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Human Metabolome Database Version 2.5
Showing metabocard for (+)-a-Pinene (HMDB06525)
Legend: enzyme field
| Version | 2.5 | ||||||||||||||||||
| Creation Date | 2007-05-23 15:25:36 | ||||||||||||||||||
| Update Date | 2009-06-05 16:05:15 | ||||||||||||||||||
| Accession Number | HMDB06525 | ||||||||||||||||||
| Secondary Accession Numbers | Not Available | ||||||||||||||||||
| Common Name | (+)-a-Pinene | ||||||||||||||||||
| Description | α-Pinene is an organic compound of the terpene class, one of two isomers of pinene. It is an alkene and it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary (Rosmarinus officinalis). Both enantiomers are known in nature; 1S,5S- or (−)-α-pinene is more common in European pines, whereas the 1R,5R- or (+)-α-isomer is more common in North America. The racemic mixture is present in some oils such as eucalyptus oil. The four-membered ring in α-pinene 1 makes it a reactive hydrocarbon, prone to skeletal rearrangements such as the Wagner-Meerwein rearrangement. For example, attempts to perform hydration or hydrogen halide addition with the alkene functionality typically lead to rearranged products. of under acidic conditions. With concentrated sulfuric acid and ethanol the major products are terpineol 2 and its ethyl ether 3, while glacial acetic acid gives the corresponding acetate ester 4. With dilute acids, terpin hydrate 5 becomes the major product. With one molar equivalent of anhydrous HCl, the simple addition product 6a can be formed at low temperature in the presence of ether, but it is very unstable. At normal temperatures, or if no ether is present, the major product is bornyl chloride 6b, along with a small amount of fenchyl chloride 6c. For many years 6b (also called "artificial camphor") was referred to as "pinene hydrochloride", until it was confirmed as identical with bornyl chloride made from camphene. If more HCl is used, achiral 7 (dipentene hydrochloride) is the major product along with some 6b. Nitrosyl chloride followed by base leads to the oxime 8 which can be reduced to "pinylamine" 9. Both 8 and 9 are stable compounds containing an intact four-membered ring, and these compounds helped greatly in identifying this important component of the pinene skeleton. (Wikipedia) | ||||||||||||||||||
| Synonyms |
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| Chemical IUPAC Name | (1S,5S)-4,7,7-trimethylbicyclo[3.1.1]hept-3-ene | ||||||||||||||||||
| Chemical Formula | C10H16 | ||||||||||||||||||
| Chemical Structure |  |
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| Chemical Taxonomy |
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| Average Molecular Weight | 136.234 | ||||||||||||||||||
| Monoisotopic Molecular Weight | 136.125198 | ||||||||||||||||||
| Isomeric SMILES | CC1=CCC2CC1C2(C)C | ||||||||||||||||||
| Canonical SMILES | CC1=CCC2CC1C2(C)C | ||||||||||||||||||
| KEGG Compound ID | C06306  |
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| BioCyc ID | ALPHA-PINENE-OXIDE |
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| BiGG ID | 47909 |
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| Wikipedia Link | Not Available | ||||||||||||||||||
| NuGOwiki Link | HMDB06525 |
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| Metagene Link | HMDB06525 |
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| METLIN ID | Not Available | ||||||||||||||||||
| PubChem Compound | 82227 |
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| PubChem Substance | 10219259 |
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| ChEBI ID | 28261 |
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| CAS Registry Number | 7785-70-8 | ||||||||||||||||||
| InChI Identifier | InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3 | ||||||||||||||||||
| Synthesis Reference | Not Available | ||||||||||||||||||
| Melting Point (Experimental) | -62 oC | ||||||||||||||||||
| Experimental Water Solubility | Not Available Source: PhysProp | ||||||||||||||||||
| Predicted Water Solubility | 0.00497 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 0.158 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS | ||||||||||||||||||
| Physiological Charge | 0 | ||||||||||||||||||
| State | Liquid | ||||||||||||||||||
| Experimental LogP/Hydrophobicity | 4.44 [GRIFFIN,S ET AL. (1999)] Source: PhysProp | ||||||||||||||||||
| Predicted LogP/Hydrophobicity | 3.66 [Predicted by ALOGPS]; 4.2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS | ||||||||||||||||||
| Material Safety Data Sheet (MSDS) | |||||||||||||||||||
| MOL File | Show |
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| SDF File | Show |
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| PDB File | Show |
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| 2D Structure | |||||||||||||||||||
| 3D Structure | |||||||||||||||||||
| Experimental PDB ID | Not Available | ||||||||||||||||||
| Experimental 1H NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C NMR Spectrum | Not Available | ||||||||||||||||||
| Experimental 13C HSQC Spectrum | Not Available | ||||||||||||||||||
| Predicted 1H NMR Spectrum |
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| Predicted 13C NMR Spectrum |
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| Mass Spectrum | Not Available | ||||||||||||||||||
| Simplified TOCSY Spectrum | Not Available | ||||||||||||||||||
| BMRB Spectrum | Not Available | ||||||||||||||||||
| Cellular Location |
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| 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 |
