IMPPAT Phytochemical information: 
Nepetaefolinol

Nepetaefolinol
Summary

SMILES: OC1C[C@@H](C)[C@@]2([C@]34C1[C@](C)(CCC3)C(=O)OC4)CCC1(O2)CCOC1=O
InChI: InChI=1S/C20H28O6/c1-12-10-13(21)14-17(2)4-3-5-18(14,11-25-15(17)22)20(12)7-6-19(26-20)8-9-24-16(19)23/h12-14,21H,3-11H2,1-2H3/t12-,13?,14?,17+,18-,19?,20-/m1/s1
InChIKey: BTDGKVYVOVKLMN-JDQJVEPXSA-N
DeepSMILES: OCC[C@@H]C)[C@@][C@]C6[C@]C)CCC6)))C=O)OC6))))))CCCO5)CCOC5=O
Scaffold Graph/Node/Bond level: O=C1OCC23CCCC1C2CCCC31CCC2(CCOC2=O)O1
Scaffold Graph/Node level: OC1OCC23CCCC1C2CCCC31CCC2(CCOC2O)O1
Scaffold Graph level: CC1CCC23CCCC1C2CCCC31CCC2(CCCC2C)C1
Functional groups: CO; COC(=O)C; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Lactones
ClassyFire Subclass: Delta valerolactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids
Synonymous chemical names:
nepetaefolinol, Nepetaefolinol
External chemical identifiers:
CID:CID_5458433
Chemical structure download


Nepetaefolinol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 364.44
Log P RDKit 1.97
Topological polar surface area (Å2) RDKit 82.06
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
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 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Nepetaefolinol
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.662008


Nepetaefolinol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.06
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 Yes