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MetaCyc Compound: zeaxanthin

Synonyms: β,β-carotene-3,3'-diol

Superclasses: a lipid an isoprenoid a terpenoid a tetraterpenoid a carotenoid a xanthophyll
a secondary metabolite a terpenoid a tetraterpenoid a carotenoid a xanthophyll

Chemical Formula: C40H56O2

Molecular Weight: 568.88 Daltons

Monoisotopic Molecular Weight: 568.4280310418 Daltons

zeaxanthin compound structure

SMILES: CC(C=CC=C(C=CC1(C(C)(C)CC(CC=1C)O))C)=CC=CC=C(C=CC=C(C=CC2(=C(CC(CC(C)(C)2)O)C))C)C

InChI: InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1

InChIKey: InChIKey=JKQXZKUSFCKOGQ-QAYBQHTQSA-N

Unification Links: ChEBI:27547 , ChemSpider:4444421 , HMDB:HMDB02789 , KEGG:C06098 , LIPID MAPS:LMPR01070261 , MetaboLights:MTBLC27547 , PubChem:5280899

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 714.0227 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

11-cis-3-hydroxyretinal biosynthesis :
zeaxanthin + oxygen → (3R)-11-cis-3-hydroxyretinal + (3R)-all-trans-3-hydroxyretinal

astaxanthin biosynthesis (bacteria, fungi, algae) :
zeaxanthin + oxygen → adonixanthin + H2O

carotenoid cleavage :
zeaxanthin + 2 oxygen → crocetin dialdehyde + 2 (3S)-3-hydroxycyclocitral
zeaxanthin + 2 oxygen → 2 3-hydroxy-β-ionone + 4,9-dimethyldodeca-2,4,6,8,10-pentaene-1,12-dial

crocetin biosynthesis :
zeaxanthin + oxygen → β-citraurin + (3S)-3-hydroxycyclocitral

nostoxanthin biosynthesis :
zeaxanthin + NADH + oxygen + H+ → caloxanthin + NAD+ + H2O

zeaxanthin, antheraxanthin and violaxanthin interconversion :
zeaxanthin + NAD(P)H + H+ + oxygen → antheraxanthin + NAD(P)+ + H2O

zeaxanthin-β-D-diglucoside biosynthesis :
UDP-α-D-glucose + zeaxanthin → zeaxanthin-β-D-glucoside + UDP + H+

Not in pathways:
zeaxanthin + 2 NADH + 2 H+ + 2 oxygen → nostoxanthin + 2 NAD+ + 2 H2O
zeaxanthin + 2 NAD(P)H + 2 H+ + 2 oxygen → violaxanthin + 2 NAD(P)+ + 2 H2O

Reactions known to produce the compound:

astaxanthin biosynthesis (bacteria, fungi, algae) , echinenone and zeaxanthin biosynthesis (Synechocystis) , zeaxanthin biosynthesis :
β-cryptoxanthin + NADH + oxygen + H+zeaxanthin + NAD+ + H2O

zeaxanthin, antheraxanthin and violaxanthin interconversion :
antheraxanthin + L-ascorbate + H+zeaxanthin + L-dehydro-ascorbate + H2O

Not in pathways:
all-trans-β-carotene + 2 NADH + 2 H+ + 2 oxygen → zeaxanthin + 2 NAD+ + 2 H2O

In Reactions of unknown directionality:

Not in pathways:
violaxanthin + 2 L-ascorbate + 2 H+ = zeaxanthin + 2 L-dehydro-ascorbate + 2 H2O
zeaxanthin + 2 UDP-α-D-glucose = zeaxanthin bis(β-D-glucoside) + 2 UDP + 2 H+


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Tue Jun 30, 2015, BIOCYC13B.