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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-09-15 18:09:36 UTC
HMDB IDHMDB0001253
Secondary Accession Numbers
  • HMDB01253
Metabolite Identification
Common Name5,6-Dihydroxyindole-2-carboxylic acid
Description5,6-Dihydroxyindole-2-carboxylic acid, also known as DHICA, belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. A dihydroxyindole that is indole-2-carboxylic acid substituted by hydroxy groups at positions 5 and 6. 5,6-Dihydroxyindole-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 5,6-dihydroxyindole-2-carboxylic acid participates in a number of enzymatic reactions. In particular, 5,6-dihydroxyindole-2-carboxylic acid can be biosynthesized from L-dopachrome through its interaction with the enzyme L-dopachrome tautomerase. In addition, 5,6-dihydroxyindole-2-carboxylic acid can be converted into indole-5,6-quinone-2-carboxylate; which is catalyzed by the enzyme tyrosinase. In humans, 5,6-dihydroxyindole-2-carboxylic acid is involved in eumelanin biosynthesis.
Structure
Data?1600193376
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
2-Carboxy-5,6-dihydroxyindoleHMDB
5,6-Dihydroxy-2-carboxyindoleHMDB
5,6-Dihydroxyindole-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=CC(O)=C(O)C=C2N1
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 KeyYFTGOBNOJKXZJC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives 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
  • Pyrrole-2-carboxylic acid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
logP1.11ALOGPS
logP1.04ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)5.11ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.24 m³·mol⁻¹ChemAxon
Polarizability18.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-86e3bb7f8c4c5358f1ef2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00du-5329000000-6168733ed8a73f5699282017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dj-0900000000-4f5bdd6d93d1cff8a09f2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-4323f8e82f9ef2c149e82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-5180e19b4ff79f8ccbe82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-3900000000-523d85a810268dbe9cf72017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6d7269d6d89c3eae16f92017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-0900000000-4d67dcdd279043d446202017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-1900000000-968f54cfbf806d2e23892017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-7937a0f008a0259815162021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-b0b74fab2c882d47700d2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xs-2900000000-a0ec9715df089ba80b982021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b8d69868735567e6ffd72021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0900000000-b28b84208bb53ec6a35b2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-5900000000-f33eeedd7677021f68df2021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022514
KNApSAcK IDNot Available
Chemspider ID106648
KEGG Compound IDC04185
BioCyc ID56-DIHYDROXYINDOLE-2-CARBOXYLATE
BiGG ID1444022
Wikipedia LinkNot Available
METLIN ID6110
PubChem Compound119405
PDB IDNot Available
ChEBI ID2003
Food Biomarker OntologyNot Available
VMH ID56DIHINDLCRBXLT
MarkerDB IDNot Available
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. [PubMed: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. [PubMed: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