Showing metabocard for (+)-Limonene (BMDB0004321)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:12 UTC
Update Date2020-04-22 15:13:43 UTC
BMDB IDBMDB0004321
Secondary Accession Numbers
  • BMDB04321
Metabolite Identification
Common Name(+)-Limonene
DescriptionD-Limonene, also known as L-limonen or dipentene, 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. Thus, D-limonene is considered to be an isoprenoid lipid molecule. D-Limonene exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. D-Limonene exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(S)-LimoneneChEBI
(-)-(4S)-LimoneneChEBI
(4S)-1-Methyl-4-isopropenylcyclohex-1-eneChEBI
(4S)-4-Isopropenyl-1-methylcyclohexeneChEBI
(S)-(-)-p-Mentha-1,8-dieneChEBI
(S)-1-Methyl-4-(1-methylethenyl)cyclohexeneChEBI
(S)-p-Mentha-1,8-dieneChEBI
4AlphaH-p-mentha-1,8-dieneChEBI
L-LimonenChEBI
L-LimoneneChEBI
4-Isopropenyl-1-methyl-1-cyclohexeneHMDB
LimoneneHMDB
(+)-LimoneneHMDB
AISA 5203-L (+)limoneneHMDB
DipenteneHMDB
1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
Limonene, (+-)-isomerHMDB
(D)-LimoneneHMDB
4-Mentha-1,8-dieneHMDB
Limonene, (S)-isomerHMDB
Limonene, (R)-isomerHMDB
(R)-(+)-LimoneneHMDB
(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
(+)-(R)-4-Isopropenyl-1-methylcyclohexeneHMDB
(4R)-1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
D-LimoneneHMDB
4 Mentha 1,8 dieneHMDB
D LimoneneHMDB
(-)-alpha-LimoneneHMDB
(-)-Α-limoneneHMDB
(4S)-1-Methyl-4-(1-methylethenyl)cyclohexeneHMDB
(4S)-LimoneneHMDB
(S)-(-)-LimoneneHMDB
(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-eneHMDB
(S)-4-Isopropenyl-1-methyl-1-cyclohexeneHMDB
(S)-LimoneneHMDB
beta-LimoneneHMDB
L-CarveneHMDB
Β-limoneneHMDB
(-)-LimoneneChEBI
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name(4S)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Name(-)-limonene
CAS Registry Number5989-27-5
SMILES
CC(=C)[C@H]1CCC(C)=CC1
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1
InChI KeyXMGQYMWWDOXHJM-SNVBAGLBSA-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
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-74.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0138 mg/mL at 25 °CNot Available
LogP4.57LI,J & PURDUE,EM (1995)
Predicted Properties
PropertyValueSource
logP4.5ALOGPS
logP3.22ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.48 m³·mol⁻¹ChemAxon
Polarizability17.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0173-9100000000-239928f205c8242a700aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-507f7afbc17b7c2556e2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-1a0c62c6971532ab6782View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0173-9100000000-239928f205c8242a700aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-507f7afbc17b7c2556e2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-9100000000-1a0c62c6971532ab6782View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fgo-9200000000-a79c6ccef83c7113ab9fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001c-8900000000-dfd6c14e6a4e49bfc6dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-002f-9000000000-06c43b864c090aaae8aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01t9-9000000000-e5ee54500bc5feda4631View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-5567709cc9ec1c9909dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9600000000-4570df18c5140586d0bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-61312f12f069cd9de75cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-88ada45edfe65d9e7f3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-1192305465e6c746cfa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4900000000-199ee0c6ed49a35bcff4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001a-9400000000-fb09a1cdd4bc09480281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0564-9000000000-dc5effa7f00987fc8567View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-40d99aa482e2ce5a66f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab5621View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-8900000000-d835e92fba2c2a238797View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014l-9100000000-7e8881e736cecb723a2bView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004321
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006329
KNApSAcK IDC00000803
Chemspider ID388386
KEGG Compound IDC00521
BioCyc IDNot Available
BiGG ID47361
Wikipedia LinkLimonene
METLIN ID6911
PubChem Compound439250
PDB IDNot Available
ChEBI ID15383
References
Synthesis ReferenceSakane, Soichi; Fujiwara, Junya; Maruoka, Keiji; Yamamoto, Hisashi. Chiral leaving group: asymmetric synthesis of limonene and bisabolene. Tetrahedron (1986), 42(8), 2193-2201.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available