Secondary metabolite: 12b-Acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-26-oic acid



12b-Acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-26-oic acid
Summary
Molecular formula: C32H44O9
SMILES: O=C(CC(C1=CC(=O)[C@@]2([C@]1(C)[C@H](OC(=O)C)C(=O)C1=C2[C@@H](O)C[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)CC(C(=O)O)C
InChI: InChI=1S/C32H44O9/c1-15(11-18(34)12-16(2)28(39)40)19-13-23(37)32(8)24-20(35)14-21-29(4,5)22(36)9-10-30(21,6)25(24)26(38)27(31(19,32)7)41-17(3)33/h13,15-16,20-22,27,35-36H,9-12,14H2,1-8H3,(H,39,40)/t15?,16?,20-,21-,22-,27+,30-,31-,32-/m0/s1
InChIKey: RCSUYODNPCNTDX-SHFWFXOMSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
12b-acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-26-oic acid
Chemical structure download



12b-Acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-26-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 572.7
Log P RDKit 3.59
Topological polar surface area (Å2) RDKit 155.27
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 41
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 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.72
Shape complexity RDKit 0.72
Number of rotatable bonds SwissADME 8
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



12b-Acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-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
Egan filter RDKit Bad
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 0.39



12b-Acetoxy-3b,7b-dihydroxy-11,15,23-trioxo-lanost-8,16-dien-26-oic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -8.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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