Record Information
Version1.0
Creation Date2016-09-30 22:45:51 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0001430
Secondary Accession Numbers
  • BMDB01430
Metabolite Identification
Common NameL-Dopachrome
DescriptionL-Dopachrome belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Based on a literature review a small amount of articles have been published on L-Dopachrome.
Structure
Thumb
Synonyms
ValueSource
2-L-Carboxy-2,3-dihydroindole-5,6-quinoneChEBI
(2S)-2,3,5,6-Tetrahydro-5,6-dioxo-1H-indole-2-carboxylic acidHMDB
(2S)-5,6-Dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acidHMDB
L-DopachromeHMDB
Chemical FormulaC9H7NO4
Average Molecular Weight193.158
Monoisotopic Molecular Weight193.037507709
IUPAC Name(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
CAS Registry Number89762-39-0
SMILES
OC(=O)[C@@H]1CC2=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/h2-3,6,10H,1H2,(H,13,14)/t6-/m0/s1
InChI KeyVJNCICVKUHKIIV-LURJTMIESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Indole or derivatives
  • Dihydroindole
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Vinylogous amide
  • Amino acid
  • Ketone
  • Cyclic ketone
  • Carboxylic acid
  • Secondary aliphatic amine
  • Enamine
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.22ALOGPS
logP-0.087ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)-8.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.48 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, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-7d241073b22105a8fd50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-323f4bcd8528fb467c2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-7900000000-13c63b10c546db28b452View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7278b78e7703333d1049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-37fa92b16a4a5557156cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-2900000000-a811e0992f3245b7b855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-becbc589150d5f7b8591View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-96e2a94dd742e6e1937cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-1900000000-1956f467b1b38dab6842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ae6d437a06113eb43338View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0900000000-5329f1d5b80270050bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-8900000000-bfc43ab0afc8b1b28dafView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001430
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022618
KNApSAcK IDNot Available
Chemspider ID4573572
KEGG Compound IDC01693
BioCyc IDL-DOPACHROME
BiGG IDNot Available
Wikipedia LinkDopachrome
METLIN IDNot Available
PubChem Compound5459802
PDB IDNot Available
ChEBI ID15772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cytokine activity
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 (By similarity).
Gene Name:
MIF
Uniprot ID:
P80177
Molecular weight:
12343.0
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
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
L-Dopachrome + Oxygen → 5,6-Dihydroxyindole + Waterdetails