L-Dopachrome (CHEM035218)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:35:10 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035218
Identification
Common NameL-Dopachrome
ClassSmall Molecule
DescriptionThe L-enantiomer of dopachrome.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass193.156 g/mol
Monoisotopic Mass193.038 g/mol
CAS Registry Number89762-39-0
IUPAC Name(2S)-5,6-dioxo-2,3,5,6-tetrahydro-1H-indole-2-carboxylic acid
Traditional NameL-dopachrome
SMILESOC(=O)[C@H]1NC2=CC(=O)C(=O)CC2=C1
InChI IdentifierInChI=1S/C9H7NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h1,3,6,10H,2H2,(H,13,14)/t6-/m0/s1
InChI KeyCKZOQLKEDKSKJR-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-7d241073b22105a8fd50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-323f4bcd8528fb467c2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-7900000000-13c63b10c546db28b452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-7278b78e7703333d1049Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-37fa92b16a4a5557156cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-2900000000-a811e0992f3245b7b855Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-becbc589150d5f7b8591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-96e2a94dd742e6e1937cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-1900000000-1956f467b1b38dab6842Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ae6d437a06113eb43338Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-0900000000-5329f1d5b80270050bbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-8900000000-bfc43ab0afc8b1b28dafSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001430
FooDB IDFDB022618
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDL-DOPACHROME
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDopachrome
Chemspider ID4573572
ChEBI ID15772
PubChem Compound ID5459802
Kegg Compound IDC01693
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pak BJ, Li Q, Kerbel RS, Ben-David Y: TYRP2-mediated resistance to cis-diamminedichloroplatinum (II) in human melanoma cells is independent of tyrosinase and TYRP1 expression and melanin content. Melanoma Res. 2000 Oct;10(5):499-505.
2. Graham DG, Tiffany SM, Vogel FS: The toxicity of melanin precursors. J Invest Dermatol. 1978 Feb;70(2):113-6.
3. Hattoria N, Wanga M, Taka H, Fujimura T, Yoritaka A, Kubo S, Mochizuki H: Toxic effects of dopamine metabolism in Parkinson's disease. Parkinsonism Relat Disord. 2009 Jan;15 Suppl 1:S35-8. doi: 10.1016/S1353-8020(09)70010-0.
4. Kostrzewa RM, Kostrzewa JP, Brus R: Neuroprotective and neurotoxic roles of levodopa (L-DOPA) in neurodegenerative disorders relating to Parkinson's disease. Amino Acids. 2002;23(1-3):57-63. doi: 10.1007/s00726-001-0110-x.