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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:33 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?1676999733
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.79931661259
DarkChem[M-H]-141.99231661259
AllCCS[M+H]+140.86632859911
AllCCS[M-H]-137.52732859911
DeepCCS[M+H]+134.88130932474
DeepCCS[M-H]-132.47230932474
DeepCCS[M-2H]-168.02730932474
DeepCCS[M+Na]+143.56530932474
AllCCS[M+H]+140.932859911
AllCCS[M+H-H2O]+136.532859911
AllCCS[M+NH4]+144.932859911
AllCCS[M+Na]+146.132859911
AllCCS[M-H]-137.532859911
AllCCS[M+Na-2H]-137.632859911
AllCCS[M+HCOO]-137.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,6-Dihydroxyindole-2-carboxylic acidOC(=O)C1=CC2=CC(O)=C(O)C=C2N13573.5Standard polar33892256
5,6-Dihydroxyindole-2-carboxylic acidOC(=O)C1=CC2=CC(O)=C(O)C=C2N12135.1Standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acidOC(=O)C1=CC2=CC(O)=C(O)C=C2N12152.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2[NH]12342.6Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C(C(=O)O)=C22280.4Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C(C(=O)O)[NH]2)C=C1O2286.2Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TMS,isomer #4C[Si](C)(C)N1C(C(=O)O)=CC2=CC(O)=C(O)C=C212323.5Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O)C=C2[NH]12281.4Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C)C=C2[NH]12292.5Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C2337.1Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)[NH]C(C(=O)O)=C22283.2Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C)C(C(=O)O)=C22324.7Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TMS,isomer #6C[Si](C)(C)OC1=CC2=C(C=C1O)C=C(C(=O)O)N2[Si](C)(C)C2321.1Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2[NH]12300.8Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O)C=C2N1[Si](C)(C)C2329.9Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2344.6Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)N([Si](C)(C)C)C(C(=O)O)=C22344.3Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2365.9Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2332.2Standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2N1[Si](C)(C)C2157.7Standard polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2[NH]12617.7Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)[NH]C(C(=O)O)=C22578.5Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C(C(=O)O)[NH]2)C=C1O2583.7Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(C(=O)O)=CC2=CC(O)=C(O)C=C212571.3Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2[NH]12806.5Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]12793.7Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O)C=C2N1[Si](C)(C)C(C)(C)C2770.0Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)[NH]C(C(=O)O)=C22860.2Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C22813.4Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C=C(C(=O)O)N2[Si](C)(C)C(C)(C)C2814.1Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2[NH]13051.2Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2N1[Si](C)(C)C(C)(C)C2967.8Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C2958.5Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C(=O)O)=C23018.9Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C3147.9Semi standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C3131.3Standard non polar33892256
5,6-Dihydroxyindole-2-carboxylic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2N1[Si](C)(C)C(C)(C)C2645.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-86e3bb7f8c4c5358f1ef2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00du-5329000000-6168733ed8a73f5699282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Positive-QTOFsplash10-002f-0900000000-4323f8e82f9ef2c149e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Positive-QTOFsplash10-0002-0900000000-5180e19b4ff79f8ccbe82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Positive-QTOFsplash10-01bc-3900000000-523d85a810268dbe9cf72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Negative-QTOFsplash10-0006-0900000000-6d7269d6d89c3eae16f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Negative-QTOFsplash10-0005-0900000000-4d67dcdd279043d446202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Negative-QTOFsplash10-006t-1900000000-968f54cfbf806d2e23892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Negative-QTOFsplash10-0007-0900000000-7937a0f008a0259815162021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Negative-QTOFsplash10-0002-0900000000-b0b74fab2c882d47700d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Negative-QTOFsplash10-00xs-2900000000-a0ec9715df089ba80b982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 10V, Positive-QTOFsplash10-0006-0900000000-b8d69868735567e6ffd72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 20V, Positive-QTOFsplash10-004l-0900000000-b28b84208bb53ec6a35b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,6-Dihydroxyindole-2-carboxylic acid 40V, Positive-QTOFsplash10-00fu-5900000000-f33eeedd7677021f68df2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
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
Good Scents 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