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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (14)transporters (3) Show 17 proteins XML

enzymes (14)transporters (3) Show 17 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 02:51:50 UTC

HMDB ID

HMDB0015043

Secondary Accession Numbers

HMDB15043

Metabolite Identification

Common Name

Cocaine

Description

Cocaine, also known as coke, is an alkaloid ester obtained from the leaves of the coca plant (PMID: 20857618 ). It is a weakly alkaline compound and can therefore combine with acidic compounds to form white salts or powders (which is how it is typically sold and consumed). Cocaine is a strong stimulant that is most frequently used as a recreational drug. It is the second most frequently used illegal drug globally, after cannabis. The stimulant and hunger suppression properties of cocaine and coca leaf extracts have been known for thousands of years by indigenous groups in central and South America. The coca leaf was, and still is, chewed almost universally by some indigenous communities. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This inhibition leads to a number of mental and physical effects that may include loss of contact with reality, an intense feeling of happiness, periods of agitation, along with a rapid heart rate, sweating, and dialated pupils. Cocaine is highly addictive due to its effect on the reward pathway in the brain (PMID: 22856655 ). Cocaine addiction occurs through overexpression of the FosB protein in the nucleus accumbens of the brain, which results in altered transcriptional regulation in neurons within the nucleus accumbens. Cocaine is harmful. Its use increases the risk of stroke, myocardial infarction, lung problems (in those who smoke it), blood infections, and sudden cardiac death. Medically, cocaine is infrequently used as a local anesthetic and vasoconstrictor to cause loss of feeling or numbness before certain medical procedures (e.g., biopsy, stitches, wound cleaning) (PMID: 28956316 ). Topical cocaine is occasionally used as a local numbing agent to help with painful procedures in the mouth or nose. Cocaine is now predominantly used for nasal and lacrimal duct surgery. It works quickly to numb certain areas of the body (e.g., nose, ear, or throat) about 1-2 minutes after application. Cocaine functions as an anesthesia by reversibly binding to and inactivating sodium channels, thereby inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. Cocaine and its major metabolites are only found in individuals that have used or taken this drug.

Structure

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

HMDB0015043
     RDKit          3D
Cocaine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2101    3.5983   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    2.2905   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.4252   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820    1.8819    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.0632   -0.8218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4252   -0.7078   -1.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6635   -0.2210   -0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.2710   -0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.2846   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    0.7951   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0401    1.2861   -0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1453    1.7802   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551    1.7859    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    1.2972    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580    0.8049    1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.1805   -0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434   -2.5306    0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8753   -2.7791   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -1.4440   -0.4339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -0.5438    0.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7474   -1.3635    1.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524   -1.6609    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794    3.6668    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    4.2925   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    3.8892   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    0.1517   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752   -0.5971   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0137    1.2733   -2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    2.1600   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0113    2.1687    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    1.2983    2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    0.4277    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -2.7485   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466   -2.6010   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -3.4212    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -3.0655   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -3.5816    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919   -1.0622   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117   -1.5577    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276    0.2429    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.5908    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -1.6874    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.7908    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  6 27  1  6
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  1
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END


  Mrv0541 04191212152D          

 24 26  0  0  0  0            999 V2000
   -0.6312    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5245    1.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    0.5897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.9507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9620    1.5927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6765    2.8302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765    2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3910    1.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1055    2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    2.7757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    4.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957    3.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102    2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9247    1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    1.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9247    3.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2102    1.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456    0.7885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9425    0.5750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081    0.7885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5050    0.5750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  3  6  1  0  0  0  0
  7 21  1  0  0  0  0
 21  1  1  0  0  0  0
  1  2  1  0  0  0  0
  2 23  1  0  0  0  0
 23  3  1  0  0  0  0
 21  4  1  1  0  0  0
 23  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6 12  1  1  0  0  0
  7  9  1  1  0  0  0
  9  8  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 14 13  2  0  0  0  0
 14 15  1  0  0  0  0
 19 15  2  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 20 16  2  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  1  0  0  0
 23 24  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0015043

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
ZPUCINDJVBIVPJ-LJISPDSOSA-N

> <FORMULA>
C17H21NO4

> <MOLECULAR_WEIGHT>
303.3529

> <EXACT_MASS>
303.147058165

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.36274815445442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.2821080089999994

