IMPPAT Phytochemical information: 
Oripavine

Oripavine
Summary

SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O
InChI: InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
InChIKey: ZKLXUUYLEHCAMF-UUWFMWQGSA-N
DeepSMILES: COC=CC=C[C@][C@H]6Occ5cC[C@H]9NCC%11))C))))ccc6O
Scaffold Graph/Node/Bond level: C1=CC2Oc3cccc4c3C23CCNC(C4)C3=C1
Scaffold Graph/Node level: C1CC2CC3NCCC45C(CCCC34)OC(C1)C25
Scaffold Graph level: C1CC2CC3CCCC45C(CCCC34)CC(C1)C25
Functional groups: COC1=CC=C(C)CC1; cOC; CN(C)C; 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:
oripavine, Oripavine
External chemical identifiers:
CID:CID_5462306; ChEMBL:CHEMBL437602; ChEBI:CHEBI:7782; FDASRS:575AOU51CR; SureChEMBL:SCHEMBL37889
Chemical structure download


Oripavine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 297.35
Log P RDKit 2.12
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 3
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.44
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


Oripavine
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 0.861996


Oripavine
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 -6.79
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Oripavine
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_001003ENSG00000112038OPRM14988ChEMBL, NPASS