2	32859911
AllCCS	[M+Na]+	217.6	32859911
AllCCS	[M-H]-	203.8	32859911
AllCCS	[M+Na-2H]-	205.3	32859911
AllCCS	[M+HCOO]-	207.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.55 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4977 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.43 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	177.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1276.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	197.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	381.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	457.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	678.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	802.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	299.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1603.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	756.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	292.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	152.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dipyridamole	OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1	2542.0	Standard polar	33892256
Dipyridamole	OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1	4289.0	Standard non polar	33892256
Dipyridamole	OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1	4514.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dipyridamole,1TMS,isomer #1	C[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1	4374.7	Semi standard non polar	33892256
Dipyridamole,2TMS,isomer #1	C[Si](C)(C)OCCN(CCO[Si](C)(C)C)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1	4267.0	Semi standard non polar	33892256
Dipyridamole,2TMS,isomer #2	C[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO[Si](C)(C)C)N=C(N3CCCCC3)C2=N1	4264.8	Semi standard non polar	33892256
Dipyridamole,3TMS,isomer #1	C[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO[Si](C)(C)C)CCO[Si](C)(C)C)N=C(N3CCCCC3)C2=N1	4159.3	Semi standard non polar	33892256
Dipyridamole,4TMS,isomer #1	C[Si](C)(C)OCCN(CCO[Si](C)(C)C)C1=NC(N2CCCCC2)=C2N=C(N(CCO[Si](C)(C)C)CCO[Si](C)(C)C)N=C(N3CCCCC3)C2=N1	4100.8	Semi standard non polar	33892256
Dipyridamole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1	4522.3	Semi standard non polar	33892256
Dipyridamole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN(CCO[Si](C)(C)C(C)(C)C)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=N1	4537.1	Semi standard non polar	33892256
Dipyridamole,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO)CCO[Si](C)(C)C(C)(C)C)N=C(N3CCCCC3)C2=N1	4534.5	Semi standard non polar	33892256
Dipyridamole,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCN(CCO)C1=NC(N2CCCCC2)=C2N=C(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)N=C(N3CCCCC3)C2=N1	4559.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dipyridamole GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1013900000-667f6d46e6523b3a3d7a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dipyridamole GC-MS (2 TMS) - 70eV, Positive	splash10-01c1-4100079000-4c029f3c81b99fb85ae2	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole LC-ESI-qTof , Positive-QTOF	splash10-0udl-0291000000-caeb14eb3ea863e020a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole LC-ESI-qTof , Positive-QTOF	splash10-0udl-0291000000-2fc7956fe6ea13c73317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole , positive-QTOF	splash10-0udl-0291000000-2fc7956fe6ea13c73317	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole , positive-QTOF	splash10-0a4i-0001190000-346cf73a19cbefa2dc11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole , positive-QTOF	splash10-0a4i-0013490000-839580758bc83767be8f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole , positive-QTOF	splash10-0udl-0291000000-caeb14eb3ea863e020a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dipyridamole , positive-QTOF	splash10-0a4i-1348890000-aa1e3a113b8c2768cb08	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 10V, Positive-QTOF	splash10-0a4i-0000390000-b9d4def1784057f522a6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 20V, Positive-QTOF	splash10-0btl-0000920000-cc12b54862b2bcd1ab8d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 40V, Positive-QTOF	splash10-016u-2003900000-53a9a6cb60455cac32e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 10V, Negative-QTOF	splash10-0udi-0000590000-50fb399e1dbe0355c7b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 20V, Negative-QTOF	splash10-0zfr-2000930000-1d8f7f2a171ae388588e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 40V, Negative-QTOF	splash10-014i-1001900000-f3010c0eafbeb9e97741	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 10V, Positive-QTOF	splash10-0a4i-0000090000-26e1f92d5f10dd7af547	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 20V, Positive-QTOF	splash10-0a4i-0000490000-5e1743c992f893c13776	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 40V, Positive-QTOF	splash10-0006-0001910000-61e2845ea7c59a8ca2d9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 10V, Negative-QTOF	splash10-0udi-0000090000-c0b4fa18532ec9c61047	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 20V, Negative-QTOF	splash10-014i-0000900000-360b0b12c29f6afe3e17	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipyridamole 40V, Negative-QTOF	splash10-0a4l-3203920000-e5a412f24717be48fd32	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Dipyridamole (Antiplatelet) Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00975	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00975	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00975

