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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:07 UTC
HMDB IDHMDB01253
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,6-Dihydroxyindole-2-carboxylic acid
Description5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.
Structure
Thumb
Synonyms
ValueSource
5,6-DHICAChEBI
5,6-Dihydroxy-2-indolecarboxylic acidChEBI
5,6-Dihydroxy-2-indolylcarboxylic acidChEBI
5,6-Dihydroxyindole-2-carboxylateChEBI
DHI2cChEBI
DHICAChEBI
5,6-Dihydroxy-2-indolecarboxylateGenerator
5,6-Dihydroxy-2-indolylcarboxylateGenerator
5,6-Dihydroxy-1H-indole-2-carboxylateHMDB
5,6-Dihydroxy-1H-indole-2-carboxylic acidHMDB
Chemical FormulaC9H7NO4
Average Molecular Weight193.1562
Monoisotopic Molecular Weight193.037507717
IUPAC Name5,6-dihydroxy-1H-indole-2-carboxylic acid
Traditional Namedhica
CAS Registry Number4790-08-3
SMILES
OC(=O)C1=CC2=C(N1)C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1-3,10-12H,(H,13,14)
InChI KeyInChIKey=YFTGOBNOJKXZJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
  • Hydroxyindole
  • Indole
  • Pyrrole-2-carboxylic acid or derivatives
  • Pyrrole-2-carboxylic acid
  • 1,2-diphenol
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.31 mg/mLALOGPS
logP1.11ALOGPS
logP1.04ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.55 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.24 m3·mol-1ChemAxon
Polarizability18.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
AlkaptonuriaSMP00169Not Available
Disulfiram PathwaySMP00429Not Available
Dopamine beta-hydroxylase deficiencySMP00498Not Available
HawkinsinuriaSMP00190Not Available
Monoamine oxidase-a deficiency (MAO-A)SMP00533Not Available
Tyrosine MetabolismSMP00006map00350
Tyrosinemia Type ISMP00218Not Available
Tyrosinemia, transient, of the newbornSMP00494Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022514
KNApSAcK IDNot Available
Chemspider ID106648
KEGG Compound IDC04185
BioCyc ID56-DIHYDROXYINDOLE-2-CARBOXYLATE
BiGG ID1444022
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01253
Metagene LinkHMDB01253
METLIN ID6110
PubChem Compound119405
PDB IDNot Available
ChEBI ID2003
References
Synthesis ReferenceChioccara, Francesco; Novellino, Ettore. Biomimetic synthesis of 5,6-dihydroxyindole-2-carboxylic acid and of its benzyl ester. Synthetic Communications (1987), 17(15), 1815-21.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hansson C: Some indolic compounds as markers of the melanocyte activity. Acta Derm Venereol Suppl (Stockh). 1988;138:1-60. [3176811 ]
  2. Yamada K, Walsh N, Hara H, Jimbow K, Chen H, Ito S: Measurement of eumelanin precursor metabolites in the urine as a new marker for melanoma metastases. Arch Dermatol. 1992 Apr;128(4):491-4. [1580656 ]

Enzymes

General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:
DCT
Uniprot ID:
P40126
Molecular weight:
62928.215
Reactions
L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic aciddetails
General function:
Involved in copper ion binding
Specific function:
Oxidation of 5,6-dihydroxyindole-2-carboxylic acid (DHICA) into indole-5,6-quinone-2-carboxylic acid. May regulate or influence the type of melanin synthesized
Gene Name:
TYRP1
Uniprot ID:
P17643
Molecular weight:
60723.8