Secondary metabolite: 15α-Acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol



15α-Acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol
Summary
Molecular formula: C32H50O4
SMILES: OC/C(=C/CC[C@H]([C@H]1C[C@@H]([C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)OC(=O)C)C)/C
InChI: InChI=1S/C32H50O4/c1-20(19-33)10-9-11-21(2)25-18-28(36-22(3)34)32(8)24-12-13-26-29(4,5)27(35)15-16-30(26,6)23(24)14-17-31(25,32)7/h10,12,14,21,25-28,33,35H,9,11,13,15-19H2,1-8H3/b20-10+/t21-,25-,26+,27+,28+,30-,31-,32-/m1/s1
InChIKey: OCXPPHJZMMXOOC-CAQVYMNZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
15α-acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol
Chemical structure download



15α-Acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.75
Log P RDKit 6.77
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 25
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.78
Shape complexity RDKit 0.78
Number of rotatable bonds SwissADME 7
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-Acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol
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 0.31



15α-Acetoxy-5α-lanosta-7,9(11),24-trien-3β,26-diol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -4.66
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 No




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