Secondary metabolite: (12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one



(12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one
Summary
Molecular formula: C28H40O5
SMILES: O=C1CC[C@]2(C(=C1)C=CC1=C3[C@@]([C@@H](C[C@H]21)O)(C)[C@H](C[C@H]3O)[C@@H]([C@H]1OC([C@H]([C@@H]1O)C)(C)C)C)C
InChI: InChI=1S/C28H40O5/c1-14(25-24(32)15(2)26(3,4)33-25)19-12-21(30)23-18-8-7-16-11-17(29)9-10-27(16,5)20(18)13-22(31)28(19,23)6/h7-8,11,14-15,19-22,24-25,30-32H,9-10,12-13H2,1-6H3/t14-,15-,19+,20-,21+,22+,24-,25+,27-,28-/m0/s1
InChIKey: FRSKOLKLHJBWOV-QCRCLYHDSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Steroidal glycosides
Synonymous chemical names:
(12β,15β,22r,23s,24s)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one
Chemical structure download



(12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.62
Log P RDKit 3.73
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 5
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 7
Number of sp3 hybridized carbon atoms RDKit 21
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.75
Shape complexity RDKit 0.75
Number of rotatable bonds SwissADME 2
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



(12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
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 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.59



(12β,15β,22R,23S,24S)-22,25-epoxy-12,15,23-trihydroxyergost-4,6,8(14)-trien-3-one
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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