Secondary metabolite: 3a,15a -Diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-oic acid



3a,15a -Diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-oic acid
Summary
Molecular formula: C34H50O7
SMILES: CC(=O)O[C@H]1C[C@@H]([C@@]2([C@]1(C)C1=CCC3[C@](C1=CC2)(C)CC[C@H](C3(C)C)OC(=O)C)C)C([C@@H](C/C=C(/C(=O)O)C)O)C
InChI: InChI=1S/C34H50O7/c1-19(30(38)39)10-12-26(37)20(2)25-18-29(41-22(4)36)34(9)24-11-13-27-31(5,6)28(40-21(3)35)15-16-32(27,7)23(24)14-17-33(25,34)8/h10-11,14,20,25-29,37H,12-13,15-18H2,1-9H3,(H,38,39)/b19-10+/t20?,25-,26-,27?,28-,29+,32-,33-,34-/m1/s1
InChIKey: XITBGHDSLKRVMR-GJGAYOQOSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3a,15a -diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-oic acid, 3a,15a-diacetoxy-22a-hydroxylanosta-7,9(11),24- trien-26-oic acid
Chemical structure download



3a,15a -Diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-oic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 570.77
Log P RDKit 6.4
Topological polar surface area (Å2) RDKit 110.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 25
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.74
Shape complexity RDKit 0.74
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



3a,15a -Diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-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,15a -Diacetoxy-22a -hydroxylanosta-7,9(11),24-trien-26-oic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -5.55
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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