Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||
| Creation Date | 2006-08-13 17:44:29 | ||||||||||||||||||
| Update Date | 2009-05-27 14:28:59 | ||||||||||||||||||
| Accession Number | HMDB04321 | ||||||||||||||||||
| Secondary Accession Numbers | Not Available | ||||||||||||||||||
| 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, 15499193, 15325315, 2024047) | ||||||||||||||||||
| Synonyms |
|
||||||||||||||||||
| Chemical IUPAC Name | (4R)-1-methyl-4-prop-1-en-2-yl-cyclohexene | ||||||||||||||||||
| Chemical Formula | C10H16 | ||||||||||||||||||
| Chemical Structure | |||||||||||||||||||
| Chemical Taxonomy |
|
||||||||||||||||||
| Average Molecular Weight | 136.234 | ||||||||||||||||||
| Monoisotopic Molecular Weight | 136.125198 | ||||||||||||||||||
| Isomeric SMILES | CC(=C)[C@@H]1CCC(C)=CC1 | ||||||||||||||||||
| Canonical SMILES | CC(=C)C1CCC(C)=CC1 | ||||||||||||||||||
| KEGG Compound ID | C06099 ![]() |
||||||||||||||||||
| BioCyc ID | -R-LIMONENE ![]() |
||||||||||||||||||
| BiGG ID | Not Available | ||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB04321 ![]() |
||||||||||||||||||
| Metagene Link | HMDB04321 ![]() |
||||||||||||||||||
| METLIN ID | 7051 ![]() |
||||||||||||||||||
| PubChem Compound | 440917 ![]() |
||||||||||||||||||
| PubChem Substance | 8145134 ![]() |
||||||||||||||||||
| ChEBI ID | 15382 ![]() |
||||||||||||||||||
| CAS Registry Number | 5989-27-5 | ||||||||||||||||||
| InChI Identifier | InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m0/s1 | ||||||||||||||||||
| 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. | ||||||||||||||||||
| Melting Point (Experimental) | -74.3 oC | ||||||||||||||||||
| Experimental Water Solubility | 0.0138 mg/mL at 25 oC [MASSALDI,HA & KING,CJ (1973)] Source: PhysProp | ||||||||||||||||||
| Predicted Water Solubility | 0.45700002 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||
| Physiological Charge | 0 | ||||||||||||||||||
| State | Liquid | ||||||||||||||||||
| Experimental LogP/Hydrophobicity | 4.57 [LI,J & PURDUE,EM (1995)] Source: PhysProp | ||||||||||||||||||
| Predicted LogP/Hydrophobicity | 4.50 [Predicted by ALOGPS]; 3.7 [Predicted by PubChem via XLOGP] Calculated using ALOGPS | ||||||||||||||||||
| Material Safety Data Sheet (MSDS) | |||||||||||||||||||
| MOL File | Show ![]() |
||||||||||||||||||
| SDF File | Show ![]() |
||||||||||||||||||
| PDB File | Show ![]() |
||||||||||||||||||
| 2D Structure | |||||||||||||||||||
