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Record Information
Version4.0
Creation Date2014-10-08 15:55:35 UTC
Update Date2017-09-27 08:44:15 UTC
HMDB IDHMDB0061837
Secondary Accession Numbers
  • HMDB61837
Metabolite Identification
Common NameCalamenene
DescriptionCalamenene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H22
Average Molecular Weight202.3352
Monoisotopic Molecular Weight202.172150704
IUPAC Name(1R,4R)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene
Traditional Name(1R,4R)-4-isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene
CAS Registry NumberNot Available
SMILES
[H][C@@]1(C)CC[C@]([H])(C(C)C)C2=C1C=CC(C)=C2
InChI Identifier
InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3/t12-,13-/m1/s1
InChI KeyPGTJIOWQJWHTJJ-CHWSQXEVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Tetralin
  • Benzenoid
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP5.6ALOGPS
logP5.24ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.83 m³·mol⁻¹ChemAxon
Polarizability25.69 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-50eb27f5affc2227db9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pba-6920000000-8e2388350eb54cd43459View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9600000000-01b8646e70d9f4f36275View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-3c8f8628087632213a56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-5c05a8c35f57a6319a4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-0910000000-72bf210a7cc602013a4aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11298625
PDB IDNot Available
ChEBI ID88614
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melcher E, Jungel P, Mollendorf B, Schmitt U: Identification of a hydroxy substituted calamenene--a sesquiterpene associated with wound reactions in non-infected xylem of Tilia spp. Phytochemistry. 2003 Mar;62(5):707-13. [PubMed:12620322 ]
  2. Takei M, Umeyama A, Arihara S: T-cadinol and calamenene induce dendritic cells from human monocytes and drive Th1 polarization. Eur J Pharmacol. 2006 May 10;537(1-3):190-9. Epub 2006 Mar 3. [PubMed:16631732 ]
  3. Salmoun M, Braekman JC, Ranarivelo Y, Rasamoelisendra R, Ralambomanana D, Dewelle J, Darro F, Kiss R: New calamenene sesquiterpenes from Tarenna madagascariensis. Nat Prod Res. 2007 Feb;21(2):111-20. [PubMed:17365697 ]
  4. Morimoto M, Cantrell CL, Libous-Bailey L, Duke SO: Phytotoxicity of constituents of glandular trichomes and the leaf surface of camphorweed, Heterotheca subaxillaris. Phytochemistry. 2009 Jan;70(1):69-74. doi: 10.1016/j.phytochem.2008.09.026. Epub 2008 Dec 4. [PubMed:19054533 ]
  5. Schrems MG, Pfaltz A: NeoPHOX--an easily accessible P,N-ligand for iridium-catalyzed asymmetric hydrogenation: preparation, scope and application in the synthesis of demethyl methoxycalamenene. Chem Commun (Camb). 2009 Nov 7;(41):6210-2. doi: 10.1039/b912680e. Epub 2009 Aug 27. [PubMed:19826671 ]
  6. Limna Mol VP, Raveendran TV, Naik BG, Kunnath RJ, Parameswaran PS: Calamenenes--aromatic bicyclic sesquiterpenes--from the Indian gorgonian Subergorgia reticulata (Ellis and Solander, 1786). Nat Prod Res. 2011 Jan;25(2):169-74. doi: 10.1080/14786419.2010.495069. [PubMed:21246444 ]
  7. Murugan R, Mallavarapu GR: Composition of the essential oil of Pogostemon travancoricus var. travancoricus. Nat Prod Commun. 2012 Jan;7(1):87-8. [PubMed:22428255 ]
  8. Dai Y, Harinantenaina L, Brodie PJ, Callmander MW, Randrianasolo S, Rakotobe E, Rasamison VE, Kingston DG: Isolation and synthesis of two antiproliferative calamenene-type sesquiterpenoids from Sterculia tavia from the Madagascar rain forest. Bioorg Med Chem. 2012 Dec 15;20(24):6940-4. doi: 10.1016/j.bmc.2012.10.012. Epub 2012 Oct 23. [PubMed:23149304 ]
  9. Azevedo MM, Chaves FC, Almeida CA, Bizzo HR, Duarte RS, Campos-Takaki GM, Alviano CS, Alviano DS: Antioxidant and antimicrobial activities of 7-hydroxy-calamenene-rich essential oils from Croton cajucara Benth. Molecules. 2013 Jan 16;18(1):1128-37. doi: 10.3390/molecules18011128. [PubMed:23325101 ]
  10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. MetaCyc: cis-calamenene related sesquiterpenoids biosynthesis [Link]