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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 21:43:00 UTC
Update Date2021-09-14 15:45:41 UTC
HMDB IDHMDB0036560
Secondary Accession Numbers
  • HMDB36560
Metabolite Identification
Common Namebeta-Pinene
Description(-)-beta-Pinene, also known as terbenthene or (1S,5S)-b-pinene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (-)-beta-pinene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (-)-beta-Pinene.
Structure
Data?1601236406
Synonyms
ValueSource
(-)-NopineneChEBI
(-)-Pin-2(10)-eneChEBI
(1S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptaneChEBI
(1S,5S)-beta-PineneChEBI
(1S,5S)-b-PineneGenerator
(1S,5S)-Β-pineneGenerator
(-)-b-PineneGenerator
(-)-Β-pineneGenerator
beta-PineneMeSH
TerbentheneMeSH
TerebentheneMeSH
(-)-(1S,5S)-beta-PineneHMDB
(-)-2(10)-PineneHMDB
(1S)-(-)-beta-PineneHMDB
(1S,5S)-2(10)-PineneHMDB
(1S,5S)-6,6-Dimethyl-2-methylidenebicyclo[3.1.1]heptaneHMDB
(1S,5S)-Pin-2(10)-eneHMDB
1S,5S-(-)-beta-PineneHMDB
L-b-PineneHMDB
laevo-b-PineneHMDB
2(10)-PinenePhytoBank
6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(±)-2(10)-PinenePhytoBank
(±)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(±)-beta-PinenePhytoBank
(±)-β-PinenePhytoBank
NopinenPhytoBank
NopinenePhytoBank
(1S,5S)-(-)-2(10)-PinenePhytoBank
(1S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptanePhytoBank
(-)-(1S)-beta-PinenePhytoBank
(-)-(1S)-β-PinenePhytoBank
(-)-(1S,5S)-β-PinenePhytoBank
(-)-beta-PinenePhytoBank
(1S)-(-)-β-PinenePhytoBank
(1S)-beta-PinenePhytoBank
(1S)-β-PinenePhytoBank
(S)-(-)-beta-PinenePhytoBank
(S)-(-)-β-PinenePhytoBank
(S)-beta-PinenePhytoBank
(S)-β-PinenePhytoBank
l-beta-PinenePhytoBank
l-β-PinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1S,5S)-6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptane
Traditional Name(-)-β-pinene
CAS Registry Number18172-67-3
SMILES
CC1(C)[C@@H]2C[C@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m0/s1
InChI KeyWTARULDDTDQWMU-IUCAKERBSA-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
  • Pinane monoterpenoid
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-61.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.16Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.064 g/LALOGPS
logP3.94ALOGPS
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
Polarizability17.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available132.35131661259
DarkChem[M-H]-PredictedNot Available131.27531661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-30fa40ae82c24567182c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-30fa40ae82c24567182c2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-7a8b637e362b2868237d2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-e26a5aa072ee3c657bb12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-9ce03af98198cbec9a562016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0900000000-83547c837f75972195a62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-ae6e9f2df0d7b06fe3be2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-5e150dd4370565464dad2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-0900000000-45b2edf143e15a1e58672016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-7260f27ae84d64a57ad42021-09-22View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-88790.695 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0-439598.350 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015463
KNApSAcK IDC00000806
Chemspider ID389794
KEGG Compound IDC06307
BioCyc IDCPD-4891
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440967
PDB IDNot Available
ChEBI ID28359
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029858
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uribe S, Rangel P, Pena A: Molecular association enhances the toxic effects of non-substituted monoterpene suspensions on isolated mitochondria. Xenobiotica. 1991 May;21(5):679-88. [PubMed:1949901 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.