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Human Metabolome Database Version 3.5

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Showing metabocard for L-Dopachrome (HMDB01430)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:33 -0700
HMDB ID HMDB01430
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Dopachrome
Description The non-decarboxylative tautomerization of L-dopachrome to 5,6-dihydroxyindole-2-carboxylic acid in the melanin biosynthetic pathway is catalyzed by Tyrosinase-related protein-2, a melanocyte-specific enzyme. (PMID 11095412 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-L-Carboxy-2,3-dihydroindole-5,6-quinone
  2. L-Dopachrome
Chemical Formula C9H7NO4
Average Molecular Weight 193.1562
Monoisotopic Molecular Weight 193.037507717
IUPAC Name (2S)-5,6-dioxo-2,4,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional IUPAC Name (2S)-5,6-dioxo-2,4-dihydro-1H-indole-2-carboxylic acid
CAS Registry Number 89762-39-0
SMILES OC(=O)[C@H]1NC2=CC(=O)C(=O)CC2=C1
InChI Identifier InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1,3,6,10H,2H2,(H,13,14)/t6-/m0/s1
InChI Key CKZOQLKEDKSKJR-LURJTMIESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteropolycyclic Compounds
Class Cycloalkenes
Sub Class N/A
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Carboxylic Acids
  • Enamines
  • Ketones
  • Pyrrolines
Substituents
  • N/A
Direct Parent Cycloalkenes
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tyrosine metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 11.9 g/L ALOGPS
LogP 0.16 ALOGPS
LogP -0.48 ChemAxon
LogS -1.21 ALOGPS
pKa (strongest acidic) 3.7 ChemAxon
pKa (strongest basic) 1.79 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 83.47 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 47.75 ChemAxon
Polarizability 17.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022618
KNApSAcK ID Not Available
Chemspider ID 17216120 Link_out
KEGG Compound ID C01693 Link_out
BioCyc ID L-DOPACHROME Link_out
BiGG ID 1443253 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01430 Link_out
Metagene Link HMDB01430 Link_out
METLIN ID 6241 Link_out
PubChem Compound 439549 Link_out
PDB ID Not Available
ChEBI ID 15772 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Tyrosinase
Reactions:
  • L-tyrosine + L-dopa + O2 = L-dopa + dopaquinone + H2O [RN:R02078]
Gene Name: TYR
Uniprot ID: P14679 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: L-dopachrome tautomerase
Reactions:
  • L-dopachrome = 5,6-dihydroxyindole-2-carboxylate [RN:R03673]
Gene Name: DCT
Uniprot ID: P40126 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA