Secondary metabolite: Ganoboninone B



Ganoboninone B
Summary
Molecular formula: C30H40O8
SMILES: CCC(=O)CC[C@]1(C)OC[C@]23[C@@H]1CC[C@@]3(C)C1=C(C(=O)C2=O)[C@@](C)(CCC(=O)OC)[C@@H](CC1=O)[C@]1(C)OC1
InChI: InChI=1S/C30H40O8/c1-7-17(31)8-13-28(4)19-9-12-27(3)22-18(32)14-20(29(5)15-37-29)26(2,11-10-21(33)36-6)23(22)24(34)25(35)30(19,27)16-38-28/h19-20H,7-16H2,1-6H3/t19-,20-,26+,27+,28+,29-,30+/m1/s1
InChIKey: RHYMEQIZAITVCZ-JTJVRMFXSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Fatty Acyls
Sub class: Fatty acid esters
Synonymous chemical names:
ganoboninone b
Chemical structure download



Ganoboninone B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 528.64
Log P RDKit 3.72
Topological polar surface area (Å2) RDKit 116.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
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 7
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.77
Shape complexity RDKit 0.77
Number of rotatable bonds SwissADME 9
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 2
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 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Ganoboninone B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan 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 0.27



Ganoboninone B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -8.32
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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