Secondary metabolite: Ganofuran B



Ganofuran B
Summary
Molecular formula: C21H26O4
SMILES: C/C(=CCCC(c1cc2c(o1)ccc(c2)O)C(=O)O)/CCC=C(C)C
InChI: InChI=1S/C21H26O4/c1-14(2)6-4-7-15(3)8-5-9-18(21(23)24)20-13-16-12-17(22)10-11-19(16)25-20/h6,8,10-13,18,22H,4-5,7,9H2,1-3H3,(H,23,24)/b15-8+
InChIKey: XZFXVBWSDABZIS-OVCLIPMQSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Sesquiterpenoids
Synonymous chemical names:
ganofuran b
Chemical structure download



Ganofuran B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 342.44
Log P RDKit 5.78
Topological polar surface area (Å2) RDKit 70.67
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.38
Shape complexity RDKit 0.38
Number of rotatable bonds SwissADME 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2



Ganofuran 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 1
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 0.6



Ganofuran B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately 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 -4.36
Number of PAINS structural alerts SwissADME 0
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