Secondary metabolite: (3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one

(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one
Summary
Molecular formula: C22H34O4
SMILES: O[C@@H]1CC[C@]2([C@H]([C@@H]1C)CC(=O)C1=C2CC[C@]2([C@H]1CC[C@]2(O)[C@H](O)C)C)C
InChI: InChI=1S/C22H34O4/c1-12-16-11-18(25)19-14(20(16,3)8-7-17(12)24)5-9-21(4)15(19)6-10-22(21,26)13(2)23/h12-13,15-17,23-24,26H,5-11H2,1-4H3/t12-,13+,15-,16-,17+,20+,21-,22-/m0/s1
InChIKey: MHAYDOHKEQXCEG-GLVQIBCTSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Androstane steroids
Synonymous chemical names:
(3r,4s,5s,17r,20r)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.51
Log P RDKit 2.99
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 19
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.86
Shape complexity RDKit 0.86
Number of rotatable bonds SwissADME 1
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.67
(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.17
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