Secondary metabolite: 3-Epidehydropachymic acid



3-Epidehydropachymic acid
Summary
Molecular formula: C33H50O5
SMILES: CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)CC=C1C2=CC[C@]2([C@@]1(C)C[C@H]([C@@H]2[C@H](C(=O)O)CCC(=C)C(C)C)O)C)C
InChI: InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27-,28+,31-,32-,33+/m1/s1
InChIKey: RWIALJIVPUCERT-ROLXBSRMSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3-epidehydropachymic acid
Chemical structure download



3-Epidehydropachymic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 526.76
Log P RDKit 7.11
Topological polar surface area (Å2) RDKit 83.83
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 38
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 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 25
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.76
Shape complexity RDKit 0.76
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



3-Epidehydropachymic 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



3-Epidehydropachymic 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 -4.59
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 Yes
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