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: COC(C)=O; CN(C)C; 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:CID_446220; ChEMBL:CHEMBL370805; ChEBI: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 303.36
Log P RDKit 1.87
Topological polar surface area (Å2) RDKit 55.84
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
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 0.797936
Cocaine
ADME 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 - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL, NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000065ENSG00000198848CES11066ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813BindingDB, ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000526ENSG00000145863GABRA62559NPASS
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531BindingDB, ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530BindingDB, ChEMBL, NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532BindingDB, ChEMBL, NPASS