Secondary metabolite: Bovistol A



Bovistol A
Summary
Molecular formula: C30H40O6
SMILES: OCCc1c2CC[C@]3(Oc2c2c(c1C)C[C@@](C2)(C)CO)C(=O)[C@@]1(O)C[C@](CC1=C(C13CC1)C)(C)CO
InChI: InChI=1S/C30H40O6/c1-17-19(6-10-31)20-5-7-30(36-24(20)22-12-26(3,15-32)11-21(17)22)25(34)29(35)14-27(4,16-33)13-23(29)18(2)28(30)8-9-28/h31-33,35H,5-16H2,1-4H3/t26-,27-,29-,30+/m1/s1
InChIKey: NMEHSFIENJDJIR-OQGMSKNBSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Sesquiterpenoids
Synonymous chemical names:
bovistol a
Chemical structure download



Bovistol A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 496.64
Log P RDKit 2.89
Topological polar surface area (Å2) RDKit 107.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 21
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.7
Shape complexity RDKit 0.7
Number of rotatable bonds SwissADME 4
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
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 6



Bovistol 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 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48



Bovistol A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.65
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