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.845774190899235

> <JCHEM_POLAR_SURFACE_AREA>
55.84

> <JCHEM_REFRACTIVITY>
81.16040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cocaine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015043
     RDKit          3D
Cocaine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2101    3.5983   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    2.2905   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.4252   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820    1.8819    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.0632   -0.8218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4252   -0.7078   -1.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6635   -0.2210   -0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.2710   -0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.2846   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    0.7951   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0401    1.2861   -0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1453    1.7802   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551    1.7859    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    1.2972    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580    0.8049    1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.1805   -0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434   -2.5306    0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8753   -2.7791   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -1.4440   -0.4339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -0.5438    0.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7474   -1.3635    1.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524   -1.6609    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794    3.6668    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    4.2925   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    3.8892   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    0.1517   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752   -0.5971   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0137    1.2733   -2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    2.1600   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0113    2.1687    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    1.2983    2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    0.4277    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -2.7485   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466   -2.6010   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -3.4212    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -3.0655   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -3.5816    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919   -1.0622   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117   -1.5577    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276    0.2429    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.5908    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -1.6874    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.7908    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  6 27  1  6
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  1
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.178   0.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.362   0.268   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.979   2.973   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -0.420   1.101   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.420   2.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.408   3.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.796   2.973   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.129   5.283   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.129   3.743   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.463   2.973   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.797   3.743   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.408   5.181   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.925   7.491   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.925   5.951   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.259   5.181   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.593   2.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.926   3.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.926   5.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.593   5.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.259   3.641   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.138   1.472   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      -3.626   1.073   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       1.322   1.472   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       2.809   1.073   0.000  0.00  0.00           H+0
CONECT    1   21    2                                                       
CONECT    2    1   23                                                       
CONECT    3    6   23                                                       
CONECT    4   21   23    5                                                  
CONECT    5    4                                                            
CONECT    6    7    3   12                                                  
CONECT    7    6   21    9                                                  
CONECT    8    9                                                            
CONECT    9    7    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6   14                                                       
CONECT   13   14                                                            
CONECT   14   12   13   15                                                  
CONECT   15   14   19   20                                                  
CONECT   16   17   20                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18                                                       
CONECT   20   15   16                                                       
CONECT   21    7    1    4   22                                             
CONECT   22   21                                                            
CONECT   23    2    3    4   24                                             
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015043
HETATM    1  C1  UNL     1      -0.210   3.598  -0.646  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.547   2.290  -1.128  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.321   1.425  -0.348  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.682   1.882   0.774  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.685   0.063  -0.822  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.425  -0.708  -1.064  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.663  -0.221  -0.316  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.767   0.271  -0.991  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.800   0.285  -2.266  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.939   0.795  -0.315  1.00  0.00           C  
HETATM   11  C7  UNL     1       4.040   1.286  -0.979  1.00  0.00           C  
HETATM   12  C8  UNL     1       5.145   1.780  -0.315  1.00  0.00           C  
HETATM   13  C9  UNL     1       5.155   1.786   1.063  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.059   1.297   1.742  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.958   0.805   1.055  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.542  -2.180  -0.793  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.543  -2.531   0.256  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.875  -2.779  -0.445  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.568  -1.444  -0.434  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.575  -0.544   0.229  1.00  0.00           C  
HETATM   21  N1  UNL     1      -1.747  -1.363   1.084  1.00  0.00           N  
HETATM   22  C17 UNL     1      -2.352  -1.661   2.351  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.379   3.667   0.447  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.905   4.293  -1.191  1.00  0.00           H  
HETATM   25  H3  UNL     1       0.806   3.889  -0.953  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.295   0.152  -1.748  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.175  -0.597  -2.136  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.014   1.273  -2.064  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.997   2.160  -0.831  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.011   2.169   1.632  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.059   1.298   2.826  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.112   0.428   1.587  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.803  -2.749  -1.720  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.447  -2.601  -0.462  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.248  -3.421   0.828  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.725  -3.065  -1.508  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.440  -3.582   0.046  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.792  -1.062  -1.458  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.512  -1.558   0.138  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.128   0.243   0.787  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.955  -2.591   2.350  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.543  -1.687   3.113  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.998  -0.791   2.624  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   20   26
CONECT    6    7   16   27
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   32
CONECT   16   17   33   34
CONECT   17   18   21   35
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   21   40
CONECT   21   22
CONECT   22   41   42   43
END

HMDB0015043
     RDKit          3D
Cocaine
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2101    3.5983   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5467    2.2905   -1.1280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.4252   -0.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820    1.8819    0.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6854    0.0632   -0.8218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4252   -0.7078   -1.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6635   -0.2210   -0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.2710   -0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    0.2846   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9390    0.7951   -0.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0401    1.2861   -0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1453    1.7802   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551    1.7859    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    1.2972    1.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580    0.8049    1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5423   -2.1805   -0.7929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5434   -2.5306    0.2559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8753   -2.7791   -0.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682   -1.4440   -0.4339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -0.5438    0.2293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7474   -1.3635    1.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524   -1.6609    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794    3.6668    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9046    4.2925   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058    3.8892   -0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2954    0.1517   -1.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1752   -0.5971   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0137    1.2733   -2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969    2.1600   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0113    2.1687    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0593    1.2983    2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1121    0.4277    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -2.7485   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4466   -2.6010   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2485   -3.4212    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -3.0655   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -3.5816    0.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919   -1.0622   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5117   -1.5577    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276    0.2429    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.5908    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -1.6874    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979   -0.7908    2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  6 27  1  6
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  1
 22 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Cocaine	ChEBI
2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester)	ChEBI
[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester	ChEBI
Benzoylmethylecgonine	ChEBI
beta-Cocain	ChEBI
Cocain	ChEBI
Cocaina	ChEBI
Cocainum	ChEBI
Kokain	ChEBI
L-Cocain	ChEBI
L-Cocaine	ChEBI
Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	ChEBI
Methyl benzoylecgonine	ChEBI
Neurocaine	ChEBI
2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylate benzoate (ester)	Generator
2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylic acid benzoic acid (ester)	Generator
2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylic acid benzoic acid (ester)	Generator
2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylate benzoate (ester)	Generator
2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylic acid benzoic acid (ester)	Generator
[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, methyl ester	Generator
b-Cocain	Generator
Β-cocain	Generator
Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	Generator
(−)-cocaine	HMDB
Cocaine HCL	HMDB
Hydrochloride, cocaine	HMDB
Cocaine hydrochloride	HMDB
HCL, Cocaine	HMDB

Chemical Formula

C₁₇H₂₁NO₄

Average Molecular Weight

303.3529

Monoisotopic Molecular Weight

303.147058165

IUPAC Name

methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

cocaine

CAS Registry Number

50-36-2

SMILES

[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C

InChI Identifier

InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1

InChI Key

ZPUCINDJVBIVPJ-LJISPDSOSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Methyl ester
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:27958 )
tropane alkaloid (CHEBI:27958 )
methyl ester (CHEBI:27958 )
benzoate ester (CHEBI:27958 )
Tropane alkaloids (C01416 )
Alkaloids (C01416 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.03 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	169.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.03 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.28	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	32.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.54	31661259
DarkChem	[M-H]-	165.46	31661259
DeepCCS	[M-2H]-	204.701	30932474
DeepCCS	[M+Na]+	179.21	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.4	32859911
AllCCS	[M-H]-	173.4	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	173.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cocaine	[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C	3168.9	Standard polar	33892256
Cocaine	[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C	2330.9	Standard non polar	33892256
Cocaine	[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(=O)OC)N2C	2215.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cocaine EI-B (Non-derivatized)	splash10-001i-9200000000-5262d40bbcdec08759ab	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cocaine CI-B (Non-derivatized)	splash10-0udi-0109000000-319d789d066a157a0966	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cocaine EI-B (Non-derivatized)	splash10-001i-9200000000-5262d40bbcdec08759ab	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Cocaine CI-B (Non-derivatized)	splash10-0udi-0109000000-319d789d066a157a0966	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5a-9620000000-fd84236e0a4ca8f55456	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cocaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-a2004e33ce1140fd0ed1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-QTOF , positive-QTOF	splash10-0f89-0908000000-b5abe87da56f09f21f65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-ee9c7f3b491476f49e98	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-2dab4b98f61ec4ba2467	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-QTOF , positive-QTOF	splash10-0fz9-0900000000-b3c61e257fbaf700b52b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-3b1dc1a8c8390bfb6c3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-0479d3211208134ed140	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0ue9-0709000000-d19680d406708cbbc59b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-1900000000-5ac8f8a2719f70332b86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-3900000000-5ff2f6c28b5db03035be	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-053r-8900000000-e597f9f6f5014d501e62	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0a5c-9500000000-0fcf099229f148719078	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0udi-0009000000-ee11934dd1158606bb84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0ue9-0609000000-bd90cd1f98ce1845ba6b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-1900000000-9fc49ca16ab794b8c37d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-3900000000-cb0b593e7f379f7c6aef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-053r-8900000000-2a88bad614aed29eac52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-0a59-9500000000-c9713abdcf52a45d6ed2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cocaine LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-c18cf276038cf1946f20	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 10V, Positive-QTOF	splash10-0udi-0859000000-d8747974615dabc86511	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 20V, Positive-QTOF	splash10-0ac0-0921000000-20e84a94ac21e65e27c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 40V, Positive-QTOF	splash10-0a4i-4900000000-1e0f166133422838c089	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 10V, Negative-QTOF	splash10-0udi-0319000000-e9a39c150cc22fe3585e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 20V, Negative-QTOF	splash10-0umi-4955000000-dea1abe1f68405b6dcd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cocaine 40V, Negative-QTOF	splash10-0fi9-3900000000-c6cb0f24abf4c5d1446d	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cocaine 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 DB00907	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00907	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00907

