Secondary metabolite: 15α-Hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid



15α-Hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid
Summary
Molecular formula: C31H46O4
SMILES: CC(C(=C)CC[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC=C1C2=CCC2[C@]1(C)CCC(=O)C2(C)C)C)O)C(=O)O)C
InChI: InChI=1S/C31H46O4/c1-18(2)19(3)9-10-20(27(34)35)23-17-26(33)31(8)22-11-12-24-28(4,5)25(32)14-15-29(24,6)21(22)13-16-30(23,31)7/h11,13,18,20,23-24,26,33H,3,9-10,12,14-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24?,26+,29-,30-,31-/m1/s1
InChIKey: OSACBIMFKXGCAD-MXOXIGHFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Bile acids, alcohols and derivatives
Synonymous chemical names:
15α-hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid, 3–keto–dehydrosulfurenic acid
Chemical structure download



15α-Hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 482.7
Log P RDKit 6.74
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 31
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.74
Shape complexity RDKit 0.74
Number of rotatable bonds SwissADME 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



15α-Hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41



15α-Hydroxy-3-oxo-24-methylenelanosta-7,9(11)-dien-21-oic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.96
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




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