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Human Metabolome Database Version 2.5

 

Showing metabocard for Violaxanthin (HMDB03101)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 16:12:32
Update Date 2009-05-05 20:59:30
Accession Number HMDB03101
Secondary Accession Numbers Not Available
Common Name Violaxanthin
Description Xanthophyll; a carotene epoxide that is precursor to capsanthin; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution); 3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as ''violaxanthin cycle''; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis
Synonyms
  1. 9-cis-Violaxanthin
  2. all-trans-Violaxanthin
Chemical IUPAC Name (1R,3S,6S)-6-[18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]hept-6-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Chemical Formula C40H56O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Alcohols
Class
  • Alcohols and Polyols
Sub Class
  • Simple alcohols
Family
  • Plant Metabolite
Species
  • secondary alcohol
  • dialkyl ether
  • alkene
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Exogenous
Average Molecular Weight 600.870
Monoisotopic Molecular Weight 600.417847
Isomeric SMILES CC(C=CC=C(C)C=C[C@@]12O[C@]1(C)CC(O)CC2(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/[C@]12O[C@]1(C)CC(O)CC2(C)C
Canonical SMILES CC(C=CC=C(C)C=CC12OC1(C)CC(O)CC2(C)C)=CC=CC=C(C)C=CC=C(C)C=CC12OC1(C)CC(O)CC2(C)C
KEGG Compound ID C08614 Link Image
BioCyc ID CPD-7196 Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03101 Link Image
Metagene Link HMDB03101 Link Image
METLIN ID 3672 Link Image
PubChem Compound 92096 Link Image
PubChem Substance 586175 Link Image
ChEBI ID Not Available
CAS Registry Number 126-29-4
InChI Identifier InChI=1/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+/m1/s1
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.
Melting Point (Experimental) 208 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.54e-12 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 5.68e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 8.33 [Predicted by ALOGPS]; 6.9 [Predicted by PubChem via XLOGP]; 11.98 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
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 Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
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
  1. 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 Link Image]
  2. Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed Link Image]
  3. 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 Link Image]