Showing Compound Card for alpha-Phellandrene (CDB000199)

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Record Information
Version1.0
Created at2020-03-18 23:28:27 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000199
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Phellandrene
Descriptionalpha-Phellandrene, also known as menthadiene, is one of two known Phellandrene isomers, α- and β-, which are double-bonded. In α-phellandrene, both double bonds are endocyclic and in β-phellandrene, one of them is exocyclic. alpha-Phellandrene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. p-Menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. alpha-Phellandrene is possibly neutral, insoluble in water, but miscible with ether. alpha-Phellandrene has a mint, spice, and turpentine taste. alpha-Phellandrene is found in highest concentrations in anises, common sages, and ceylon cinnamons and in lower concentrations in peppermints. alpha-Phellandrene has also been detected in dills, fennels, sweet basils, and tarragons. This could make alpha-phellandrene a potential biomarker for the consumption of these foods. The phellandrenes are used in fragrances because of their pleasing aromas. alpha-Phellandrene is one of the monoterpenes found in Cannabis (PMID:6991645 ),
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4S)-p-Mentha-1(6),2-dieneChEBI
(5S)-5-Isopropyl-2-methylcyclohexa-1,3-dieneChEBI
(S)-(+)-alpha-PhellandreneChEBI
(S)-(+)-a-PhellandreneGenerator
(S)-(+)-Α-phellandreneGenerator
(S)-a-PhellandreneGenerator
(S)-Α-phellandreneGenerator
(+)-alpha-PhellandreneHMDB
(4S)-P-Mentha-1,5-dieneHMDB
(5S)-2-Methyl-5-(propan-2-yl)cyclohexa-1,3-dieneHMDB
D-alpha-PhellandreneHMDB
(+)-a-PhellandreneGenerator
(+)-Α-phellandreneGenerator
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(5S)-2-methyl-5-(propan-2-yl)cyclohexa-1,3-diene
Traditional Name(+)-α-phellandrene
CAS Registry Number2243-33-6
SMILES
CC(C)[C@@H]1CC=C(C)C=C1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1
InChI KeyOGLDWXZKYODSOB-JTQLQIEISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

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Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.29ALOGPS
logP3.21ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.82 m³·mol⁻¹ChemAxon
Polarizability17.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-0fe1966be3faee829decSpectrum
Predicted GC-MSalpha-Phellandrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-84435206059b57657bff2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-f16481e876627d7d4bdf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-6993cdda47b7e020b82d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-380abae33f914a4d40012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-099421ca3a157c7e1c712016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-7900000000-58a61cb646aec74939282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000m-9500000000-57eb4e7b936ea365be202021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-9000000000-7265bcee351c38f0f79c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9000000000-0d460f957e928551b42c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-5a30982006f09d04cfc82021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi StarDetected and Quantified0.1 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.14 +/- 0.01 mg/g dry wt
    • David S. Wishart,...
 details
TrainwreckDetected and Quantified0.4 +/- 0.3 mg/g dry wt details
HMDB IDHMDB0034970
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013568
KNApSAcK IDNot Available
Chemspider ID391432
KEGG Compound IDC11391
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443160
PDB IDNot Available
ChEBI ID367
References
General References
  1. 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 ]