ChemFOnt: Showing chemical card for 5,6-Dihydroxyindole-2-carboxylic acid (CFc000000968)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:30 UTC

Chemfont ID

CFc000000968

Molecule Identification

Common Name

5,6-Dihydroxyindole-2-carboxylic acid

Definition

5,6-Dihydroxyindole-2-carboxylic acid is an intermediate in the metabolism of Tyrosine. It is a substrate for Dopachrome tautomerase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5,6-DHICA	ChEBI
5,6-Dihydroxy-2-indolecarboxylic acid	ChEBI
5,6-Dihydroxy-2-indolylcarboxylic acid	ChEBI
5,6-Dihydroxyindole-2-carboxylate	ChEBI
DHI2c	ChEBI
DHICA	ChEBI
5,6-Dihydroxy-2-indolecarboxylate	Generator
5,6-Dihydroxy-2-indolylcarboxylate	Generator
5,6-Dihydroxy-1H-indole-2-carboxylate	HMDB
5,6-Dihydroxy-1H-indole-2-carboxylic acid	HMDB
2-Carboxy-5,6-dihydroxyindole	HMDB
5,6-Dihydroxy-2-carboxyindole	HMDB
5,6-Dihydroxyindole-2-carboxylic acid	HMDB

Chemical Formula

C₉H₇NO₄

Average Molecular Weight

193.1562

Monoisotopic Molecular Weight

193.037507717

IUPAC Name

5,6-dihydroxy-1H-indole-2-carboxylic acid

Traditional Name

dhica

CAS Registry Number

4790-08-3

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 Key

YFTGOBNOJKXZJC-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyindole (CHEBI:2003 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0001253)

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)
Tyrosine Metabolism (HMDB: HMDB0001253)
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 (HMDB: HMDB0001253)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.31 g/L	ALOGPS
logP	1.11	ALOGPS
logP	1.04	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	5.11	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	93.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.24 m³·mol⁻¹	ChemAxon
Polarizability	18.17 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

HMDB0001253

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022514

KNApSAcK ID

Not Available

Chemspider ID

106648

KEGG Compound ID

C04185

BioCyc ID

56-DIHYDROXYINDOLE-2-CARBOXYLATE

BiGG ID

1444022

Wikipedia Link

Not Available

METLIN ID

6110

PubChem Compound

119405

PDB ID

Not Available

ChEBI ID

2003

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Chioccara, Francesco; Novellino, Ettore. Biomimetic synthesis of 5,6-dihydroxyindole-2-carboxylic acid and of its benzyl ester. Synthetic Communications (1987), 17(15), 1815-21.

Showing chemical card for 5,6-Dihydroxyindole-2-carboxylic acid (CFc000000968)

MOL for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

3D MOL for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

3D SDF for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

3D-SDF for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

PDB for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

3D PDB for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

SMILES for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

INCHI for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

Structure for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)

3D Structure for CFc000000968 (5,6-Dihydroxyindole-2-carboxylic acid)