Showing Compound Card for alpha-Pinene oxide (CDB000202)

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Record Information
Version1.0
Created at2020-03-18 23:28:34 UTC
Updated at2020-11-18 16:34:55 UTC
CannabisDB IDCDB000202
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Pinene oxide
DescriptionAlpha-pinene oxide has been exploited as an abundant and a cheap terpene substrate and precursor for the biosynthesis of desirable oxygenated terpene derivatives such as limonen. While these can be produced chemically, biosynthesis of oxygenated terpenes is the more desirable process since it proceeds under mild conditions, it does not generate toxic waste and the products can be labelled as ‘natural’. Some Pseudomonads utilized alpha-terpene, beta-pinene and alpha-pinene oxide as their sole carbon source, suggesting that they have an active metabolic pathway to use it. Using alpha-pinene oxide as a substrate, resting cells of Pseudomonas fluorescens NCIMB 11671 produced isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. Another study demonstrated that alpha-pinene oxide was consumed by both Pseudomonas flueoescens and rhodesiae with P. rhodesiae being more efficient in converting alpha-pinene oxide to isonovalal (doi:10.1111/j.1365-2672.2008.03923.x). The enzyme alpha-pinene lyase metabolizes alpha-pine oxide to (Z)-2-methyl-5-isopropylhexa-2,5-dienal ( alpha-Cedrene (PMID: 3667522 ). Alpha-pinene oxide can also be metabolized to carveol then carvone, thujune and borneol. Alpha-pinene oxide was quantified in labdanum oil (0.23%) and detected in formosan juniper, lemon balm, lamb's lettuce, calabash nutmeg, ocotea floribunda and pepper ( Ref:DOI ). Alpha-pinene oxide is also found in cannabis (PMID: 6991645 ).
Structure
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MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H16O
Average Molecular Weight152.24
Monoisotopic Molecular Weight152.1201
IUPAC Name(1R,2S,4R,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^{2,4}]octane
Traditional Name(1R,2S,4R,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^{2,4}]octane
CAS Registry Number38301-46-1
SMILES
C[C@@]12O[C@@H]1C[C@H]1C[C@@H]2C1(C)C
InChI Identifier
InChI=1S/C10H16O/c1-9(2)6-4-7(9)10(3)8(5-6)11-10/h6-8H,4-5H2,1-3H3/t6-,7-,8-,10+/m1/s1
InChI KeyNQFUSWIGRKFAHK-DQUBFYRCSA-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
  • Oxepane
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.77ALOGPS
logP1.98ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.41 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound 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 Compound36690300
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Griffiths ET, Harries PC, Jeffcoat R, Trudgill PW: Purification and properties of alpha-pinene oxide lyase from Nocardia sp. strain P18.3. J Bacteriol. 1987 Nov;169(11):4980-3. doi: 10.1128/jb.169.11.4980-4983.1987. [PubMed:3667522 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]