| 3D Structure | |||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||
| Experimental 1H NMR Spectrum | Download Spectrum Download FID (Bruker) Show Experimental Conditions ![]() |
||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C HSQC Spectrum | Download Spectrum Download FID (Bruker) Show Experimental Conditions ![]() |
||||||||||||||||||
| Predicted 1H NMR Spectrum |
Show Image Show Peaklist |
||||||||||||||||||
| Predicted 13C NMR Spectrum |
Show Image Show Peaklist |
||||||||||||||||||
| Mass Spectrum |
|
||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location |
|
||||||||||||||||||
| Biofluid Location | Not Available | ||||||||||||||||||
| Tissue Location | Not Available | ||||||||||||||||||
| Concentrations (Normal) | Not Available | ||||||||||||||||||
| Concentrations (Abnormal) | Not Available | ||||||||||||||||||
| Associated Disorders | Not Available | ||||||||||||||||||
| OMIM ID | Not Available | ||||||||||||||||||
| Pathways | Not Available | ||||||||||||||||||
| General References | Not Available | ||||||||||||||||||
| Metabolic Enzymes |
| Enzyme 1 [top] | |||||||
|---|---|---|---|---|---|---|---|
| Enzyme 1 ID | 6324 | ||||||
| Enzyme 1 Name | Cytochrome P450 2C9 | ||||||
| Enzyme 1 Synonyms |
|
||||||
| Enzyme 1 Gene Name | CYP2C9 | ||||||
| Enzyme 1 Protein Sequence |
>Cytochrome P450 2C9
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP PFYQLCFIPV |
||||||
| Enzyme 1 Number of Residues | 490 | ||||||
| Enzyme 1 Molecular Weight | 55627.4 | ||||||
| Enzyme 1 Theoretical pI | 7.99 | ||||||
| Enzyme 1 GO Classification |
|
||||||
| Enzyme 1 General Function | Involved in monooxygenase activity | ||||||
| Enzyme 1 Specific Function | Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S- warfarin, diclofenac, phenytoin, tolbutamide and losartan | ||||||
| Enzyme 1 Pathways | |||||||
| Enzyme 1 Reactions |
|
||||||
| Enzyme 1 Pfam Domain Function |
|
||||||
| Enzyme 1 Signals |
|
||||||
| Enzyme 1 Transmembrane Regions |
|
||||||
| Enzyme 1 Essentiality | Not Available | ||||||
| Enzyme 1 GenBank ID Protein | 32891803 ![]() |
||||||
| Enzyme 1 UniProtKB/Swiss-Prot ID | P11712 ![]() |
||||||
| Enzyme 1 UniProtKB/Swiss-Prot Entry Name | CP2C9_HUMAN ![]() |
||||||
| Enzyme 1 PDB ID | 1R9O ![]() |
||||||
| Enzyme 1 PDB File | Show | ||||||
| Enzyme 1 3D Structure | |||||||
| Enzyme 1 Cellular Location | Not Available | ||||||
| Enzyme 1 Gene Sequence |
>1473 bp
