IMPPAT Phytochemical information: 
(1S,3R,8S,11S,12S,15R,16R)-15-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-12,16-dimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
(1S,3R,8S,11S,12S,15R,16R)-15-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-12,16-dimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Summary

SMILES: O=C1CC[C@]23[C@H](C1)CC[C@@H]1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2[C@@H](CC[C@@H](C(=C)C)C)C)C
InChI: InChI=1S/C29H46O/c1-19(2)20(3)7-8-21(4)24-12-13-27(6)25-10-9-22-17-23(30)11-14-28(22)18-29(25,28)16-15-26(24,27)5/h20-22,24-25H,1,7-18H2,2-6H3/t20-,21+,22-,24+,25-,26+,27-,28+,29-/m0/s1
InChIKey: UWHKELQKZGZXIE-MHERODDWSA-N
DeepSMILES: O=CCC[C@@][C@H]C6)CC[C@@H][C@@]6C7)CC[C@][C@@]6C)CC[C@@H]5[C@@H]CC[C@@H]C=C)C))C))))C))))))C
Scaffold Graph/Node/Bond level: O=C1CCC23CC24CCC2CCCC2C4CCC3C1
Scaffold Graph/Node level: OC1CCC23CC24CCC2CCCC2C4CCC3C1
Scaffold Graph level: CC1CCC23CC24CCC2CCCC2C4CCC3C1
Functional groups: CC(=O)C; 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: Ergostane steroids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids|Triterpenoids
NP Classifier Class: Cholestane steroids|Cycloartane triterpenoids
Synonymous chemical names:
28-norcyclomusalenone
External chemical identifiers:
CID:CID_102121397; ZINC:ZINC000255272306
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,3R,8S,11S,12S,15R,16R)-15-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-12,16-dimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.69
Log P RDKit 7.99
Topological polar surface area (Å2) RDKit 17.07
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1S,3R,8S,11S,12S,15R,16R)-15-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-12,16-dimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42
(1S,3R,8S,11S,12S,15R,16R)-15-[(2R,5S)-5,6-dimethylhept-6-en-2-yl]-12,16-dimethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -2.29
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 No