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

SMILES: Oc1ccc(cc1)CCNC(=O)c1cc2cc(O)c(cc2c(c1C(=O)NCCc1ccc(cc1)O)c1ccc(c(c1)O)O)O
InChI: InChI=1S/C34H30N2O8/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/h1-10,15-18,37-42H,11-14H2,(H,35,43)(H,36,44)
InChIKey: CLNINZAIEQRASP-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCNC=O)cccccO)ccc6cc%10C=O)NCCcccccc6))O))))))))))cccccc6)O))O))))))))O
Scaffold Graph/Node/Bond level: O=C(NCCc1ccccc1)c1cc2ccccc2c(-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(=O)NC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Arylnaphthalene lignans
Synonymous chemical names:
cannabisin a
External chemical identifiers:
CID:CID_15086398; ZINC:ZINC000085881442; MolPort-047-581-914
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]naphthalene-2,3-dicarboxamide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 594.62
Log P RDKit 4.69
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 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 30
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 5
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 5
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
1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]naphthalene-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 0.11
1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]naphthalene-2,3-dicarboxamide
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 -6.28
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No