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Cocaine

METLIN ID

Not Available

PubChem Compound

446220

PDB ID

COC

ChEBI ID

27958

Food Biomarker Ontology

Not Available

VMH ID

COKE

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. [PubMed:3940302 ]
Volkow ND, Wang GJ, Fischman MW, Foltin R, Fowler JS, Franceschi D, Franceschi M, Logan J, Gatley SJ, Wong C, Ding YS, Hitzemann R, Pappas N: Effects of route of administration on cocaine induced dopamine transporter blockade in the human brain. Life Sci. 2000 Aug 11;67(12):1507-15. [PubMed:10983846 ]
Uz T, Akhisaroglu M, Ahmed R, Manev H: The pineal gland is critical for circadian Period1 expression in the striatum and for circadian cocaine sensitization in mice. Neuropsychopharmacology. 2003 Dec;28(12):2117-23. [PubMed:12865893 ]
Dimitrijevic N, Dzitoyeva S, Manev H: An automated assay of the behavioral effects of cocaine injections in adult Drosophila. J Neurosci Methods. 2004 Aug 30;137(2):181-4. [PubMed:15262059 ]
McClung CA, Sidiropoulou K, Vitaterna M, Takahashi JS, White FJ, Cooper DC, Nestler EJ: Regulation of dopaminergic transmission and cocaine reward by the Clock gene. Proc Natl Acad Sci U S A. 2005 Jun 28;102(26):9377-81. Epub 2005 Jun 20. [PubMed:15967985 ]
Lippi G, Plebani M, Cervellin G: Cocaine in acute myocardial infarction. Adv Clin Chem. 2010;51:53-70. doi: 10.1016/s0065-2423(10)51003-5. [PubMed:20857618 ]
Pomara C, Cassano T, D'Errico S, Bello S, Romano AD, Riezzo I, Serviddio G: Data available on the extent of cocaine use and dependence: biochemistry, pharmacologic effects and global burden of disease of cocaine abusers. Curr Med Chem. 2012;19(33):5647-57. doi: 10.2174/092986712803988811. [PubMed:22856655 ]
Beaulieu P: Anesthetic implications of recreational drug use. Can J Anaesth. 2017 Dec;64(12):1236-1264. doi: 10.1007/s12630-017-0975-0. Epub 2017 Sep 27. [PubMed:28956316 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Cocaine + Water → Ecgonine methyl ester + Benzoic acid	details

Enzyme Details

2. Cocaine esterase

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:: CES2
Uniprot ID:: O00748
Molecular weight:: 68898.39

Reactions

Cocaine + Water → Ecgonine methyl ester + Benzoic acid	details

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Ladona MG, Gonzalez ML, Rane A, Peter RM, de la Torre R: Cocaine metabolism in human fetal and adult liver microsomes is related to cytochrome P450 3A expression. Life Sci. 2000 Dec 15;68(4):431-43. [PubMed:11205892 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

7. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

8. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Wilson JM, Levey AI, Bergeron C, Kalasinsky K, Ang L, Peretti F, Adams VI, Smialek J, Anderson WR, Shannak K, Deck J, Niznik HB, Kish SJ: Striatal dopamine, dopamine transporter, and vesicular monoamine transporter in chronic cocaine users. Ann Neurol. 1996 Sep;40(3):428-39. [PubMed:8797532 ]
Kim DI, Schweri MM, Deutsch HM: Synthesis and pharmacology of site specific cocaine abuse treatment agents: 8-substituted isotropane (3-azabicyclo[3.2.1]octane) dopamine uptake inhibitors. J Med Chem. 2003 Apr 10;46(8):1456-64. [PubMed:12672245 ]
Rothman RB, Baumann MH, Dersch CM, Appel J, Houghten RA: Discovery of novel peptidic dopamine transporter ligands by screening a positional scanning combinatorial hexapeptide library. Synapse. 1999 Sep 1;33(3):239-46. [PubMed:10420171 ]
Carrera MR, Meijler MM, Janda KD: Cocaine pharmacology and current pharmacotherapies for its abuse. Bioorg Med Chem. 2004 Oct 1;12(19):5019-30. [PubMed:15351386 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

10. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Antzelevitch C: Brugada syndrome. Pacing Clin Electrophysiol. 2006 Oct;29(10):1130-59. [PubMed:17038146 ]
Satish OS, Yeh KH, Wen MS: Brugada syndrome--an update. Chang Gung Med J. 2005 Feb;28(2):69-76. [PubMed:15880981 ]
Wright SN, Wang SY, Xiao YF, Wang GK: State-dependent cocaine block of sodium channel isoforms, chimeras, and channels coexpressed with the beta1 subunit. Biophys J. 1999 Jan;76(1 Pt 1):233-45. [PubMed:9876137 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Galli A, DeFelice LJ, Duke BJ, Moore KR, Blakely RD: Sodium-dependent norepinephrine-induced currents in norepinephrine-transporter-transfected HEK-293 cells blocked by cocaine and antidepressants. J Exp Biol. 1995 Oct;198(Pt 10):2197-212. [PubMed:7500004 ]
Burchett SA, Bannon MJ: Serotonin, dopamine and norepinephrine transporter mRNAs: heterogeneity of distribution and response to 'binge' cocaine administration. Brain Res Mol Brain Res. 1997 Oct 3;49(1-2):95-102. [PubMed:9387868 ]
Zhao Y, Sun L: Perinatal cocaine exposure reduces myocardial norepinephrine transporter function in the neonatal rat. Neurotoxicol Teratol. 2004 May-Jun;26(3):443-50. [PubMed:15113605 ]
Carrera MR, Meijler MM, Janda KD: Cocaine pharmacology and current pharmacotherapies for its abuse. Bioorg Med Chem. 2004 Oct 1;12(19):5019-30. [PubMed:15351386 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Patkar AA, Berrettini WH, Hoehe M, Thornton CC, Gottheil E, Hill K, Weinstein SP: Serotonin transporter polymorphisms and measures of impulsivity, aggression, and sensation seeking among African-American cocaine-dependent individuals. Psychiatry Res. 2002 Jun 1;110(2):103-15. [PubMed:12057823 ]
Barker EL, Moore KR, Rakhshan F, Blakely RD: Transmembrane domain I contributes to the permeation pathway for serotonin and ions in the serotonin transporter. J Neurosci. 1999 Jun 15;19(12):4705-17. [PubMed:10366604 ]
Corey JL, Quick MW, Davidson N, Lester HA, Guastella J: A cocaine-sensitive Drosophila serotonin transporter: cloning, expression, and electrophysiological characterization. Proc Natl Acad Sci U S A. 1994 Feb 1;91(3):1188-92. [PubMed:8302852 ]
Carrera MR, Meijler MM, Janda KD: Cocaine pharmacology and current pharmacotherapies for its abuse. Bioorg Med Chem. 2004 Oct 1;12(19):5019-30. [PubMed:15351386 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

3. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Cocaine (HMDB0015043)

MOL for HMDB0015043 (Cocaine)

3D MOL for HMDB0015043 (Cocaine)

3D SDF for HMDB0015043 (Cocaine)

3D-SDF for HMDB0015043 (Cocaine)

PDB for HMDB0015043 (Cocaine)

3D PDB for HMDB0015043 (Cocaine)

SMILES for HMDB0015043 (Cocaine)

INCHI for HMDB0015043 (Cocaine)

Structure for HMDB0015043 (Cocaine)

3D Structure for HMDB0015043 (Cocaine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

References

References

References

References

References

References

Transporters

References

References

References