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MetaCyc Compound: L-cystine

Superclasses: an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida non-standard alpha amino acid
an acidall carboxy acidsa carboxylatean amino acidan alpha amino acida non-standard alpha amino acidcystine
an amino acid or its derivativean amino acidan alpha amino acida non-standard alpha amino acid
an amino acid or its derivativean amino acidan alpha amino acida non-standard alpha amino acidcystine

Chemical Formula: C6H12N2O4S2

Molecular Weight: 240.29 Daltons

Monoisotopic Molecular Weight: 242.03949832819998 Daltons

L-cystine compound structure

SMILES: C(C(C(=O)[O-])[N+])SSCC(C([O-])=O)[N+]

InChI: InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

InChIKey: InChIKey=LEVWYRKDKASIDU-IMJSIDKUSA-N

Unification Links: CAS:24645-67-8, ChEBI:35491, HMDB:HMDB00192, KEGG:C01420, MetaboLights:MTBLC35491, PubChem:6992103

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -36.046562Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
L-cystine + H2O → thiocysteine + pyruvate + ammonium
a reduced thioredoxin + L-cystine → an oxidized thioredoxin + 2 L-cysteine

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acidL-homotyrosine + a 2-oxo acid

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

Not in pathways:
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

Not in pathways:
amino acids(n) + H2O → amino acids(n-1) + an α amino acid
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a protein + H2O → a protein + an α amino 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+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasm] + H2O[periplasm]a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-O-(β-D-galactopyranosyl)-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

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

In Reactions of unknown directionality:

Not in pathways:
2 L-cysteine + NAD+ = L-cystine + NADH + H+
L-cystine = 2-aminoprop-2-enoate + thiocysteine + H+
L-cystine + 2 glutathione = glutathione disulfide + 2 L-cysteine

Not in pathways:
cystine = pyrrothine + 3 H2O

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
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[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
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 [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 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+

In Transport reactions:
L-glutamate[cytosol] + L-cystine[extracellular space]L-cystine[cytosol] + L-glutamate[extracellular space],
L-cystine[periplasm] + ATP + H2O → L-cystine[cytosol] + ADP + phosphate + H+,
L-cystine[cytosol]L-cystine[periplasm],
cystine[cytosol]cystine[periplasm]

Enzymes inhibited by L-cystine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: diaminopimelate decarboxylase [White65] Inhibitor (Mechanism unknown) of: aspartate semialdehyde dehydrogenase [Alvarez04]

This compound has been characterized as an alternative substrate of the following enzymes: L-cysteine-S-conjugate thiol-lyase (deaminating; pyruvate-forming), L-cystathione β-lyase, cystathionine β-lyase


References

Alvarez04: Alvarez E, Ramon F, Magan C, Diez E (2004). "L-cystine inhibits aspartate-beta-semialdehyde dehydrogenase by covalently binding to the essential 135Cys of the enzyme." Biochim Biophys Acta 1696(1);23-9. PMID: 14726201

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

White65: White PJ, Kelly B (1965). "Purification and properties of diaminopimelate decarboxylase from Escherichia coli." Biochem J 96;75-84. PMID: 14343156


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
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