Secondary metabolite: Betulinan A



Betulinan A
Summary
Molecular formula: C20H16O4
SMILES: COC1=C(c2ccccc2)C(=O)C(=C(C1=O)c1ccccc1)OC
InChI: InChI=1S/C20H16O4/c1-23-19-15(13-9-5-3-6-10-13)18(22)20(24-2)16(17(19)21)14-11-7-4-8-12-14/h3-12H,1-2H3
InChIKey: WEOWAYMMZVELOQ-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic oxygen compounds
Class: Organooxygen compounds
Sub class: Carbonyl compounds
Synonymous chemical names:
betulinan a
Chemical structure download



Betulinan A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 320.34
Log P RDKit 3.25
Topological polar surface area (Å2) RDKit 52.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 2
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.1
Shape complexity RDKit 0.1
Number of rotatable bonds SwissADME 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



Betulinan A
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
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.81



Betulinan A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.66
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No




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