IMPPAT Phytochemical information: 
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,6R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,6R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Summary

SMILES: OC[C@@H](CC[C@H]([C@@]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)(O)C)O)C
InChI: InChI=1S/C27H44O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h11,15-16,18,20-23,28,30-34H,5-10,12-14H2,1-4H3/t15-,16+,18+,20-,21+,22+,23-,24-,25-,26-,27-/m1/s1
InChIKey: JQNVCUBPURTQPQ-GYVHUXHASA-N
DeepSMILES: OC[C@@H]CC[C@H][C@@][C@H]CC[C@@][C@]5C)CC[C@H]C6=CC=O)[C@H][C@]6C)C[C@H]O)[C@@H]C6)O)))))))))))))O)))))O)C))O))))C
Scaffold Graph/Node/Bond level: O=C1C=C2C3CCCC3CCC2C2CCCCC12
Scaffold Graph/Node level: OC1CC2C3CCCC3CCC2C2CCCCC12
Scaffold Graph level: CC1CC2C3CCCC3CCC2C2CCCCC12
Functional groups: CO; CC(=O)C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Bile acids, alcohols and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ecdysteroids
Synonymous chemical names:
inokosterone
External chemical identifiers:
CID:CID_441828; ChEBI:CHEBI:27495; ZINC:ZINC000008234185; SureChEMBL:SCHEMBL143421; MolPort-020-005-976
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,6R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 480.64
Log P RDKit 1.71
Topological polar surface area (Å2) RDKit 138.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.89
Number of rotatable bonds RDKit 6
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
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,6R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
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
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.340248
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,6R)-2,3,7-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
ADME 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 -8.78
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