IMPPAT Phytochemical information: 
Repenol

Repenol
Summary

SMILES: COC(=O)OC1Oc2cc(O)ccc2-c2c1oc1cc(O)c(c(c1c2=O)O)O
InChI: InChI=1S/C18H12O10/c1-25-18(24)28-17-16-11(7-3-2-6(19)4-9(7)27-17)14(22)12-10(26-16)5-8(20)13(21)15(12)23/h2-5,17,19-21,23H,1H3
InChIKey: MQAHKRVNVQQRHE-UHFFFAOYSA-N
DeepSMILES: COC=O)OCOcccO)ccc6-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; cO; coc; 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:
Repenol, repenol
External chemical identifiers:
CID:CID_44257428
Chemical structure download


Repenol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 388.28
Log P RDKit 2.46
Topological polar surface area (Å2) RDKit 155.89
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 10
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


Repenol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36


Repenol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.04
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 No
P-glycoprotein substrate SwissADME No