Secondary metabolite: 3,14,25-Trihydroxy-24-hydroxymethylergosta-7,22-dien-6-one



3,14,25-Trihydroxy-24-hydroxymethylergosta-7,22-dien-6-one
Summary
Molecular formula: C28H44O5
SMILES: OC[C@H](C(O)(C)C)/C=C/[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@@H]2[C@]1(C)CC[C@@H](C2)O)O)C
InChI: InChI=1S/C28H44O5/c1-17(6-7-18(16-29)25(2,3)32)20-10-13-28(33)22-15-24(31)23-14-19(30)8-11-26(23,4)21(22)9-12-27(20,28)5/h6-7,15,17-21,23,29-30,32-33H,8-14,16H2,1-5H3/b7-6+/t17-,18-,19+,20-,21+,23-,26-,27-,28-/m1/s1
InChIKey: KZXSEYDTLJXXRM-DQXYIBCXSA-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:
3,14,25-trihydroxy-24-hydroxymethylergosta-7,22-dien-6-one
Chemical structure download



3,14,25-Trihydroxy-24-hydroxymethylergosta-7,22-dien-6-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 460.65
Log P RDKit 3.79
Topological polar surface area (Å2) RDKit 97.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
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 9
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.82
Shape complexity RDKit 0.82
Number of rotatable bonds SwissADME 5
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



3,14,25-Trihydroxy-24-hydroxymethylergosta-7,22-dien-6-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 0.47



3,14,25-Trihydroxy-24-hydroxymethylergosta-7,22-dien-6-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 -7.38
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 Yes




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