IMPPAT Phytochemical information: 
(2S)-4-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one

(2S)-4-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one
Summary

SMILES: OCCc1c(C)c2c(c(c1C)O)C[C@@](C2=O)(C)CO
InChI: InChI=1S/C15H20O4/c1-8-10(4-5-16)9(2)13(18)11-6-15(3,7-17)14(19)12(8)11/h16-18H,4-7H2,1-3H3/t15-/m0/s1
InChIKey: DKTHZTCRZGYKCV-HNNXBMFYSA-N
DeepSMILES: OCCccC)cccc6C))O))C[C@@]C5=O))C)CO
Scaffold Graph/Node/Bond level: O=C1CCc2ccccc21
Scaffold Graph/Node level: OC1CCC2CCCCC12
Scaffold Graph level: CC1CCC2CCCCC12
Functional groups: CO; cO; cC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Indanes
ClassyFire Subclass: Indanones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Illudalane sesquiterpenoids
Synonymous chemical names:
onitisin
External chemical identifiers:
CID:CID_46849086; ZINC:ZINC000014618153; MolPort-035-706-175
Chemical structure download


(2S)-4-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.32
Log P RDKit 1.28
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


(2S)-4-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one
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 0.768273


(2S)-4-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-2,5,7-trimethyl-3H-inden-1-one
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 High
Log Kp (Skin permeation, cm/s) SwissADME -6.58
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes