IMPPAT Phytochemical information: 
Lupanone

Lupanone
Summary

SMILES: CC(C1CC[C@]2(C1C1CCC3[C@@]([C@]1(C)CC2)(C)CCC1[C@]3(C)C(=O)CCC1(C)C)C)C
InChI: InChI=1S/C30H50O/c1-19(2)20-11-15-27(5)17-18-28(6)21(25(20)27)9-10-23-29(28,7)16-12-22-26(3,4)14-13-24(31)30(22,23)8/h19-23,25H,9-18H2,1-8H3/t20?,21?,22?,23?,25?,27-,28-,29-,30+/m1/s1
InChIKey: NLTVGCSJCAMTNB-HPEVILAGSA-N
DeepSMILES: CCCCC[C@]C5CCCC[C@@][C@]6C)CC%10)))C)CCC[C@]6C)C=O)CCC6C)C)))))))))))))))C)))))C
Scaffold Graph/Node/Bond level: O=C1CCCC2CCC3C4CCC5CCCC5C4CCC3C12
Scaffold Graph/Node level: OC1CCCC2CCC3C4CCC5CCCC5C4CCC3C12
Scaffold Graph level: CC1CCCC2CCC3C4CCC5CCCC5C4CCC3C12
Functional groups: CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Lupane triterpenoids
Synonymous chemical names:
lupanone, Lupanone
External chemical identifiers:
CID:CID_129730785
Chemical structure download


Lupanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 426.73
Log P RDKit 8.31
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 30
Number of heavy atoms RDKit 31
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 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 29
Shape complexity RDKit 0.97
Number of rotatable bonds RDKit 1
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


Lupanone
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.411754


Lupanone
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 -2.07
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 No