IMPPAT Phytochemical information: 
Azulene

Azulene
Summary

SMILES: c1ccc2-c(cc1)ccc2
InChI: InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
InChIKey: CUFNKYGDVFVPHO-UHFFFAOYSA-N
DeepSMILES: cccc-ccc7))ccc5
Scaffold Graph/Node/Bond level: c1ccc2cccc-2cc1
Scaffold Graph/Node level: C1CCC2CCCC2CC1
Scaffold Graph level: C1CCC2CCCC2CC1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Hydrocarbons
ClassyFire Class: Unsaturated hydrocarbons
ClassyFire Subclass: Olefins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
Azulene, azulene, azulen
External chemical identifiers:
CID:CID_9231; ChEMBL:CHEMBL3272628; ChEBI:CHEBI:31249; ZINC:ZINC000001570209; FDASRS:82R6M9MGLP; SureChEMBL:SCHEMBL8463; MolPort-001-787-037
Chemical structure download


Azulene
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 128.17
Log P RDKit 2.79
Topological polar surface area (Å2) RDKit 0
Number of hydrogen bond acceptors RDKit 0
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 10
Number of heteroatoms RDKit 0
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Azulene
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 2
Ghose rule RDKit Failed
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 0.51


Azulene
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No