IMPPAT Phytochemical information: 
Cannabisin D
Cannabisin D
Summary

SMILES: COc1cc2C=C(C(=O)NCCc3ccc(cc3)O)[C@H]([C@@H](c2cc1O)c1ccc(c(c1)OC)O)C(=O)NCCc1ccc(cc1)O
InChI: InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34-/m1/s1
InChIKey: XYTYRVFKBJENPE-KKLWWLSJSA-N
DeepSMILES: COcccC=CC=O)NCCcccccc6))O)))))))))[C@H][C@@H]c6cc%10O))))cccccc6)OC)))O))))))C=O)NCCcccccc6))O
Scaffold Graph/Node/Bond level: O=C(NCCc1ccccc1)C1=Cc2ccccc2C(c2ccccc2)C1C(=O)NCCc1ccccc1
Scaffold Graph/Node level: OC(NCCC1CCCCC1)C1CC2CCCCC2C(C2CCCCC2)C1C(O)NCCC1CCCCC1
Scaffold Graph level: CC(CCCC1CCCCC1)C1CC2CCCCC2C(C2CCCCC2)C1C(C)CCCC1CCCCC1
Functional groups: cOC; cO; CNC(C)=O; cC=C(C(=O)NC)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Aryltetralin lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
cannabisin d
External chemical identifiers:
CID:CID_44584134; ChEMBL:CHEMBL445592; ZINC:ZINC000044307185
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cannabisin D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 624.69
Log P RDKit 4.39
Topological polar surface area (Å2) RDKit 157.58
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 46
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 28
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.22
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Cannabisin D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.143496
Cannabisin D
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No