Secondary metabolite: 3α,15α,22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid



3α,15α,22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid
Summary
Molecular formula: C30H46O5
SMILES: O[C@@H](C([C@H]1C[C@@H]([C@@]2([C@]1(C)CC=C1C2=CCC2[C@]1(C)CC[C@H](C2(C)C)O)C)O)C)C/C=C(/C(=O)O)C
InChI: InChI=1S/C30H46O5/c1-17(26(34)35)8-10-22(31)18(2)21-16-25(33)30(7)20-9-11-23-27(3,4)24(32)13-14-28(23,5)19(20)12-15-29(21,30)6/h8-9,12,18,21-25,31-33H,10-11,13-16H2,1-7H3,(H,34,35)/b17-8+/t18?,21-,22-,23?,24-,25+,28-,29-,30-/m1/s1
InChIKey: VQYWTFJFAJFDIW-UVIHMKCZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3a,15a,22a-trihydroxylanosta-7,9(11),24-trien-26-oic acid, 3α,15α,22α-trihydroxylanosta-7,9(11),24-trien-26-oic acid
Chemical structure download



3α,15α,22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 486.69
Log P RDKit 5.26
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 30
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.77
Shape complexity RDKit 0.77
Number of rotatable bonds SwissADME 5
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



3α,15α,22α-Trihydroxylanosta-7,9(11),24-trien-26-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 3
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 0.4



3α,15α,22α-Trihydroxylanosta-7,9(11),24-trien-26-oic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.85
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 Yes
P-glycoprotein substrate SwissADME Yes




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