Secondary metabolite: 3α-Oxepanoquercinic acid C



3α-Oxepanoquercinic acid C
Summary
Molecular formula: C31H50O5
SMILES: OC(=O)C([C@H](C1(O)C[C@@H](C)[C@@H]2[C@]3([C@H](O1)CC1=C([C@@]3(CC2)C)CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C)C
InChI: InChI=1S/C31H50O5/c1-17-16-31(35,19(3)18(2)26(33)34)36-25-15-22-21(29(7)14-11-20(17)30(25,29)8)9-10-23-27(4,5)24(32)12-13-28(22,23)6/h17-20,23-25,32,35H,9-16H2,1-8H3,(H,33,34)/t17-,18?,19-,20-,23+,24-,25-,28-,29+,30+,31?/m1/s1
InChIKey: PEJVRURWUPBFOY-KLBYFCBYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
3α-oxepanoquercinic acid c
Chemical structure download



3α-Oxepanoquercinic acid C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 502.74
Log P RDKit 6.18
Topological polar surface area (Å2) RDKit 86.99
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 11
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 28
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.9
Shape complexity RDKit 0.9
Number of rotatable bonds SwissADME 3
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
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 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



3α-Oxepanoquercinic acid C
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 0.4



3α-Oxepanoquercinic acid C
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 High
Log Kp (Skin permeation, cm/s) SwissADME -5.05
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 Yes




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