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MetaCyc Compound: neurosporaxanthin

Synonyms: β-apo-4'-carotenoic acid, all-trans-neurosporaxanthin

Superclasses: a lipid an isoprenoid a terpenoid a tetraterpenoid a carotenoid a xanthophyll a carotenoate
a secondary metabolite a terpenoid a tetraterpenoid a carotenoid a xanthophyll a carotenoate
an acid all carboxy acids a carboxylate a fatty acid an unsaturated fatty acid a polyunsaturated fatty acid a carotenoate

Citations: [Estrada08]

Chemical Formula: C35H45O2

Molecular Weight: 497.74 Daltons

Monoisotopic Molecular Weight: 498.34978072079997 Daltons

neurosporaxanthin compound structure

SMILES: CC(C=CC=C(C=CC=C(C([O-])=O)C)C)=CC=CC=C(C)C=CC=C(C)C=CC1(C(C)(C)CCCC(C)=1)

InChI: InChI=1S/C35H46O2/c1-27(17-11-19-29(3)21-13-22-32(6)34(36)37)15-9-10-16-28(2)18-12-20-30(4)24-25-33-31(5)23-14-26-35(33,7)8/h9-13,15-22,24-25H,14,23,26H2,1-8H3,(H,36,37)/p-1/b10-9+,17-11+,18-12+,21-13+,25-24+,27-15+,28-16+,29-19+,30-20+,32-22+

InChIKey: InChIKey=UGJYMKZYSUMAKJ-ZGMBEONKSA-M

Unification Links: ChEBI:63069 , KEGG:C08607 , PubChem:50986097

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 587.04834 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

alkane oxidation :
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O

rhizobactin 1021 biosynthesis :
rhizobactin 1021 core + a fatty acid → rhizobactin 1021

saframycin A biosynthesis :
a fatty acid + a holo-[SfmA peptidyl-carrier-protein] + H+ → an acyl-[SfmA peptidyl-carrier-protein] + H2O

Not in pathways:
a fatty acid + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a fatty acid-methyl ester
a fatty acid + a holo-[acyl-carrier protein] + ATP → a 2,3,4-saturated fatty acyl-[acp] + AMP + diphosphate

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

neurosporaxanthin biosynthesis :
apo-4'-lycopenoate → neurosporaxanthin
4'-apo-β-carotenal + NAD+ + H2O → neurosporaxanthin + NADH + 2 H+

acyl-ACP thioesterase pathway :
an acyl-[acyl-carrier protein] + H2O → a fatty acid + a holo-[acyl-carrier protein] + H+

alkane oxidation , fatty acid α-oxidation I :
a fatty aldehyde + NAD+ + H2O → a fatty acid + NADH + 2 H+

ceramide degradation :
a ceramide + H2O → a sphingoid base + a fatty acid

sphingolipid biosynthesis (mammals) , sphingomyelin metabolism :
an N-acyl-sphingosylphosphorylcholine + H2O → a fatty acid + sphingosylphosphorylcholine

sphingosine and sphingosine-1-phosphate metabolism :
a (4E)-sphing-4-enine ceramide + H2O → sphingosine + a fatty acid

the visual cycle I (vertebrates) :
an all-trans-retinyl ester + H2O → 11-cis-retinol + a fatty acid + H+

triacylglycerol degradation :
a 1,2-diglyceride + H2O → a 2-monoglyceride + a fatty acid + H+
a 1-monoglyceride + H2O → a fatty acid + glycerol + H+
a triglyceride + H2O → a 1,2-diglyceride + a fatty acid + H+

Not in pathways:
a 3-(acyloxy)acyl group of bacterial toxin + H2O → a 3-hydroxyacyl group of bacterial toxin + a fatty acid + H+
a steryl-ester + H2O → a fatty acid + a sterol + H+
an L-1-phosphatidylethanolamine[periplasmic space] + H2O[periplasmic space] → a 2-acyl-1-lyso-phosphatidylethanolamine[periplasmic space] + a fatty acid[periplasmic space] + H+[periplasmic space]
a 2-monoglyceride + H2O → glycerol + a fatty acid + H+
an L-1-phosphatidylethanolamine[periplasmic space] + H2O[periplasmic space]a fatty acid[periplasmic space] + a 1-acyl 2-lyso-phosphatidylethanolamine[periplasmic space] + H+[periplasmic space]
a 1,3-diglyceride + H2O → a monoglyceride + a fatty acid
an all-trans-retinyl ester + H2O → 13-cis-retinol + a fatty acid
an 11-cis-retinyl ester + H2O → 11-cis-retinol + a fatty acid
a 1,2-diacyl-sn-glycerol + H2O → a monoglyceride + a fatty acid
an O-acyl-L-carnitine + H2O → L-carnitine + a fatty acid

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

Reactions known to both consume and produce the compound:

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
a fatty acid + hydrogen peroxide = a 3- or 2-hydroxy fatty acid + H2O
a fatty acid + L-alanine + glycine + a holo-[SfmB peptidyl-carrier-protein] + H+ = an acyl-L-alanyl-glycyl-[SfmB peptidyl-carrier-protein] + 3 H2O
a D-glucosyl-N-acylsphingosine + H2O = a fatty acid + O-glucosyl-sphingosine
a 1,2-diacyl-sn-glycerol + H2O = a 1-monoglyceride + a fatty acid + H+
a glycosphingolipid + H2O = a lyso-glycosphingolipid + a fatty acid

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+

Enzymes inhibited by neurosporaxanthin, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 4-hydroxybenzoate-polyprenyltransferase [Kawahara91]

Credits:
Created 15-Dec-2010 by Pujar A , Boyce Thompson Institute


References

Estrada08: Estrada AF, Maier D, Scherzinger D, Avalos J, Al-Babili S (2008). "Novel apocarotenoid intermediates in Neurospora crassa mutants imply a new biosynthetic reaction sequence leading to neurosporaxanthin formation." Fungal Genet Biol 45(11);1497-505. PMID: 18812228

Kawahara91: Kawahara, K., Koizumi, N., Kawaji, H., Oishi, K., Uchida, K. (1991). "Partial Purification and Characterization of 4-Hydroxybenzoate-polyprenyltransferase in Ubiquinone Biosynthesis of Pseudomonas putida." Agricultural and biological chemistry 55(9):2307-2311.

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


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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 Sat Aug 1, 2015, BIOCYC13B.