IMPPAT Phytochemical information: 
Erythro-canabisine H
Erythro-canabisine H
Summary

SMILES: OC[C@@H]([C@H](c1ccc(c(c1)OC)O)O)Oc1ccc(cc1OC)/C=C/C(=O)NCCc1ccc(cc1)O
InChI: InChI=1S/C28H31NO8/c1-35-24-16-20(7-10-22(24)32)28(34)26(17-30)37-23-11-5-19(15-25(23)36-2)6-12-27(33)29-14-13-18-3-8-21(31)9-4-18/h3-12,15-16,26,28,30-32,34H,13-14,17H2,1-2H3,(H,29,33)/b12-6+/t26-,28-/m0/s1
InChIKey: PJAFJMNWVUKNOR-MGBVTPAKSA-N
DeepSMILES: OC[C@@H][C@H]cccccc6)OC)))O)))))O))Occcccc6OC))))/C=C/C=O)NCCcccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccc(OCCc2ccccc2)cc1)NCCc1ccccc1
Scaffold Graph/Node level: OC(CCC1CCC(OCCC2CCCCC2)CC1)NCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)CCC1CCC(CCCC2CCCCC2)CC1
Functional groups: CO; cO; cOC; c/C=C/C(=O)NC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenylpropanoids (C6-C3)|Lignans
NP Classifier Class: Cinnamic acid amides|Neolignans
Synonymous chemical names:
erythro-canabisine h
External chemical identifiers:
CID:CID_636543; ZINC:ZINC000013383040; MolPort-039-338-454
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Erythro-canabisine H
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 509.56
Log P RDKit 2.96
Topological polar surface area (Å2) RDKit 137.71
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 12
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Erythro-canabisine H
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.24
Erythro-canabisine H
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.80
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes