Cysteinyldopa

Cysteinyldopa[1]
Names
	IUPAC name 2-Amino-3-[3-[(2-amino-3-hydroxy-3-oxopropyl)thio]-4,5-dihydroxyphenyl]propanoic acid
	Other names 5-S-Cysteinyldopa
Identifiers
CAS Number	19641-92-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL158934 ;
ChemSpider	27618 ;
MeSH	Cysteinyldopa
PubChem CID	29719;
UNII	6I8HV27IUT ;
	InChI InChI=1S/C12H16N2O6S/c13-6(11(17)18)1-5-2-8(15)10(16)9(3-5)21-4-7(14)12(19)20/h2-3,6-7,15-16H,1,4,13-14H2,(H,17,18)(H,19,20) Key: SXISMOAILJWTID-UHFFFAOYSA-N ; InChI=1/C12H16N2O6S/c13-6(11(17)18)1-5-2-8(15)10(16)9(3-5)21-4-7(14)12(19)20/h2-3,6-7,15-16H,1,4,13-14H2,(H,17,18)(H,19,20) Key: SXISMOAILJWTID-UHFFFAOYAI;
	SMILES O=C(O)C(N)Cc1cc(SCC(C(=O)O)N)c(O)c(O)c1;
Properties
Chemical formula	C12H16N2O6S
Molar mass	316.33 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Cysteinyldopa is a catecholamine. Excessive cysteinyldopa in plasma and urine has been linked to malignant melanoma.[1][2][3] Cysteinyldopa is found in large amounts in the plasma and urine of patients with malignant melanoma. It is therefore used in the diagnosis of melanoma and for the detection of postoperative metastases. Cysteinyldopa is believed to be formed by the rapid enzymatic hydrolysis of 5-S-glutathionedopa found in melanin-producing cells.

References

Cysteinyldopa - Compound Summary, PubChem.
Agrup G, Agrup P, Andersson T, Hafström L, Hansson C, Jacobsson S, Jönsson PE, Rorsman H, Rosengren AM, Rosengren E (1979). "5 years' experience of 5-S-cysteinyldopa in melanoma diagnosis". Acta Derm Venereol. 59 (5): 381–388. PMID 93360.CS1 maint: multiple names: authors list (link)
Goto H, Usui M, Wakamatsu K, Ito S (2001). "5-S-cysteinyldopa as diagnostic tumor marker for uveal malignant melanoma". Jpn J Ophthalmol. 45 (5): 538–542. PMID 11583680.CS1 maint: multiple names: authors list (link)

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[pubchem-1] Cysteinyldopa - Compound Summary, PubChem.

[2] Agrup G, Agrup P, Andersson T, Hafström L, Hansson C, Jacobsson S, Jönsson PE, Rorsman H, Rosengren AM, Rosengren E (1979). "5 years' experience of 5-S-cysteinyldopa in melanoma diagnosis". Acta Derm Venereol. 59 (5): 381–388. PMID 93360.CS1 maint: multiple names: authors list (link)

[3] Goto H, Usui M, Wakamatsu K, Ito S (2001). "5-S-cysteinyldopa as diagnostic tumor marker for uveal malignant melanoma". Jpn J Ophthalmol. 45 (5): 538–542. PMID 11583680.CS1 maint: multiple names: authors list (link)