You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2014-10-08 15:55:36 UTC |
---|
Update Date | 2022-03-07 03:17:47 UTC |
---|
HMDB ID | HMDB0061838 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | (-)-alpha-Curcumene |
---|
Description | (-)-alpha-Curcumene, also known as (R)-curcumene or L-α-curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (-)-alpha-Curcumene is possibly neutral. |
---|
Structure | C[C@H](CCC=C(C)C)C1=CC=C(C)C=C1 InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(R)-(-)-alpha-Curcumene | ChEBI | (R)-(-)-Curcumene | ChEBI | (R)-Curcumene | ChEBI | 4-[(1R)-1,5-Dimethylhex-4-enyl]-1-methylbenzene | ChEBI | L-alpha-Curcumene | ChEBI | (R)-1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene | Kegg | (R)-(-)-a-Curcumene | Generator | (R)-(-)-Α-curcumene | Generator | L-a-Curcumene | Generator | L-Α-curcumene | Generator | (-)-a-Curcumene | Generator | (-)-Α-curcumene | Generator | (R)-Isomer OF alpha-curcumene | HMDB | 1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene | HMDB | 2-Methyl-6-p-tolyl-2-heptene | HMDB | alpha-Curcumene | HMDB | (S)-Isomer OF alpha-curcumene | HMDB | Ar-curcumene | HMDB |
|
---|
Chemical Formula | C15H22 |
---|
Average Molecular Weight | 202.3352 |
---|
Monoisotopic Molecular Weight | 202.172150704 |
---|
IUPAC Name | 1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene |
---|
Traditional Name | (-)-α-curcumene |
---|
CAS Registry Number | 4176-17-4 |
---|
SMILES | [H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1 |
---|
InChI Identifier | InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m1/s1 |
---|
InChI Key | VMYXUZSZMNBRCN-CQSZACIVSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Sesquiterpenoids |
---|
Direct Parent | Sesquiterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Bisabolane sesquiterpenoid
- Sesquiterpenoid
- P-cymene
- Toluene
- Benzenoid
- Monocyclic benzene moiety
- Aromatic hydrocarbon
- Branched unsaturated hydrocarbon
- Cyclic olefin
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Not Available | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - (-)-alpha-Curcumene GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-4900000000-75e61317c346feecec2e | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (-)-alpha-Curcumene GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Positive-QTOF | splash10-0udi-0290000000-9e5665300d38ccc6c380 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOF | splash10-100r-9840000000-d684318a257bbd05693f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOF | splash10-066r-9400000000-671ed7e91a8152a3dedd | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOF | splash10-0udi-0090000000-49907b25f88bc4223ff5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOF | splash10-0udi-0090000000-78accdf5fb04e051742c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOF | splash10-0ldr-3910000000-0e04f561e347dce60ba2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Positive-QTOF | splash10-014l-7910000000-070594523adb5fcf2590 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOF | splash10-00kf-9300000000-875e64f2a9577f75db09 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOF | splash10-0006-9400000000-8fa08e9b4d33a2cfb93e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOF | splash10-0udi-0090000000-0b1ac00c3b3c6c0a73b9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOF | splash10-0udi-0290000000-a1f573a51214364e1f18 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOF | splash10-0007-6900000000-b097197b38fa1f21c6f1 | 2021-09-24 | Wishart Lab | View Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | Not Available |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB001674 |
---|
KNApSAcK ID | C00011617 |
---|
Chemspider ID | Not Available |
---|
KEGG Compound ID | C09649 |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 442360 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 10225 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Lenfeld J, Motl O, Trka A: Anti-inflammatory activity of extracts from Conyza canadensis. Pharmazie. 1986 Apr;41(4):268-9. [PubMed:3725873 ]
- D'Armas HT, Mootoo BS, Reynolds WF: An unusual sesquiterpene derivative from the Caribbean gorgonian Pseudopterogorgia rigida. J Nat Prod. 2000 Nov;63(11):1593-5. [PubMed:11087620 ]
- Schwob I, Bessiere JM, Dherbomez M, Viano J: Composition and antimicrobial activity of the essential oil of Hypericum coris. Fitoterapia. 2002 Oct;73(6):511-3. [PubMed:12385876 ]
- Antonious GF, Kochhar TS: Zingiberene and curcumene in wild tomato. J Environ Sci Health B. 2003 Jul;38(4):489-500. [PubMed:12856930 ]
- Zhang A, RajanBabu TV: Chiral benzyl centers through asymmetric catalysis. a three-step synthesis of (R)-(-)-alpha-curcumene via asymmetric hydrovinylation. Org Lett. 2004 Sep 2;6(18):3159-61. [PubMed:15330612 ]
- Takigawa H, Kubota H, Sonohara H, Okuda M, Tanaka S, Fujikura Y, Ito S: Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain. Appl Environ Microbiol. 1993 May;59(5):1336-41. [PubMed:16348930 ]
- Mathela CS, Padalia RC, Chanotiya CS: Kanokonyl acetate-rich Indian valerian from northwestern Himalaya. Nat Prod Commun. 2009 Sep;4(9):1253-6. [PubMed:19831039 ]
- Takigawa H, Sugiyama M, Shibuya Y: C(35)-terpenes from Bacillus subtilis KSM 6-10. J Nat Prod. 2010 Feb 26;73(2):204-7. doi: 10.1021/np900705q. [PubMed:20085287 ]
- Joshi RK: Chemical composition of the essential oil of Lepidagathis fasciculata from Bondla forest of Goa, India. Nat Prod Commun. 2013 Aug;8(8):1163-4. [PubMed:24079194 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|