IMPPAT Phytochemical information: 
Dihydroferuperine

Dihydroferuperine
Summary

SMILES: COC1=CC(=CCC1O)/C=C\C=C\C(=O)N1CCCCC1
InChI: InChI=1S/C17H23NO3/c1-21-16-13-14(9-10-15(16)19)7-3-4-8-17(20)18-11-5-2-6-12-18/h3-4,7-9,13,15,19H,2,5-6,10-12H2,1H3/b7-3-,8-4+
InChIKey: PUYWOMGLUNDEFM-KYPMKJFLSA-N
DeepSMILES: COC=CC=CCC6O))))/C=C\C=C\C=O)NCCCCC6
Scaffold Graph/Node/Bond level: O=C(C=CC=CC1=CCCC=C1)N1CCCCC1
Scaffold Graph/Node level: OC(CCCCC1CCCCC1)N1CCCCC1
Scaffold Graph level: CC(CCCCC1CCCCC1)C1CCCCC1
Functional groups: COC1=CC(/C=C\C=C\C(=O)N(C)C)=CCC1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Piperidines
ClassyFire Subclass: N-acylpiperidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
dihydroferuperine
External chemical identifiers:
CID:CID_131752910; ChEBI:CHEBI:174060
Chemical structure download


Dihydroferuperine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 289.38
Log P RDKit 2.33
Topological polar surface area (Å2) RDKit 49.77
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Dihydroferuperine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.64


Dihydroferuperine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.67
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No