ATGGATTCTCTTGTGGTCCTTGTGCTCTGTCTCTCATGTTTGCTTCTCCTTTCACTCTGG AGACAGAGCTCTGGGAGAGGAAAACTCCCTCCTGGCCCCACTCCTCTCCCAGTGATTGGA AATATCCTACAGATAGGTATTAAGGACATCAGCAAATCCTTAACCAATCTCTCAAAGGTC TATGGCCCTGTGTTCACTCTGTATTTTGGCCTGAAACCCATAGTGGTGCTGCATGGATAT GAAGCAGTGAAGGAAGCCCTGATTGATCTTGGAGAGGAGTTTTCTGGAAGAGGCATTTTC CCACTGGCTGAAAGAGCTAACAGAGGATTTGGAATTGTTTTCAGCAATGGAAAGAAATGG AAGGAGATCCGGCGTTTCTCCCTCATGACGCTGCGGAATTTTGGGATGGGGAAGAGGAGC ATTGAGGACCGTGTTCAAGAGGAAGCCCGCTGCCTTGTGGAGGAGTTGAGAAAAACCAAG GCCTCACCCTGTGATCCCACTTTCATCCTGGGCTGTGCTCCCTGCAATGTGATCTGCTCC ATTATTTTCCATAAACGTTTTGATTATAAAGATCAGCAATTTCTTAACTTAATGGAAAAG TTGAATGAAAACATCAAGATTTTGAGCAGCCCCTGGATCCAGATCTGCAATAATTTTTCT CCTATCATTGATTACTTCCCGGGAACTCACAACAAATTACTTAAAAACGTTGCTTTTATG AAAAGTTATATTTTGGAAAAAGTAAAAGAACACCAAGAATCAATGGACATGAACAACCCT CAGGACTTTATTGATTGCTTCCTGATGAAAATGGAGAAGGAAAAGCACAACCAACCATCT GAATTTACTATTGAAAGCTTGGAAAACACTGCAGTTGACTTGTTTGGAGCTGGGACAGAG ACGACAAGCACAACCCTGAGATATGCTCTCCTTCTCCTGCTGAAGCACCCAGAGGTCACA GCTAAAGTCCAGGAAGAGATTGAACGTGTGATTGGCAGAAACCGGAGCCCCTGCATGCAA GACAGGAGCCACATGCCCTACACAGATGCTGTGGTGCACGAGGTCCAGAGATACATTGAC CTTCTCCCCACCAGCCTGCCCCATGCAGTGACCTGTGACATTAAATTCAGAAACTATCTC ATTCCCAAGGGCACAACCATATTAATTTCCCTGACTTCTGTGCTACATGACAACAAAGAA TTTCCCAACCCAGAGATGTTTGACCCTCATCACTTTCTGGATGAAGGTGGCAATTTTAAG AAAAGTAAATACTTCATGCCTTTCTCAGCAGGAAAACGGATTTGTGTGGGAGAAGCCCTG GCCGGCATGGAGCTGTTTTTATTCCTGACCTCCATTTTACAGAACTTTAACCTGAAATCT CTGGTTGACCCAAAGAACCTTGACACCACTCCAGTTGTCAATGGATTTGCCTCTGTGCCG CCCTTCTACCAGCTGTGCTTCATTCCTGTCTGA |
||||||
| Enzyme 1 GenBank Gene ID | AY341248 ![]() |
||||||
| Enzyme 1 GeneCard ID | CYP2C9 ![]() |
||||||
| Enzyme 1 GenAtlas ID | CYP2C9 ![]() |
||||||
| Enzyme 1 HGNC ID | HGNC:2623 ![]() |
||||||
| Enzyme 1 Chromosome Location | 1 | ||||||
| Enzyme 1 Locus | 10q24 | ||||||
| Enzyme 1 SNPs | SNPJam Report ![]() |
||||||
| Enzyme 1 General References |
|
||||||
| Enzyme 1 Metabolite References | Not Available | ||||||
| Enzyme 2 [top] | |||||||
| Enzyme 2 ID | 6326 | ||||||
| Enzyme 2 Name | Cytochrome P450 2C19 | ||||||
| Enzyme 2 Synonyms |
|
||||||
| Enzyme 2 Gene Name | CYP2C19 | ||||||
| Enzyme 2 Protein Sequence |
>Cytochrome P450 2C19
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP PFYQLCFIPV |
||||||
| Enzyme 2 Number of Residues | 490 | ||||||
| Enzyme 2 Molecular Weight | 55930.5 | ||||||
| Enzyme 2 Theoretical pI | 7.42 | ||||||
| Enzyme 2 GO Classification |
|
||||||
| Enzyme 2 General Function | Involved in monooxygenase activity | ||||||
| Enzyme 2 Specific Function | Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine | ||||||
| Enzyme 2 Pathways | |||||||
