Secondary metabolite: 3b,7b-Dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester



3b,7b-Dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester
Summary
Molecular formula: C33H46O9
SMILES: COC(=O)C(CC(=O)C[C@H](C1=CC(=O)[C@@]2([C@]1(C)[C@H](OC(=O)C)C(=O)C1=C2[C@@H](O)CC2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)C
InChI: InChI=1S/C33H46O9/c1-16(12-19(35)13-17(2)29(40)41-9)20-14-24(38)33(8)25-21(36)15-22-30(4,5)23(37)10-11-31(22,6)26(25)27(39)28(32(20,33)7)42-18(3)34/h14,16-17,21-23,28,36-37H,10-13,15H2,1-9H3/t16-,17?,21+,22?,23+,28-,31+,32+,33+/m1/s1
InChIKey: GQKGKJKALUUAHP-NNTVZRGMSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3b,7b-dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester
Chemical structure download



3b,7b-Dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 586.72
Log P RDKit 3.68
Topological polar surface area (Å2) RDKit 144.27
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 24
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.73
Shape complexity RDKit 0.73
Number of rotatable bonds SwissADME 9
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



3b,7b-Dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester
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 0.43



3b,7b-Dihydroxy-12b-acetoxy-11,15,23-trioxo-5 a -lanosta-8-en-26-oic acid methyl ester
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -8.32
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 No




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