NP-MRD: Showing NP-Card for Clopidogrel (NP0334579)

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Record Information

Version

2.0

Created at

2024-09-10 18:59:21 UTC

Updated at

2024-09-10 18:59:22 UTC

NP-MRD ID

NP0334579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Clopidogrel

Description

Clopidogrel, also known as plavix or isocover, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Clopidogrel is a very strong basic compound (based on its pKa). Within humans, clopidogrel participates in a number of enzymatic reactions. In particular, clopidogrel can be converted into 2-oxoclopidogrel; which is catalyzed by the enzymes cytochrome P450 1A2, cytochrome P450 2B6, and cytochrome P450 2C19. In addition, clopidogrel can be converted into clopidogrel; which is catalyzed by the enzyme multidrug resistance protein 1. Clopidogrel was first documented in 2003 (PMID: 14502454). In humans, clopidogrel is involved in clopidogrel action pathway (PMID: 15976759) (PMID: 16454979) (PMID: 16772608) (PMID: 12595854).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05291309392D          

 22 24  0  0  1  0            999 V2000
    2.3645    0.6188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -1.6952    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0070   -1.0032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2  9  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 12  2  0  0  0  0
 13 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1

> <INCHI_KEY>
GKTWGGQPFAXNFI-HNNXBMFYSA-N

> <FORMULA>
C16H16ClNO2S

> <MOLECULAR_WEIGHT>
321.822

> <EXACT_MASS>
321.059027158

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.1860321714566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
4.031763907999999

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.137540159712261

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
84.92699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clopidogrel

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAY-13         0                                  
HETATM    1 Cl   UNK     0       4.414   1.155   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      12.540  -3.164   0.000  0.00  0.00           S+0
HETATM    3  N   UNK     0       8.415  -1.155   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415  -2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748  -3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.540  -0.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.438  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -3.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -2.695   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   1.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.747   1.925   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.415   1.925   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.748   2.695   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       7.480  -1.873   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    9   12                                                       
CONECT    3    4    5    6                                                  
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    3   10   18   22                                             
CONECT    7    4    9                                                       
CONECT    8    5    9   11                                                  
CONECT    9    2    7    8                                                  
CONECT   10    6   13   14                                                  
CONECT   11    8   12                                                       
CONECT   12    2   11                                                       
CONECT   13    1   10   15                                                  
CONECT   14   10   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22    6                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(+)-Clopidogrel	ChEBI
Clopidogrelum	ChEBI
Plavix	Kegg
(+)-(S)-Clopidogrel	HMDB
(S)-Clopidogrel	HMDB
Clopidogrel bisulfate	HMDB
Clopidogrel bisulphate	HMDB
Isocover	HMDB
Clopidogrel sandoz	HMDB
Clopidogrel hydrochloride	HMDB
BMS Brand 1 OF clopidogrel bisulfate	HMDB
Clopidogrel napadisilate	HMDB
Clopidogrel, (+)(S)-isomer	HMDB
BMS Brand 2 OF clopidogrel bisulfate	HMDB
Clopidogrel besylate	HMDB
Iscover	HMDB
Clopidogrel-mepha	HMDB
Clopidogrel besilate	HMDB
Clopidogrel mepha	HMDB

Chemical Formula

C₁₆H₁₆ClNO₂S

Average Mass

321.8220 Da

Monoisotopic Mass

321.05903 Da

IUPAC Name

methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate

Traditional Name

clopidogrel

CAS Registry Number

Not Available

SMILES

[H][C@@](N1CCC2=C(C1)C=CS2)(C(=O)OC)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1

InChI Key

GKTWGGQPFAXNFI-HNNXBMFYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Thienopyridine
Chlorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Pyridine
Benzenoid
Heteroaromatic compound
Methyl ester
Thiophene
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl ester (CHEBI:37941 )
monochlorobenzenes (CHEBI:37941 )
thienopyridine (CHEBI:37941 )

Physical Properties

State

Not Available

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
logP	3.84	ALOGPS
logP	4.03	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	5.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.93 m³·mol⁻¹	ChemAxon
Polarizability	33.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005011

DrugBank ID

DB00758

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023584

KNApSAcK ID

Not Available

Chemspider ID

54632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clopidogrel

METLIN ID

3965

PubChem Compound

60606

PDB ID

Not Available

ChEBI ID

37941

Good Scents ID

Not Available

References

General References

Craft RM, Chavez JJ, Snider CC, Muenchen RA, Carroll RC: Comparison of modified Thrombelastograph and Plateletworks whole blood assays to optical platelet aggregation for monitoring reversal of clopidogrel inhibition in elective surgery patients. J Lab Clin Med. 2005 Jun;145(6):309-15. doi: 10.1016/j.lab.2005.03.010. [PubMed:15976759 ]
Chen YG, Xu F, Zhang Y, Ji QS, Sun Y, Lu RJ, Li RJ: Effect of aspirin plus clopidogrel on inflammatory markers in patients with non-ST-segment elevation acute coronary syndrome. Chin Med J (Engl). 2006 Jan 5;119(1):32-6. [PubMed:16454979 ]
Hulot JS, Bura A, Villard E, Azizi M, Remones V, Goyenvalle C, Aiach M, Lechat P, Gaussem P: Cytochrome P450 2C19 loss-of-function polymorphism is a major determinant of clopidogrel responsiveness in healthy subjects. Blood. 2006 Oct 1;108(7):2244-7. doi: 10.1182/blood-2006-04-013052. Epub 2006 Jun 13. [PubMed:16772608 ]
Gansera B, Schmidtler F, Spiliopoulos K, Angelis I, Neumaier-Prauser P, Kemkes BM: Urgent or emergent coronary revascularization using bilateral internal thoracic artery after previous clopidogrel antiplatelet therapy. Thorac Cardiovasc Surg. 2003 Aug;51(4):185-9. doi: 10.1055/s-2003-42260. [PubMed:14502454 ]
Bauriedel G, Skowasch D, Schneider M, Andrie R, Jabs A, Luderitz B: Antiplatelet effects of angiotensin-converting enzyme inhibitors compared with aspirin and clopidogrel: a pilot study with whole-blood aggregometry. Am Heart J. 2003 Feb;145(2):343-8. doi: 10.1067/mhj.2003.22. [PubMed:12595854 ]

Showing NP-Card for Clopidogrel (NP0334579)

MOL for NP0334579 (Clopidogrel)

3D MOL for NP0334579 (Clopidogrel)

3D SDF for NP0334579 (Clopidogrel)

3D-SDF for NP0334579 (Clopidogrel)

PDB for NP0334579 (Clopidogrel)

3D PDB for NP0334579 (Clopidogrel)

SMILES for NP0334579 (Clopidogrel)

INCHI for NP0334579 (Clopidogrel)

Structure for NP0334579 (Clopidogrel)

3D Structure for NP0334579 (Clopidogrel)