Secondary metabolite: Gargalol A



Gargalol A
Summary
Molecular formula: C28H44O3
SMILES: CC([C@H](/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=C[C@@H]([C@]23[C@]1(C)CC[C@@H]([C@@H]3O2)O)O)C)C)C
InChI: InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-19-15-24(30)28-25(31-28)23(29)12-14-27(28,6)22(19)11-13-26(20,21)5/h7-8,15-18,20-25,29-30H,9-14H2,1-6H3/b8-7+/t17-,18+,20+,21-,22-,23-,24-,25-,26+,27+,28-/m0/s1
InChIKey: VSKOELNSOFBWQU-VNQQHNGCSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Ergostane steroids
Synonymous chemical names:
gargalol a
Chemical structure download



Gargalol A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 428.66
Log P RDKit 5.51
Topological polar surface area (Å2) RDKit 52.99
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 24
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.86
Shape complexity RDKit 0.86
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 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Gargalol A
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
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 0.46



Gargalol A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.93
Number of PAINS structural alerts SwissADME 0
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 No




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