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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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 :
zeaxanthin + a reduced electron acceptor + oxygen → adonixanthin + an oxidized electron acceptor + H2O + 2 H+

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

crocetin biosynthesis :
zeaxanthin[chloroplast stroma] + 2 oxygen[chloroplast stroma] → crocetin dialdehyde[chloroplast stroma] + 2 (3S)-3-hydroxycyclocitral[chloroplast stroma]

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 NAD(P)H + 2 H+ + 2 oxygen → violaxanthin + 2 NAD(P)+ + 2 H2O
zeaxanthin + 2 NADH + 2 H+ + 2 oxygen → nostoxanthin + 2 NAD+ + 2 H2O

linoleate biosynthesis I (plants) :
oleoyl-CoA + a lipid + H+ → a lipid oleoyl-group + coenzyme A

Reactions known to produce the compound:

astaxanthin biosynthesis , 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

glutathione redox reactions I :
a lipid hydroperoxide + 2 glutathione + H+a lipid + glutathione disulfide + 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 18.5 on Tue Nov 25, 2014, BIOCYC13B.