IMPPAT Phytochemical information: 
Grasshopper ketone

Grasshopper ketone
Summary

SMILES: CC(=O)C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)O
InChI: InChI=1S/C13H20O3/c1-9(14)5-6-11-12(2,3)7-10(15)8-13(11,4)16/h5,10,15-16H,7-8H2,1-4H3/t6?,10-,13+/m0/s1
InChIKey: QMXLZUOHZGYGDY-JBGXHEPSSA-N
DeepSMILES: CC=O)C=C=CCC)C)C[C@@H]C[C@@]6C)O)))O
Scaffold Graph/Node/Bond level: C=C1CCCCC1
Scaffold Graph/Node level: CC1CCCCC1
Scaffold Graph level: CC1CCCCC1
Functional groups: CC(=O)C=C=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Apocarotenoids
NP Classifier Class: Apocarotenoids (β-)|Megastigmanes
Synonymous chemical names:
grasshopper ketone, Grasshopperketone, grasshopper ketone
External chemical identifiers:
CID:CID_13922639; ChEMBL:CHEMBL4215207; ZINC:ZINC000012153038
Chemical structure download


Grasshopper ketone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 224.3
Log P RDKit 1.59
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 16
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


Grasshopper ketone
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 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.525041


Grasshopper ketone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.69
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