Human Metabolome Database Version 3.5

Showing metabocard for (+)-Limonene (HMDB04321)

Record Information
Version 3.5
Creation Date 2006-08-13 10:44:29 -0600
Update Date 2013-05-29 13:40:14 -0600
HMDB ID HMDB04321
Secondary Accession Numbers None
Metabolite Identification
Common Name (+)-Limonene
Description Limonene is a monoterpene with a clear colourless liquid at room temperature, a naturally occurring chemical which is the major component in oil of oranges. Limonene is widely used as a flavor and fragrance and is listed to be generally recognized as safe in food by the Food and Drug Administration (21 CFR 182.60 in the Code of Federal Regulations, U.S.A.). Limonene is a botanical (plant-derived) solvent of low toxicity. Mild skin irritation may occur from exposure to limonene and oxidation products of limonene may produce dermal sensitization, and may have irritative and bronchoconstrictive airway effects; however, data are scant and more studies are required. Limonene has been shown to cause a male rat-specific kidney toxicity referred to as hyaline droplet nephropathy. Furthermore, chronic exposure to limonene causes a significant incidence of renal tubular tumors exclusively in male rats. Limonene is one of the active components of dietary phytochemicals that appears to be protective against cancer. (PMID: 16563357 Link_out, 15499193 Link_out, 15325315 Link_out, 2024047 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-(4R)-Limonene
  2. (+)-(R)-Limonene
Chemical Formula C10H16
Average Molecular Weight 136.234
Monoisotopic Molecular Weight 136.125200512
IUPAC Name (4R)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Traditional IUPAC Name (+)-limonene
CAS Registry Number 5989-27-5
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-/m0/s1
InChI Key XMGQYMWWDOXHJM-JTQLQIEISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Monoterpenes
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Menthane monoterpenoids(KEGG)
  • Monoterpenes
  • Terpenoids(KEGG)
  • a limonene(Cyc)
  • monoterpene(ChEBI)
Substituents
  • Cyclohexene
Direct Parent Monocyclic Monoterpenes
Ontology
Status Expected and Not Quantified
Origin
  • Food
Biofunction
  • Cell signaling
  • Component of Monoterpenoid biosynthesis
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -74.3 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.0138 mg/mL at 25 °C Not Available
LogP 4.57 LI,J & PURDUE,EM (1995)
Predicted Properties
Property Value Source
LogP 4.50 ALOGPS
LogP 3.22 ChemAxon
LogS -2.47 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 0 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 46.48 ChemAxon
Polarizability 17.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum EI-B (HITACHI M-80)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB014297
KNApSAcK ID C00010868 Link_out
Chemspider ID 389747 Link_out
KEGG Compound ID C06099 Link_out
BioCyc ID -R-LIMONENE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04321 Link_out
Metagene Link HMDB04321 Link_out
METLIN ID 7051 Link_out
PubChem Compound 440917 Link_out
PDB ID Not Available
ChEBI ID 15382 Link_out
References
Synthesis Reference Sakane, 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) Download (PDF)
General References
  1. Aggarwal BB, Shishodia S: Molecular targets of dietary agents for prevention and therapy of cancer. Biochem Pharmacol. 2006 May 14;71(10):1397-421. Epub 2006 Feb 23. Pubmed: 16563357 Link_out
  2. Tsuda H, Ohshima Y, Nomoto H, Fujita K, Matsuda E, Iigo M, Takasuka N, Moore MA: Cancer prevention by natural compounds. Drug Metab Pharmacokinet. 2004 Aug;19(4):245-63. Pubmed: 15499193 Link_out
  3. DeWitt C, Bebarta V: Botanical solvents. Clin Occup Environ Med. 2004 Aug;4(3):445-54, v-vi. Pubmed: 15325315 Link_out
  4. Flamm WG, Lehman-McKeeman LD: The human relevance of the renal tumor-inducing potential of d-limonene in male rats: implications for risk assessment. Regul Toxicol Pharmacol. 1991 Feb;13(1):70-86. Pubmed: 2024047 Link_out

Enzymes
Name: Cytochrome P450 2C9
Reactions:
(+)-Limonene + NADPH + Oxygen unknown (+)-trans-Carveol + NADP + Water details
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions:
(+)-Limonene + NADPH + Oxygen unknown (+)-trans-Carveol + NADP + Water details
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA