Secondary metabolite: 3,4-Seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone



3,4-Seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone
Summary
Molecular formula: C30H48O5
SMILES: CC(CCC[C@H](C1CC[C@@]2([C@]1(C)CC[C@]13[C@@]2(CCC2[C@]3(C)CCC(=O)OC2(C)C)O1)C)C(=O)O)C
InChI: InChI=1S/C30H48O5/c1-19(2)9-8-10-20(24(32)33)21-11-15-28(7)26(21,5)17-18-29-27(6)14-13-23(31)34-25(3,4)22(27)12-16-30(28,29)35-29/h19-22H,8-18H2,1-7H3,(H,32,33)/t20-,21?,22?,26-,27+,28-,29+,30+/m1/s1
InChIKey: NFGIXKPDIYJFHW-PENNDKJGSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3,4-seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone
Chemical structure download



3,4-Seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 488.71
Log P RDKit 6.77
Topological polar surface area (Å2) RDKit 76.13
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 28
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.93
Shape complexity RDKit 0.93
Number of rotatable bonds SwissADME 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



3,4-Seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone
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 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 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.33



3,4-Seco-8α,9α-epoxy-5α-lanosta-21-oic acid 3,4 lactone
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -4.58
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