ChemFOnt: Showing chemical card for L-Dopachrome (CFc000001105)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:40 UTC

Chemfont ID

CFc000001105

Molecule Identification

Common Name

L-Dopachrome

Definition

Dopachrome is a cyclization product of L-DOPA and is an intermediate in the biosynthesis of melanin. Dopaquinone has an ortho-quinone ring, which is known to be neurotoxic and highly reactive with many other compounds (PMID: 413870 ). Dopachrome spontaneously gives rise to 5,6-dihydroxyindole (DHI) or it can be enzymatically metabolized by dopachrome tautomerase to give 5,6-dihydroxyindole-2-carboxylic acid (DHICA). DHI and its oxidation products are also toxic to cells. Many Parkinson's patients are treated with L-DOPA. However, long-term treatment with L-DOPA may actually worsen symptoms or may result in neurotic and psychotic symptoms. These may be due to dopachrome and dopaquinone accumulating in the brain of L-DOPA treated patients (PMID: 19131041 , PMID: 12373519 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-L-Carboxy-2,3-dihydroindole-5,6-quinone	HMDB

Chemical Formula

C₉H₇NO₄

Average Molecular Weight

193.1562

Monoisotopic Molecular Weight

193.037507717

IUPAC Name

(2S)-5,6-dioxo-2,4,5,6-tetrahydro-1H-indole-2-carboxylic acid

Traditional Name

L-dopachrome

CAS Registry Number

89762-39-0

SMILES

[H][C@@]1(NC2=CC(=O)C(=O)CC2=C1)C(O)=O

InChI Identifier

InChI=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 Key

CKZOQLKEDKSKJR-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Indole or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Cyclohexenone
Pyrroline
Vinylogous amide
Ketone
Amino acid
Cyclic ketone
Carboxylic acid
Secondary aliphatic amine
Enamine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Amine
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001430)

Source

Endogenous

Endogenous (HMDB: HMDB0001430)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Eumelanin Biosynthesis (PathBank: SMP0121124)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11.9 g/L	ALOGPS
logP	0.16	ALOGPS
logP	-0.29	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	-8.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.75 m³·mol⁻¹	ChemAxon
Polarizability	17.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022618

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dopachrome

METLIN ID

Not Available

PubChem Compound

439549

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for L-Dopachrome (CFc000001105)

MOL for CFc000001105 (L-Dopachrome)

3D MOL for CFc000001105 (L-Dopachrome)

3D SDF for CFc000001105 (L-Dopachrome)

3D-SDF for CFc000001105 (L-Dopachrome)

PDB for CFc000001105 (L-Dopachrome)

3D PDB for CFc000001105 (L-Dopachrome)

SMILES for CFc000001105 (L-Dopachrome)

INCHI for CFc000001105 (L-Dopachrome)

Structure for CFc000001105 (L-Dopachrome)

3D Structure for CFc000001105 (L-Dopachrome)