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2997

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dipyridamole

METLIN ID

Not Available

PubChem Compound

3108

PDB ID

Not Available

ChEBI ID

4653

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Diener HC, Cunha L, Forbes C, Sivenius J, Smets P, Lowenthal A: European Stroke Prevention Study. 2. Dipyridamole and acetylsalicylic acid in the secondary prevention of stroke. J Neurol Sci. 1996 Nov;143(1-2):1-13. [PubMed:8981292 ]

Enzymes

Enzyme Details

1. cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Gene Name:: PDE10A
Uniprot ID:: Q9Y233
Molecular weight:: 89388.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Fujishige K, Kotera J, Michibata H, Yuasa K, Takebayashi S, Okumura K, Omori K: Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A). J Biol Chem. 1999 Jun 25;274(26):18438-45. [PubMed:10373451 ]

Enzyme Details

2. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. cGMP-specific 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP.
Gene Name:: PDE5A
Uniprot ID:: O76074
Molecular weight:: 99984.14

References

Kulkarni SK, Patil CS: Phosphodiesterase 5 enzyme and its inhibitors: update on pharmacological and therapeutical aspects. Methods Find Exp Clin Pharmacol. 2004 Dec;26(10):789-99. [PubMed:15672122 ]
Santini F, Casali G, Franchi G, Auriemma S, Lusini M, Barozzi L, Favaro A, Messina A, Mazzucco A: Hemodynamic effects of inhaled nitric oxide and phosphodiesterase inhibitor (dipyridamole) on secondary pulmonary hypertension following heart valve surgery in adults. Int J Cardiol. 2005 Aug 18;103(2):156-63. [PubMed:16080974 ]
Kruuse C, Lassen LH, Iversen HK, Oestergaard S, Olesen J: Dipyridamole may induce migraine in patients with migraine without aura. Cephalalgia. 2006 Aug;26(8):925-33. [PubMed:16886928 ]
Jackson EK, Ren J, Zacharia LC, Mi Z: Characterization of renal ecto-phosphodiesterase. J Pharmacol Exp Ther. 2007 May;321(2):810-5. Epub 2007 Feb 16. [PubMed:17308037 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. Adenosine deaminase

General function:: Involved in deaminase activity
Specific function:: Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:: ADA
Uniprot ID:: P00813
Molecular weight:: 40764.13

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]

Enzyme Details

2. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

van Aubel RA, Smeets PH, Peters JG, Bindels RJ, Russel FG: The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol. 2002 Mar;13(3):595-603. [PubMed:11856762 ]
Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]
Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481 ]

Enzyme Details

3. Multidrug resistance-associated protein 5

General function:: Involved in ATP binding
Specific function:: Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:: ABCC5
Uniprot ID:: O15440
Molecular weight:: 160658.8

References

Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]

Showing metabocard for Dipyridamole (HMDB0015110)

MOL for HMDB0015110 (Dipyridamole)

3D MOL for HMDB0015110 (Dipyridamole)

3D SDF for HMDB0015110 (Dipyridamole)

3D-SDF for HMDB0015110 (Dipyridamole)

PDB for HMDB0015110 (Dipyridamole)

3D PDB for HMDB0015110 (Dipyridamole)

SMILES for HMDB0015110 (Dipyridamole)

INCHI for HMDB0015110 (Dipyridamole)

Structure for HMDB0015110 (Dipyridamole)

3D Structure for HMDB0015110 (Dipyridamole)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References

References

References