Secondary metabolite: Antroquinonol B



Antroquinonol B
Summary
Molecular formula: C24H36O6
SMILES: COC1=C(OC)C(=O)[C@@H]([C@H]([C@H]1O)C/C=C(/CC/C=C(/CC1OC(=O)[C@H](C1)C)C)C)C
InChI: InChI=1S/C24H36O6/c1-14(8-7-9-15(2)12-18-13-16(3)24(27)30-18)10-11-19-17(4)20(25)22(28-5)23(29-6)21(19)26/h9-10,16-19,21,26H,7-8,11-13H2,1-6H3/b14-10+,15-9+/t16-,17+,18?,19+,21+/m0/s1
InChIKey: DBMARRQLSJJYJE-JJLRARDYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Terpene lactones
Synonymous chemical names:
antroquinonol b
Chemical structure download



Antroquinonol B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 420.55
Log P RDKit 4.09
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 16
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.67
Shape complexity RDKit 0.67
Number of rotatable bonds SwissADME 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



Antroquinonol B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.45



Antroquinonol B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.72
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




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