Secondary metabolite: 26,27-Dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione



26,27-Dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione
Summary
Molecular formula: C30H44O4
SMILES: OCC(=CCC(=O)[C@H]([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)CO
InChI: InChI=1S/C30H44O4/c1-19(24(33)9-7-20(17-31)18-32)21-11-15-30(6)23-8-10-25-27(2,3)26(34)13-14-28(25,4)22(23)12-16-29(21,30)5/h7-8,12,19,21,25,31-32H,9-11,13-18H2,1-6H3/t19-,21+,25-,28+,29+,30-/m0/s1
InChIKey: RJDPCEHRSNQFNS-ZVUAKGHBSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
26,27-dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione
Chemical structure download



26,27-Dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 468.68
Log P RDKit 5.59
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 22
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.73
Shape complexity RDKit 0.73
Number of rotatable bonds SwissADME 6
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



26,27-Dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione
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 2
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 0.5



26,27-Dihydroxy-5 a -lanosta-7,9(11),24-triene-3,22-dione
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 High
Log Kp (Skin permeation, cm/s) SwissADME -6.08
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 Yes




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