Secondary metabolite: Ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)



Ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)
Summary
Molecular formula: C27H42O2
SMILES: CCC(/C=C/C(C1CCC2C1(C)CCC1[C@@]32C=C[C@]2(O3)C1(C)CCC(C2)O)C)C
InChI: InChI=1S/C27H42O2/c1-6-18(2)7-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)29-26/h7-8,15-16,18-23,28H,6,9-14,17H2,1-5H3/b8-7+/t18?,19?,20?,21?,22?,23?,24?,25?,26-,27+/m1/s1
InChIKey: PVINRKSCUKBIOV-OKYFRUPUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Synonymous chemical names:
ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)
Chemical structure download



Ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 398.63
Log P RDKit 6.3
Topological polar surface area (Å2) RDKit 29.46
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.37
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.85
Shape complexity RDKit 0.85
Number of rotatable bonds SwissADME 4
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)
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 2
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 0.56



Ergosta-5α,8α-epidioxy-6,22-dien-3β-ol(ergosteryl peroxide)
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -4.18
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 No
P-glycoprotein substrate SwissADME No




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