Secondary metabolite: 2-(3-Carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone



2-(3-Carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone
Summary
Molecular formula: C10H14O4
SMILES: OC(=O)CC(CC1=C(C)CCC1=O)O
InChI: InChI=1S/C10H14O4/c1-6-2-3-9(12)8(6)4-7(11)5-10(13)14/h7,11H,2-5H2,1H3,(H,13,14)
InChIKey: KHOGFVBKFSKLTN-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Hydroxy acids and derivatives
Sub class: Beta hydroxy acids and derivatives
Synonymous chemical names:
2-(3-carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone
Chemical structure download



2-(3-Carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 198.22
Log P RDKit 0.89
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 14
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 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 6
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.6
Shape complexity RDKit 0.6
Number of rotatable bonds SwissADME 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1



2-(3-Carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone
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
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7



2-(3-Carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.79
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 No




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo