Secondary metabolite: 16α,25-Dihydroxyeburiconic acid



16α,25-Dihydroxyeburiconic acid
Summary
Molecular formula: C31H48O5
SMILES: OC(=O)[C@@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CCC(=C)C(O)(C)C
InChI: InChI=1S/C31H48O5/c1-18(28(4,5)36)9-10-19(26(34)35)25-22(32)17-31(8)21-11-12-23-27(2,3)24(33)14-15-29(23,6)20(21)13-16-30(25,31)7/h19,22-23,25,32,36H,1,9-17H2,2-8H3,(H,34,35)/t19-,22-,23+,25+,29-,30-,31+/m1/s1
InChIKey: YEXYFLGTSGQWMI-IMOFTLGFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
16α,25-dihydroxyeburiconic acid
Chemical structure download



16α,25-Dihydroxyeburiconic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 500.72
Log P RDKit 6.08
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 25
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.81
Shape complexity RDKit 0.81
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



16α,25-Dihydroxyeburiconic 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 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.38



16α,25-Dihydroxyeburiconic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately 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 -5.87
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