| Enzyme 2 Reactions |
|
||||||
| Enzyme 2 Pfam Domain Function |
|
||||||
| Enzyme 2 Signals |
|
||||||
| Enzyme 2 Transmembrane Regions |
|
||||||
| Enzyme 2 Essentiality | Not Available | ||||||
| Enzyme 2 GenBank ID Protein | 181344 ![]() |
||||||
| Enzyme 2 UniProtKB/Swiss-Prot ID | P33261 ![]() |
||||||
| Enzyme 2 UniProtKB/Swiss-Prot Entry Name | CP2CJ_HUMAN ![]() |
||||||
| Enzyme 2 PDB ID | 1R9O ![]() |
||||||
| Enzyme 2 PDB File | Show | ||||||
| Enzyme 2 3D Structure | |||||||
| Enzyme 2 Cellular Location | Not Available | ||||||
| Enzyme 2 Gene Sequence |
>1473 bp
ATGGATCCTTTTGTGGTCCTTGTGCTCTGTCTCTCATGTTTGCTTCTCCTTTCAATCTGG AGACAGAGCTCTGGGAGAGGAAAACTCCCTCCTGGCCCCACTCCTCTCCCAGTGATTGGA AATATCCTACAGATAGATATTAAGGATGTCAGCAAATCCTTAACCAATCTCTCAAAAATC TATGGCCCTGTGTTCACTCTGTATTTTGGCCTGGAACGCATGGTGGTGCTGCATGGATAT GAAGTGGTGAAGGAAGCCCTGATTGATCTTGGAGAGGAGTTTTCTGGAAGAGGCCATTTC CCACTGGCTGAAAGAGCTAACAGAGGATTTGGAATCGTTTTCAGCAATGGAAAGAGATGG AAGGAGATCCGGCGTTTCTCCCTCATGACGCTGCGGAATTTTGGGATGGGGAAGAGGAGC ATTGAGGACCGTGTTCAAGAGGAAGCCCGCTGCCTTGTGGAGGAGTTGAGAAAAACCAAG GCTTCACCCTGTGATCCCACTTTCATCCTGGGCTGTGCTCCCTGCAATGTGATCTGCTCC ATTATTTTCCAGAAACGTTTCGATTATAAAGATCAGCAATTTCTTAACTTGATGGAAAAA TTGAATGAAAACATCAGGATTGTAAGCACCCCCTGGATCCAGATATGCAATAATTTTCCC ACTATCATTGATTATTTCCCGGGAACCCATAACAAATTACTTAAAAACCTTGCTTTTATG GAAAGTGATATTTTGGAGAAAGTAAAAGAACACCAAGAATCGATGGACATCAACAACCCT CGGGACTTTATTGATTGCTTCCTGATCAAAATGGAGAAGGAAAAGCAAAACCAACAGTCT GAATTCACTATTGAAAACTTGGTAATCACTGCAGCTGACTTACTTGGAGCTGGGACAGAG ACAACAAGCACAACCCTGAGATATGCTCTCCTTCTCCTGCTGAAGCACCCAGAGGTCACA GCTAAAGTCCAGGAAGAGATTGAACGTGTCATTGGCAGAAACCGGAGCCCCTGCATGCAG GACAGGGGCCACATGCCCTACACAGATGCTGTGGTGCACGAGGTCCAGAGATACATCGAC CTCATCCCCACCAGCCTGCCCCATGCAGTGACCTGTGACGTTAAATTCAGAAACTACCTC ATTCCCAAGGGCACAACCATATTAACTTCCCTCACTTCTGTGCTACATGACAACAAAGAA TTTCCCAACCCAGAGATGTTTGACCCTCGTCACTTTCTGGATGAAGGTGGAAATTTTAAG AAAAGTAACTACTTCATGCCTTTCTCAGCAGGAAAACGGATTTGTGTGGGAGAGGGCCTG GCCCGCATGGAGCTGTTTTTATTCCTGACCTTCATTTTACAGAACTTTAACCTGAAATCT CTGATTGACCCAAAGGACCTTGACACAACTCCTGTTGTCAATGGATTTGCTTCTGTCCCG CCCTTCTATCAGCTGTGCTTCATTCCTGTCTGA |
||||||
| Enzyme 2 GenBank Gene ID | M61854 ![]() |
||||||
| Enzyme 2 GeneCard ID | CYP2C19 ![]() |
||||||
| Enzyme 2 GenAtlas ID | CYP2C19 ![]() |
||||||
| Enzyme 2 HGNC ID | HGNC:2621 ![]() |
||||||
| Enzyme 2 Chromosome Location | 1 | ||||||
| Enzyme 2 Locus | 10q24.1-q24.3 | ||||||
| Enzyme 2 SNPs | SNPJam Report ![]() |
||||||
| Enzyme 2 General References |
|
||||||
| Enzyme 2 Metabolite References | Not Available | ||||||