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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 02:43:45 UTC
Update Date2021-09-23 02:43:46 UTC
HMDB IDHMDB0301815
Secondary Accession NumbersNone
Metabolite Identification
Common Name(+)-Camphene
DescriptionCamphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian.
Structure
Thumb
Synonyms
ValueSource
(+)-CompheneChEBI
(1R)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
(1R,4S)-(+)-CampheneChEBI
(1R,4S)-2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
(1R,4S)-CampheneChEBI
D-CampheneChEBI
(+)-CamphenePhytoBank
(1R)-CamphenePhytoBank
(±)-CamphenePhytoBank
2,2-Dimethyl-3-methylenenorbornanePhytoBank
2-Methylene-3,3-dimethylbicyclo[2.2.1]heptanePhytoBank
3,3-Dimethyl-2-methylenenorbornanePhytoBank
3,3-Dimethyl-2-methylenenorcamphanePhytoBank
dl-CamphenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1R,4S)-2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
Traditional Name(+)-camphene
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H]2CC[C@@H](C2)C1=C
InChI Identifier
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9+/m0/s1
InChI KeyCRPUJAZIXJMDBK-DTWKUNHWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot 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
logP4.56ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+127.96932859911
AllCCS[M+H-H2O]+123.43732859911
AllCCS[M+Na]+133.41732859911
AllCCS[M+NH4]+132.19732859911
AllCCS[M-H]-132.40932859911
AllCCS[M+Na-2H]-133.88832859911
AllCCS[M+HCOO]-135.57532859911
DeepCCS[M+H]+135.6230932474
DeepCCS[M-H]-133.22530932474
DeepCCS[M-2H]-167.78730932474
DeepCCS[M+Na]+142.44830932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 10V, Positive-QTOFsplash10-000i-0900000000-196b02102f0ebf09b5342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 20V, Positive-QTOFsplash10-000i-2900000000-c52b7cd8940e2fb05c542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 40V, Positive-QTOFsplash10-014i-9000000000-6f9543516068b727c1562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 10V, Negative-QTOFsplash10-000i-0900000000-cce5a3a8054b82bf623f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 20V, Negative-QTOFsplash10-000i-0900000000-cce5a3a8054b82bf623f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 40V, Negative-QTOFsplash10-014i-2900000000-3b379a5acd27d5e4086c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 10V, Positive-QTOFsplash10-014s-9300000000-10513da20f6a7537fd9b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 20V, Positive-QTOFsplash10-06fu-9500000000-5bf329b2ba88ea32211b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 40V, Positive-QTOFsplash10-0693-9300000000-cc0f0b0ffa4549f4dcfc2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Camphene 40V, Negative-QTOFsplash10-001r-0900000000-5f08b0d51d8859e573d82021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001453
KNApSAcK IDC00000818
Chemspider ID83259
KEGG Compound IDC06304
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92221
PDB IDNot Available
ChEBI ID20
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1106261
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]