Secondary metabolite: 3α,5α,8β-Trihydroxycleistanth-13(17),15-dien-18-oic acid



3α,5α,8β-Trihydroxycleistanth-13(17),15-dien-18-oic acid
Summary
Molecular formula: C20H30O5
SMILES: C=C[C@@H]1C(=C)CC[C@H]2[C@@]1(O)CC[C@@]1([C@]2(C)CC[C@H]([C@@]1(C)C(=O)O)O)O
InChI: InChI=1S/C20H30O5/c1-5-13-12(2)6-7-14-17(3)9-8-15(21)18(4,16(22)23)20(17,25)11-10-19(13,14)24/h5,13-15,21,24-25H,1-2,6-11H2,3-4H3,(H,22,23)/t13-,14-,15-,17-,18+,19-,20+/m1/s1
InChIKey: MECXSJIILFRSID-XSINAMBDSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Steroid acids
Synonymous chemical names:
3α,5α,8β-trihydroxycleistanth-13(17),15-dien-18-oic acid
Chemical structure download



3α,5α,8β-Trihydroxycleistanth-13(17),15-dien-18-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 350.45
Log P RDKit 2.26
Topological polar surface area (Å2) RDKit 97.99
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.75
Shape complexity RDKit 0.75
Number of rotatable bonds SwissADME 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



3α,5α,8β-Trihydroxycleistanth-13(17),15-dien-18-oic acid
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’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.57



3α,5α,8β-Trihydroxycleistanth-13(17),15-dien-18-oic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 1
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




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