IMPPAT Phytochemical information: 
Gambiriin B3
Gambiriin B3
Summary

SMILES: Oc1cc(O)c(c(c1)O)C[C@H]1Oc2c([C@H]1c1ccc(c(c1)O)O)c(O)c1c(c2)O[C@@H]([C@H](C1)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C30H26O11/c31-14-7-19(34)15(20(35)8-14)10-25-27(12-1-3-17(32)21(36)5-12)28-26(40-25)11-24-16(29(28)39)9-23(38)30(41-24)13-2-4-18(33)22(37)6-13/h1-8,11,23,25,27,30-39H,9-10H2/t23-,25+,27-,30+/m0/s1
InChIKey: FFCVTFZKQFEUKL-YJRUHBOJSA-N
DeepSMILES: OcccO)ccc6)O))C[C@H]Occ[C@H]5cccccc6)O))O))))))cO)ccc6)O[C@@H][C@H]C6)O))cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccc(CC2Oc3cc4c(cc3C2c2ccccc2)CCC(c2ccccc2)O4)cc1
Scaffold Graph/Node level: C1CCC(CC2OC3CC4OC(C5CCCCC5)CCC4CC3C2C2CCCCC2)CC1
Scaffold Graph level: C1CCC(CC2CC3CC4CC(C5CCCCC5)CCC4CC3C2C2CCCCC2)CC1
Functional groups: cO; CO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavan-3-ols|Proanthocyanins
Synonymous chemical names:
gambiriin b3, Gambiriin B3
External chemical identifiers:
CID:CID_46173996; ChEBI:CHEBI:81330; ZINC:ZINC000056874794
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gambiriin B3
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.53
Log P RDKit 3.5
Topological polar surface area (Å2) RDKit 200.53
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
Gambiriin B3
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
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 0.16486
Gambiriin B3
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.26
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No