IMPPAT Phytochemical information: 
Repenone

Repenone
Summary

SMILES: COC(=O)OC1Oc2ccccc2-c2c1oc1cc(O)c(c(c1c2=O)O)O
InChI: InChI=1S/C18H12O9/c1-24-18(23)27-17-16-11(7-4-2-3-5-9(7)26-17)14(21)12-10(25-16)6-8(19)13(20)15(12)22/h2-6,17,19-20,22H,1H3
InChIKey: JHFAKPWBUSBCCY-UHFFFAOYSA-N
DeepSMILES: COC=O)OCOcccccc6-cc%10occcO)ccc6c%10=O)))O))O
Scaffold Graph/Node/Bond level: O=c1c2c(oc3ccccc13)COc1ccccc1-2
Scaffold Graph/Node level: OC1C2CCCCC2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCCCC2CC2CCC3CCCCC3C21
Functional groups: cOC(OC(=O)OC)c; coc; cO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Rotenoids
Synonymous chemical names:
repenone, Repenone
External chemical identifiers:
CID:CID_44257427
Chemical structure download


Repenone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.29
Log P RDKit 2.75
Topological polar surface area (Å2) RDKit 135.66
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 3
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


Repenone
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 0.434916


Repenone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.70
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No