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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:48:39 UTC
Update Date2019-07-23 06:21:43 UTC
HMDB IDHMDB0036648
Secondary Accession Numbers
  • HMDB36648
Metabolite Identification
Common Name7-Isopropyl-1,4-dimethylazulene
Description7-Isopropyl-1,4-dimethylazulene, also known as 1,4-dimethyl-7-isopropylazulene or guaiazulene, belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Thus, 7-isopropyl-1,4-dimethylazulene is considered to be an isoprenoid lipid molecule. 7-Isopropyl-1,4-dimethylazulene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862903
Synonyms
ValueSource
1,4-Dimethyl-7-(1-methylethyl)azuleneChEBI
1,4-Dimethyl-7-isopropylazuleneChEBI
3,8-Dimethyl-5-(2-propyl)azuleneChEBI
GuaiazuleneKegg
AzunolKegg
1, 4-Dimethyl-7-isopropylazuleneHMDB
1,3,5,7,9-GuaiapentaeneHMDB
1,4-Dimethyl-7-(1-methyl)-azulene (azulon)HMDB
1,4-Dimethyl-7-(1-methylethyl)-azuleneHMDB
1,4-Dimethyl-7-(1-methylethyl)azulene, 9ciHMDB
1,4-Dimethyl-7-(propan-2-yl)azuleneHMDB
1,4-Dimethyl-7-isopropyl-azuleneHMDB
7-Isopropyl- 1,4-dimethylazuleneHMDB
7-Isopropyl-1,4-dimethyl-azuleneHMDB
AZ-8 berisHMDB
Azulen-berisHMDB
Azulene, 7-isopropyl-1,4-dimethyl- (8ci)HMDB
AzulolHMDB
AzulonHMDB
CuteazulHMDB
EucazulenHMDB
EucazuleneHMDB
GuajazuleneHMDB
GuiazuleneHMDB
GurjunazulenHMDB
HepatoprotectantHMDB
KessazulenHMDB
KessazuleneHMDB
PurazulenHMDB
S-GuaiazuleneHMDB
SilazulonHMDB
UroazulenHMDB
VaumiganHMDB
VetivazulenHMDB
7-Isopropyl-1,4-dimethylazuleneChEBI
Chemical FormulaC15H18
Average Molecular Weight198.3034
Monoisotopic Molecular Weight198.140850576
IUPAC Name1,4-dimethyl-7-(propan-2-yl)azulene
Traditional Nameazulon
CAS Registry Number489-84-9
SMILES
CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1
InChI Identifier
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
InChI KeyFWKQNCXZGNBPFD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGuaianes
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • Azulene
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point31.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00066 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP4.99ALOGPS
logP5.23ChemAxon
logS-3.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability25.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-be4c0960d06735436fe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-3339d5b27a9967e9c5daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-44d06797d9da8aaae9dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-1900000000-6fe86a22e14c459ce6d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-48f7566ceaa93d43c699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-ee4c5f9ee7e99d6db7ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o1-1900000000-e4e77ed98ea343b05eb3Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13329
Phenol Explorer Compound IDNot Available
FooDB IDFDB015573
KNApSAcK IDC00003138
Chemspider ID3395
KEGG Compound IDC09675
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3515
PDB IDNot Available
ChEBI ID5550
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.