Secondary metabolite: 5α,8α-Epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside



5α,8α-Epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside
Summary
Molecular formula: C34H54O8
SMILES: OCC1OC(O[C@H]2CC[C@]3([C@]4(C2)OO[C@]2(C3CC[C@]3(C2CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C=C4)C)C(C(C1O)O)O
InChI: InChI=1S/C34H54O8/c1-19(2)20(3)7-8-21(4)23-9-10-25-31(23,5)13-12-26-32(6)14-11-22(17-33(32)15-16-34(25,26)42-41-33)39-30-29(38)28(37)27(36)24(18-35)40-30/h7-8,15-16,19-30,35-38H,9-14,17-18H2,1-6H3/b8-7+/t20-,21+,22-,23+,24?,25?,26?,27?,28?,29?,30?,31+,32+,33-,34+/m0/s1
InChIKey: CKJZKFPVVUQBMB-AOHVSNAWSA-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:
5α,8α-epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside
Chemical structure download



5α,8α-Epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 590.8
Log P RDKit 4.3
Topological polar surface area (Å2) RDKit 117.84
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 34
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 30
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.88
Shape complexity RDKit 0.88
Number of rotatable bonds SwissADME 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7



5α,8α-Epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside
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 3
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 0.26



5α,8α-Epidioxy-24(r)-methylcholesta-6,22-dien-3β-d-glucopyranoside
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.27
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 Yes




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