IMPPAT Phytochemical information: 
(2R)-2-[(1S)-1-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
(2R)-2-[(1S)-1-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Summary

SMILES: OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@H](O)C=C2[C@]1(C)C(=O)C=CC2)C
InChI: InChI=1S/C28H38O5/c1-15-12-23(33-26(32)18(15)14-29)16(2)19-8-9-20-25-21(10-11-27(19,20)3)28(4)17(13-22(25)30)6-5-7-24(28)31/h5,7,13,16,19-23,25,29-30H,6,8-12,14H2,1-4H3/t16-,19+,20-,21-,22+,23+,25-,27+,28-/m0/s1
InChIKey: UKCDPEQADUKCDH-NQNHUYFBSA-N
DeepSMILES: OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6[C@H]O)C=C[C@]6C)C=O)C=CC6)))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC2C4C(=O)C=CCC4=CCC23)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C3CCC3CCCC(O)C32)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C3CCC3CCCC(C)C32)C1
Functional groups: CC(C)=CC; CC1=C(C)C(=O)OCC1; CC=CC(C)=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
daturataturin
External chemical identifiers:
CID:91885231; ZINC:ZINC000096023898; MolPort-035-706-503
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2R)-2-[(1S)-1-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
(2R)-2-[(1S)-1-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49
(2R)-2-[(1S)-1-[(7S,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.88
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes