IMPPAT Phytochemical information: 
Lupinisoflavone D

Lupinisoflavone D
Summary

SMILES: Oc1cc(O)c2c(c1)occ(c2=O)c1ccc2c(c1O)CC(O2)C(O)(C)C
InChI: InChI=1S/C20H18O7/c1-20(2,25)16-7-11-14(27-16)4-3-10(18(11)23)12-8-26-15-6-9(21)5-13(22)17(15)19(12)24/h3-6,8,16,21-23,25H,7H2,1-2H3
InChIKey: FEZXFNWSKGIOKM-UHFFFAOYSA-N
DeepSMILES: OcccO)ccc6)occc6=O))cccccc6O))CCO5)CO)C)C
Scaffold Graph/Node/Bond level: O=c1c(-c2ccc3c(c2)CCO3)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCC3OCCC3C2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCC2CCCC2C1
Functional groups: cO; coc; c=O; cOC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflav-2-enes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
lupinisoflavone d
External chemical identifiers:
CID:CID_5378771; ChEMBL:CHEMBL263445
Chemical structure download


Lupinisoflavone D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.36
Log P RDKit 2.65
Topological polar surface area (Å2) RDKit 120.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Lupinisoflavone D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.547182


Lupinisoflavone D
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No