Secondary metabolite: 5α,6α-Epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol



5α,6α-Epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol
Summary
Molecular formula: C28H44O3
SMILES: O[C@H]1CC[C@]2([C@@]3(C1)O[C@H]3[C@H](C1=C3[C@@](CC[C@H]21)(C)[C@H](CC3)[C@@H](/C=C/[C@@H](C(C)C)C)C)O)C
InChI: InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-23-22(12-13-26(20,21)5)27(6)14-11-19(29)15-28(27)25(31-28)24(23)30/h7-8,16-20,22,24-25,29-30H,9-15H2,1-6H3/b8-7+/t17-,18+,19-,20+,22-,24-,25-,26+,27+,28-/m0/s1
InChIKey: MEIJIKXWOMTKCH-SDNRFBISSA-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:
5α,6α-epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol
Chemical structure download



5α,6α-Epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 428.66
Log P RDKit 5.66
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 10
Stereochemical complexity RDKit 0.36
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



5α,6α-Epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol
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
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 0.45



5α,6α-Epoxy-(22e,24r)-ergosta-8(14),22-diene-3β,7α-diol
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.27
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