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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-23 14:25:36 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006525
Secondary Accession Numbers
  • HMDB06525
Metabolite Identification
Common Name(+)-alpha-Pinene
Descriptionalpha-Pinene (CAS: 80-56-8) is an organic compound of the terpene class and is one of two isomers of pinene. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature. 1S,5S- or (-)-alpha-pinene is more common in European pines, whereas the 1R,5R- or (+)-alpha-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil (Wikipedia ).
Structure
Data?1582752389
Synonyms
ValueSource
(+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]hept-2-eneChEBI
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneChEBI
(1R,5R)-alpha-PineneChEBI
alpha-Pinene(dextro)ChEBI
(1R,5R)-a-PineneGenerator
(1R,5R)-Α-pineneGenerator
a-Pinene(dextro)Generator
Α-pinene(dextro)Generator
(+)-a-PineneGenerator
(+)-Α-pineneGenerator
(+)-(1R)-alpha-PineneHMDB
(+)-(1R)-α-PineneHMDB
(+)-(1R,5R)-alpha-PineneHMDB
(+)-(1R,5R)-α-PineneHMDB
(+)-2-PineneHMDB
(+)-alpha-PineneHMDB
(1R)-(+)-alpha-PineneHMDB
(1R)-(+)-α-PineneHMDB
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
(1R)-alpha-PineneHMDB
(1R)-α-PineneHMDB
(1R,5R)-(+)-alpha-PineneHMDB
(1R,5R)-(+)-α-PineneHMDB
(R)-(+)-alpha-PineneHMDB
(R)-(+)-α-PineneHMDB
(±)-2-PineneHMDB
(±)-alpha-PineneHMDB
(±)-α-PineneHMDB
2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
2-PineneHMDB
alpha-PineneHMDB
α-PineneHMDB
(1R,5R)-(+)-2-PinenePhytoBank
d-alpha-PinenePhytoBank
d-α-PinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
Traditional Name(+)-α-pinene
CAS Registry Number7785-70-8
SMILES
CC1=CC[C@@H]2C[C@H]1C2(C)C
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1
InChI KeyGRWFGVWFFZKLTI-RKDXNWHRSA-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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-62 °CNot Available
Boiling Point155.00 to 156.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.07 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.44GRIFFIN,S ET AL. (1999)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP3.66ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.22 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
DarkChem[M+H]+131.49231661259
DarkChem[M-H]-130.00831661259
DeepCCS[M+H]+136.39130932474
DeepCCS[M-H]-133.99630932474
DeepCCS[M-2H]-168.35530932474
DeepCCS[M+Na]+142.68730932474
AllCCS[M+H]+127.132859911
AllCCS[M+H-H2O]+122.632859911
AllCCS[M+NH4]+131.432859911
AllCCS[M+Na]+132.632859911
AllCCS[M-H]-132.532859911
AllCCS[M+Na-2H]-134.032859911
AllCCS[M+HCOO]-135.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-alpha-PineneCC1=CC[C@@H]2C[C@H]1C2(C)C1056.4Standard polar33892256
(+)-alpha-PineneCC1=CC[C@@H]2C[C@H]1C2(C)C971.1Standard non polar33892256
(+)-alpha-PineneCC1=CC[C@@H]2C[C@H]1C2(C)C966.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (+)-alpha-Pinene EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (+)-alpha-Pinene EI-B (Non-derivatized)splash10-0006-9100000000-efa1a7d8bd0221192f0d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-alpha-Pinene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-1900000000-7a79889acc60a4543bcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-alpha-Pinene 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 - (+)-alpha-Pinene 10V, Positive-QTOFsplash10-000i-0900000000-89e84f859d8f1f97d5c22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 20V, Positive-QTOFsplash10-000i-0900000000-fb8d56b761aae12a505c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 40V, Positive-QTOFsplash10-00dr-0900000000-bfe7e4ba927cd83956b42016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 10V, Negative-QTOFsplash10-000i-0900000000-5e150dd4370565464dad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 20V, Negative-QTOFsplash10-000i-0900000000-5e150dd4370565464dad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 40V, Negative-QTOFsplash10-00kr-0900000000-b5dcbaea24fd03f1cbf92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 40V, Negative-QTOFsplash10-000i-0900000000-1a368fcdf84da3da6f722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 10V, Positive-QTOFsplash10-000i-0900000000-32bfa268614bcd6c4f812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 20V, Positive-QTOFsplash10-000i-0900000000-32bfa268614bcd6c4f812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-alpha-Pinene 40V, Positive-QTOFsplash10-05fr-0900000000-eb6403ceb156dbbc7ce82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
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 but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-697455.923 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS
details
FecesDetected and Quantified0-422398.0583 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
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 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
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 IDFDB013765
KNApSAcK IDC00034999
Chemspider ID74205
KEGG Compound IDC06306
BioCyc IDCPD-8754
BiGG IDNot Available
Wikipedia LinkAlpha-Pinene
METLIN IDNot Available
PubChem Compound82227
PDB IDNot Available
ChEBI ID28261
Food Biomarker OntologyNot Available
VMH IDAPPNN
MarkerDB IDNot Available
Good Scents IDrw1137311
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]