IMPPAT Phytochemical information: 
Nepetalic acid

Nepetalic acid
Summary

SMILES: O=C[C@@H]([C@H]1CC[C@@H]([C@H]1C(=O)O)C)C
InChI: InChI=1S/C10H16O3/c1-6-3-4-8(7(2)5-11)9(6)10(12)13/h5-9H,3-4H2,1-2H3,(H,12,13)/t6-,7-,8+,9+/m0/s1
InChIKey: RGTMAXSVLBZNEL-RBXMUDONSA-N
DeepSMILES: O=C[C@@H][C@H]CC[C@@H][C@H]5C=O)O)))C)))))C
Scaffold Graph/Node/Bond level: C1CCCC1
Scaffold Graph/Node level: C1CCCC1
Scaffold Graph level: C1CCCC1
Functional groups: CC=O; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Monoterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
nepetolactone [3], Nepetalic acid, nepetalic acid, nepetolactone [2], nepetalic acid [l]
External chemical identifiers:
CID:CID_5486616
Chemical structure download


Nepetalic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 184.24
Log P RDKit 1.57
Topological polar surface area (Å2) RDKit 54.37
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 3
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


Nepetalic acid
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 0.677171


Nepetalic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -6.24
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