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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:35 UTC
Update Date2022-03-07 03:17:47 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. Calamenene is possibly neutral.
Structure
Data?1563866237
Synonyms
ValueSource
(7R,10R)-CalameneneMeSH
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
Description 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
  • Tetralin
  • Benzenoid
  • Aromatic hydrocarbon
  • Polycyclic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.4231661259
DarkChem[M-H]-150.60831661259
DeepCCS[M+H]+159.71530932474
DeepCCS[M-H]-157.35730932474
DeepCCS[M-2H]-190.75530932474
DeepCCS[M+Na]+165.98130932474
AllCCS[M+H]+144.732859911
AllCCS[M+H-H2O]+140.732859911
AllCCS[M+NH4]+148.532859911
AllCCS[M+Na]+149.632859911
AllCCS[M-H]-154.932859911
AllCCS[M+Na-2H]-155.232859911
AllCCS[M+HCOO]-155.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Calamenene[H][C@@]1(C)CC[C@]([H])(C(C)C)C2=C1C=CC(C)=C21835.4Standard polar33892256
Calamenene[H][C@@]1(C)CC[C@]([H])(C(C)C)C2=C1C=CC(C)=C21511.6Standard non polar33892256
Calamenene[H][C@@]1(C)CC[C@]([H])(C(C)C)C2=C1C=CC(C)=C21526.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calamenene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-1900000000-9f0ccc25841172b472392017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calamenene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 10V, Positive-QTOFsplash10-0udi-0190000000-50eb27f5affc2227db9a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 20V, Positive-QTOFsplash10-0pba-6920000000-8e2388350eb54cd434592017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 40V, Positive-QTOFsplash10-0aor-9600000000-01b8646e70d9f4f362752017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 10V, Negative-QTOFsplash10-0udi-0090000000-3c8f8628087632213a562017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 20V, Negative-QTOFsplash10-0udi-0090000000-5c05a8c35f57a6319a4b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 40V, Negative-QTOFsplash10-0k9i-0910000000-72bf210a7cc602013a4a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 10V, Negative-QTOFsplash10-0udi-0090000000-0b1ac00c3b3c6c0a73b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 20V, Negative-QTOFsplash10-0udi-0090000000-0b1ac00c3b3c6c0a73b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 40V, Negative-QTOFsplash10-0006-2900000000-97f0ac1dc0ccd44df0412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 10V, Positive-QTOFsplash10-0udi-1290000000-7da03440db762e40b1a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 20V, Positive-QTOFsplash10-0006-9620000000-4d8dc0cac0445752868d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calamenene 40V, Positive-QTOFsplash10-0006-9300000000-6fcd0d51379bb93fd0b32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  15. MetaCyc: cis-calamenene related sesquiterpenoids biosynthesis [Link]