Cysteinyldopa - Misplaced Pages

Cysteinyldopa
Names

IUPAC name 2-Amino-3--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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Cysteinyldopa, or 5-S-cysteinyldopa, is a catecholamine. Excessive cysteinyldopa in plasma and urine has been linked to malignant melanoma. 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.{{cite journal}}: 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. doi:10.1016/s0021-5155(01)00393-8. PMID 11583680.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Neurotransmitter metabolic intermediates

Catecholamines

Anabolism

Phenylalanine → Tyrosine → DOPA (levodopa) → Dopamine → Norepinephrine → Epinephrine

Catabolism

Dopamine	3,4-Dihydroxyphenylacetaldehyde (DOPAL) 3,4-Dihydroxyphenylacetic acid (DOPAC) Homovanillyl alcohol Hydroxytyrosol (3,4-dihydroxyphenylethanol; DOPET) 3-Methoxytyramine (3-MT) Homovanillic acid (HVA)
Norepinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) 3,4-Dihydroxymandelic acid (DHMA) Normetanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL) Vanillylmandelic acid (VMA) 3,4-Dihydroxyphenylethylene glycol (DOPEG, DHPG) 3-Methoxy-4-hydroxyphenylglycol (MHPG, MOPEG)
Epinephrine	3,4-Dihydroxyphenylglycolaldehyde (DOPEGAL, DHMAL) Metanephrine 3-Methoxy-4-hydroxymandelaldehyde (MHMAL)

Tryptophan→Serotonin

Anabolism	Tryptophan 5-Hydroxytryptophan (5-HTP)
Catabolism	5-Hydroxyindoleacetaldehyde (5-HIAL) 5-Hydroxyindoleacetic acid (5-HIAA) 5-Hydroxytryptophol (5-HTOL)

Serotonin→Melatonin

Trace amines

GABA

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See also

References