Showing metabocard for 5,6-Dihydroxyindole-2-carboxylic acid (BMDB0001253)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:06 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0001253
Secondary Accession Numbers
  • BMDB01253
Metabolite Identification
Common Name5,6-Dihydroxyindole-2-carboxylic acid
Description5,6-Dihydroxyindole-2-carboxylic acid, also known as 5,6-dihydroxyindole-2-carboxylic acid or 5,6-dihydroxyindole-2-carboxylic acid, 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. 5,6-Dihydroxyindole-2-carboxylic acid is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 5,6-Dihydroxyindole-2-carboxylic acid participates in a number of enzymatic reactions, within cattle. In particular, 5,6-Dihydroxyindole-2-carboxylic acid can be biosynthesized from L-dopachrome; which is mediated by the enzyme L-dopachrome tautomerase. In addition, 5,6-Dihydroxyindole-2-carboxylic acid can be converted into melanin through its interaction with the enzyme tyrosinase. In cattle, 5,6-dihydroxyindole-2-carboxylic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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=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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • 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
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-86e3bb7f8c4c5358f1efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00du-5329000000-6168733ed8a73f569928View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-4323f8e82f9ef2c149e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-5180e19b4ff79f8ccbe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-3900000000-523d85a810268dbe9cf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-6d7269d6d89c3eae16f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-0900000000-4d67dcdd279043d44620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-1900000000-968f54cfbf806d2e2389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-7937a0f008a025981516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-b0b74fab2c882d47700dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xs-2900000000-a0ec9715df089ba80b98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-b8d69868735567e6ffd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0900000000-b28b84208bb53ec6a35bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-5900000000-f33eeedd7677021f68dfView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001253
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. L-dopachrome tautomerase
General function:
Involved in dopachrome isomerase activity
Specific function:
Catalyzes the conversion of L-dopachrome into 5,6-dihydroxyindole-2-carboxylic acid (DHICA). Involved in regulating eumelanin and phaeomelanin levels.
Gene Name:
DCT
Uniprot ID:
Q95119
Molecular weight:
58787.0
Reactions
L-Dopachrome → 5,6-Dihydroxyindole-2-carboxylic aciddetails
Enzyme Details
2. Tyrosinase
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
2 5,6-Dihydroxyindole-2-carboxylic acid + Oxygen → Melanin + Waterdetails