IMPPAT Phytochemical information: 
(1R,2S)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-1,2-dihydronaphthalene-2,3-dicarboxamide
(1R,2S)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-1,2-dihydronaphthalene-2,3-dicarboxamide
Summary

SMILES: Oc1ccc(cc1)CCNC(=O)C1=Cc2cc(O)c(cc2[C@H]([C@@H]1C(=O)NCCc1ccc(cc1)O)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C34H32N2O8/c37-23-6-1-19(2-7-23)11-13-35-33(43)26-15-22-17-29(41)30(42)18-25(22)31(21-5-10-27(39)28(40)16-21)32(26)34(44)36-14-12-20-3-8-24(38)9-4-20/h1-10,15-18,31-32,37-42H,11-14H2,(H,35,43)(H,36,44)/t31-,32-/m1/s1
InChIKey: XENYXHLAFMZULS-ROJLCIKYSA-N
DeepSMILES: Occcccc6))CCNC=O)C=CcccO)ccc6[C@H][C@@H]%10C=O)NCCcccccc6))O))))))))))cccccc6)O))O))))))))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: cO; cC=C(C(=O)NC)C; CNC(C)=O
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 b
External chemical identifiers:
CID:CID_101631692; ZINC:ZINC000085881446
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2S)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-1,2-dihydronaphthalene-2,3-dicarboxamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 596.64
Log P RDKit 3.78
Topological polar surface area (Å2) RDKit 179.58
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 44
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 6
Shape complexity RDKit 0.18
Number of rotatable bonds RDKit 9
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
(1R,2S)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-1,2-dihydronaphthalene-2,3-dicarboxamide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.13
(1R,2S)-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-1,2-dihydronaphthalene-2,3-dicarboxamide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately 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 -6.94
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No