IMPPAT Phytochemical information: 
Cocaine
Cocaine
Summary

SMILES: COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
InChI: 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
InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-N
DeepSMILES: COC=O)[C@H][C@H]C[C@H]N[C@@H]6CC5)))C))))OC=O)cccccc6
Scaffold Graph/Node/Bond level: O=C(OC1CC2CCC(C1)N2)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCC(C1)N2)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCC(C2)C1)C1CCCCC1
Functional groups: CN(C)C; COC(C)=O; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzoic acids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Tropane alkaloids
Synonymous chemical names:
beta-cocaine, cocaine, corine
External chemical identifiers:
CID:446220; ChEMBL:CHEMBL370805; ChEBI:27958; ZINC:ZINC000003875336; FDASRS:I5Y540LHVR; SureChEMBL:SCHEMBL21930
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cocaine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Cocaine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7979
Cocaine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.52
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Cocaine
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000176183DRD4846
ENSP00000217305PDYN993
ENSP00000219833SLC6A2999
ENSP00000220809PLAT803
ENSP00000222982CYP3A5800
ENSP00000225245CCL3700
ENSP00000225831CCL2943
ENSP00000227163SPI1800
ENSP00000239938EGR1987
ENSP00000240874KALRN818
ENSP00000245323EFNB2817
ENSP00000245919FOSB962
ENSP00000249071RAC2704
ENSP00000254079PPP1R1B958
ENSP00000261707SLC6A4996
ENSP00000262186KCNH2929
ENSP00000263645CD81737
ENSP00000264381BCHE978
ENSP00000264426GRIA2718
ENSP00000264708POMC966
ENSP00000264832ICAM1800
ENSP00000265572OPRK1996
ENSP00000268164ST8SIA2800
ENSP00000269305TP53764
ENSP00000270162SIK1815
ENSP00000270349SLC6A3999
ENSP00000272190REN839
ENSP00000274026CCNA2833
ENSP00000279593868
ENSP00000282356CAMK4724
ENSP00000284292NRGN800
ENSP00000285900GRIA1943
ENSP00000292303CCR5824
ENSP00000293813853
ENSP00000295926CCNL1842
ENSP00000296777CARTPT937
ENSP00000297494NOS3930
ENSP00000298472SLC18A2953
ENSP00000299565CHRNA5855
ENSP00000301838FADD800
ENSP00000302150PRL776
ENSP00000303325TACR3725
ENSP00000304283RAC3704
ENSP00000305651CXCL10700
ENSP00000306138GRM5971
ENSP00000306245FOS993
ENSP00000306490CHRM1814
ENSP00000306512IL8938
ENSP00000307599SCN11A800
ENSP00000311032CASP3840
ENSP00000315477CD209822
ENSP00000316244HTR1A943
ENSP00000317842CES2843
ENSP00000318057EGR3705
ENSP00000319984CHRM2800
ENSP00000320295733
ENSP00000324173HSPA5824
ENSP00000324248PENK889
ENSP00000324806GSK3B786
ENSP00000328968SCN5A800
ENSP00000329623BCL2800
ENSP00000334382HOMER1862
ENSP00000337450CYP3A7800
ENSP00000337459NOS1804
ENSP00000337915CYP3A4962
ENSP00000337949HTR7900
ENSP00000338345SNCA879
ENSP00000341838TNNI3700
ENSP00000344468SDC3827
ENSP00000345096IMPDH1800
ENSP00000347754HTR3A904
ENSP00000348461RAC1704
ENSP00000353427NR4A1818
ENSP00000353720CES1816
ENSP00000353820CYP2D6824
ENSP00000354859DRD2976
ENSP00000358963HTR1B912
ENSP00000360608GRIN1981
ENSP00000364687EHMT2858
ENSP00000367959HTR2A996
ENSP00000368683EDN1846
ENSP00000370571TH995
ENSP00000376776DBH886
ENSP00000387699CREB1992
ENSP00000390600SCN10A800
ENSP00000393312FGFR1834
ENSP00000394624OPRM1991
ENSP00000395535MECP2864
ENSP00000397181RGS4840
ENSP00000398698TNF900
ENSP00000405963RASGRF1843
ENSP00000412237IL10700
ENSP00000414303BDNF977
ENSP00000428864CES5A800
ENSP00000430505IDO1830
ENSP00000451560TUBB3733
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.