IMPPAT Phytochemical information: 
Codeine

Codeine
Summary

SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N
DeepSMILES: COcccccc6O[C@@H][C@]5CCN[C@H]C%11)[C@@H]6C=C[C@@H]%10O))))))C
Scaffold Graph/Node/Bond level: C1=CC2C3Cc4cccc5c4C2(CCN3)C(C1)O5
Scaffold Graph/Node level: C1CC2CC3NCCC45C(CCCC34)OC(C1)C25
Scaffold Graph level: C1CC2CC3CCCC45C(CCCC34)CC(C1)C25
Functional groups: cOC; CN(C)C; CC=CC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Morphinans
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Morphinan alkaloids
Synonymous chemical names:
(-) codeine, codeine, codein
External chemical identifiers:
CID:CID_5284371; ChEMBL:CHEMBL485; ChEBI:CHEBI:16714; ZINC:ZINC000003806721; FDASRS:UX6OWY2V7J; SureChEMBL:SCHEMBL3257
Chemical structure download


Codeine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 299.37
Log P RDKit 1.5
Topological polar surface area (Å2) RDKit 41.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Codeine
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 0.798144


Codeine
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 -7.32
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Codeine
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_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_000995ENSG00000101188NTSR14923ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_001001ENSG00000116329OPRD14985BindingDB, ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_001003ENSG00000112038OPRM14988BindingDB, ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000341ENSG00000136160EDNRB1910ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986BindingDB, ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000570ENSG00000288269GCGR2642ChEMBL
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000212ENSG00000106113CRHR21395ChEMBL
TAR_EXP_000211ENSG00000276191CRHR11394ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000579ENSG00000010310GIPR2696ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000520ENSG00000204681GABBR12550ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000739ENSG00000148680HTR73363ChEMBL
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001657ENSG00000171234UGT2B77364ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001538ENSG00000175003SLC22A16580BindingDB, ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001473ENSG00000183873SCN5A6331ChEMBL
TAR_EXP_001656ENSG00000156096UGT2B47363ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001451ENSG00000100739BDKRB1623ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS