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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-12-06 16:20:48 UTC
Update Date2017-12-07 15:46:13 UTC
HMDB IDHMDB0059698
Secondary Accession Numbers
  • HMDB59698
Metabolite Identification
Common NameCadalene
DescriptionCadalene (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants. Cadalene, together with retene, simonellite and ip-iHMN, is a biomarker of higher plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene to cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H18
Average Molecular Weight198.3034
Monoisotopic Molecular Weight198.140850576
IUPAC Name1,6-dimethyl-4-(propan-2-yl)naphthalene
Traditional Namecadalene
CAS Registry NumberNot Available
SMILES
CC(C)C1=C2C=C(C)C=CC2=C(C)C=C1
InChI Identifier
InChI=1S/C15H18/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-10H,1-4H3
InChI KeyVMOJIHDTVZTGDO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Naphthalene
  • Cumene
  • Benzenoid
  • Polycyclic hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

  Subcellular:

  Biofluid and excreta:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00017 g/LALOGPS
logP5.7ALOGPS
logP5.23ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability24.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-e03a05ac04da9143239aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-f2bd9379af6776ffe038View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-73c91ba9d394b3ebe92bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ai-2900000000-96f07179112485b07595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-6d71e27487a53d2cadb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-06a8768f6d6deeea25b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053s-0900000000-a50f7e0957ce60590146View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005459
KNApSAcK IDNot Available
Chemspider ID9808
KEGG Compound IDNot Available
BioCyc IDCPD-8806
BiGG IDNot Available
Wikipedia LinkCadalene
METLIN IDNot Available
PubChem Compound10225
PDB IDNot Available
ChEBI IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.