Secondary metabolite: 3a-Acetoxy-5a-lanosta-8,24(240)-dien-21-oic acid



3a-Acetoxy-5a-lanosta-8,24(240)-dien-21-oic acid
Summary
Molecular formula: C33H52O4
SMILES: CC(=O)O[C@@H]1CC[C@]2([C@@](C1(C)C)(C)CCC1=C2CC[C@]2(C1CC[C@@H]2[C@H](C(=O)O)CCC(=C)C(C)C)C)C
InChI: InChI=1S/C33H52O4/c1-20(2)21(3)10-11-24(29(35)36)26-13-12-25-23-14-19-33(9)30(5,6)28(37-22(4)34)16-18-32(33,8)27(23)15-17-31(25,26)7/h20,24-26,28H,3,10-19H2,1-2,4-9H3,(H,35,36)/t24-,25?,26-,28-,31+,32-,33+/m1/s1
InChIKey: PNIGSCJUSUPUOR-VWTZMXRKSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3a-acetoxy-5a-lanosta-8,24(240)-dien-21-oic acid
Chemical structure download



3a-Acetoxy-5a-lanosta-8,24(240)-dien-21-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 512.77
Log P RDKit 8.36
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 37
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 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 27
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.82
Shape complexity RDKit 0.82
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



3a-Acetoxy-5a-lanosta-8,24(240)-dien-21-oic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
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 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.27



3a-Acetoxy-5a-lanosta-8,24(240)-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 Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.45
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 Yes




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