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  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL158934  Y
ChemSpider	27618  Y
MeSH	Cysteinyldopa
PubChem CID	29719
UNII	6I8HV27IUT  Y
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) Y Key: SXISMOAILJWTID-UHFFFAOYSA-N Y 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). Y  verify  (what is  YN ?) Infobox references

Cysteinyldopa, or 5-S-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.

See also

• L-DOPA
• D-DOPA

References

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.
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. doi:10.1016/s0021-5155(01)00393-8. PMID   11583680.