Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 15:12:32 UTC |
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Update Date | 2022-03-07 02:49:17 UTC |
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HMDB ID | HMDB0003101 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Violaxanthin |
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Description | Violaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662 ). |
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Structure | C\C(\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1 |
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Synonyms | Value | Source |
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(3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol | ChEBI | (3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-BETA,BETA-carotene-3,3'-diol | ChEBI | e 161E | ChEBI | all-trans-Violaxanthin | Kegg | (3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-b,b-carotene-3,3'-diol | Generator | (3S,3's,5R,5'r,6S,6's)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3'-diol | Generator | (3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-b,b-carotene-3,3'-diol | Generator | (3S,5R,6S,3's,5'r,6's)-5,6,5',6'-DIEPOXY-5,6,5',6'-tetrahydro-β,β-carotene-3,3'-diol | Generator | Zeaxanthin diepoxide | HMDB | 5,6:5',6'-Diepoxy-5,5',6,6'- tetrahydro-beta-carotene-3,3'-diol | HMDB | (3S,3’S,5R,5’r,6S,6’s)-5,6:5’,6’-diepoxy-5,5’,6,6’-tetrahydro-β,β-carotene-3,3’-diol | HMDB | all-e-Violaxanthin | HMDB | trans-Violaxanthin | HMDB | 5,6:5′,6′-diepoxy-5,5′,6,6′-tetrahydro-beta-carotene-3,3′-diol | HMDB | 5,6:5′,6′-diepoxy-5,5′,6,6′-tetrahydro-β-carotene-3,3′-diol | HMDB | Violaxanthin | HMDB |
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Chemical Formula | C40H56O4 |
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Average Molecular Weight | 600.884 |
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Monoisotopic Molecular Weight | 600.417860283 |
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IUPAC Name | (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol |
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Traditional Name | violaxanthin |
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CAS Registry Number | 126-29-4 |
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SMILES | C\C(\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C |
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InChI Identifier | InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1 |
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InChI Key | SZCBXWMUOPQSOX-WVJDLNGLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Tetraterpenoids |
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Direct Parent | Xanthophylls |
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Alternative Parents | |
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Substituents | - Xanthophyll
- Oxepane
- Cyclic alcohol
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized | Show more...
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Violaxanthin GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Violaxanthin GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Violaxanthin GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Violaxanthin GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-16 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Violaxanthin GC-MS ("Violaxanthin,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-20 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 10V, Positive-QTOF | splash10-0f89-0032597000-af64159ae48b8e1fa899 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 20V, Positive-QTOF | splash10-02ai-0295531000-02d9985c675cc61fb2a6 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 40V, Positive-QTOF | splash10-03xr-3494200000-f5d8d58d659ed07feca7 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 10V, Negative-QTOF | splash10-0002-0000090000-ced1b1342da183c34f3f | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 20V, Negative-QTOF | splash10-0002-0100090000-01c9d49ff3b710660a47 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 40V, Negative-QTOF | splash10-0002-3700490000-fec974be88afdb5602d9 | 2017-06-28 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 10V, Positive-QTOF | splash10-0f89-0011092000-616fb8bff0a6bcc74ce7 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 20V, Positive-QTOF | splash10-014i-0012290000-b312a11edc7cd7432753 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 40V, Positive-QTOF | splash10-0171-2239430000-8af32ab5bfa67570b0bb | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 10V, Negative-QTOF | splash10-0002-0300090000-43c86f6f93850f3afb14 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 20V, Negative-QTOF | splash10-0002-0101290000-7bc5d7e172bc297a22ef | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Violaxanthin 40V, Negative-QTOF | splash10-0002-0315190000-efe6c7c2ed7a99c422ba | 2021-09-25 | Wishart Lab | View Spectrum |
| Show more...
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB03460 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB015879 |
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KNApSAcK ID | C00003787 |
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Chemspider ID | 395237 |
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KEGG Compound ID | C08614 |
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BioCyc ID | CPD1F-133 |
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BiGG ID | Not Available |
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Wikipedia Link | Violaxanthin |
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METLIN ID | Not Available |
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PubChem Compound | 448438 |
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PDB ID | Not Available |
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ChEBI ID | 35288 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1588581 |
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References |
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Synthesis Reference | Acemoglu, Murat; Uebelhart, Peter; Rey, Max; Eugster, Conrad Hans. , Zurich, Zurich, Switz. Syntheses of enantiomerically pure violaxanthins and related compounds. Helvetica Chimica Acta (1988), 71(5), 931-56. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed:16211314 ]
- Wehner A, Grasses T, Jahns P: De-epoxidation of violaxanthin in the minor antenna proteins of photosystem II, LHCB4, LHCB5, and LHCB6. J Biol Chem. 2006 Aug 4;281(31):21924-33. Epub 2006 Jun 5. [PubMed:16754673 ]
- Latowski D, Kruk J, Burda K, Skrzynecka-Jaskier M, Kostecka-Gugala A, Strzalka K: Kinetics of violaxanthin de-epoxidation by violaxanthin de-epoxidase, a xanthophyll cycle enzyme, is regulated by membrane fluidity in model lipid bilayers. Eur J Biochem. 2002 Sep;269(18):4656-65. [PubMed:12230579 ]
- Torregrosa-Crespo J, Montero Z, Fuentes JL, Reig Garcia-Galbis M, Garbayo I, Vilchez C, Martinez-Espinosa RM: Exploring the Valuable Carotenoids for the Large-Scale Production by Marine Microorganisms. Mar Drugs. 2018 Jun 8;16(6). pii: md16060203. doi: 10.3390/md16060203. [PubMed:29890662 ]
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