ChemFOnt: Showing chemical card for Dopachrome o-semiquinone (CFc000008121)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:46 UTC

Chemfont ID

CFc000008121

Molecule Identification

Common Name

Dopachrome o-semiquinone

Definition

Dopachrome o-semiquinone is the semiquinone derivative of dopachrome. The non-decarboxylative tautomerization of L-dopachrome into 5,6-dihydroxyindole-2-carboxylic acid in the melanin biosynthetic pathway is catalyzed by tyrosinase-related protein-2, a melanocyte-specific enzyme.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
DCSQ	HMDB
Leukodopachrome O-semiquinone radical	HMDB

Chemical Formula

C₉H₈NO₄

Average Molecular Weight

194.1641

Monoisotopic Molecular Weight

194.045332749

IUPAC Name

[(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yl]oxidanyl

Traditional Name

(2R)-2-carboxy-6-hydroxy-2,3-dihydro-1H-indol-5-yloxidanyl

CAS Registry Number

1246035-97-1

SMILES

[O]C1=C(O)C=C2N[C@H](CC2=C1)C(O)=O

InChI Identifier

InChI=1S/C9H8NO4/c11-7-2-4-1-6(9(13)14)10-5(4)3-8(7)12/h2-3,6,10,12H,1H2,(H,13,14)/t6-/m1/s1

InChI Key

YHAPBGUGQAHLME-ZCFIWIBFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group 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

Alternative Parents

Substituents

Indolecarboxylic acid
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Dihydroindole
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Aralkylamine
Benzenoid
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0012931)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	11.4 g/L	ALOGPS
logP	1.1	ALOGPS
logP	0.61	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.9 m³·mol⁻¹	ChemAxon
Polarizability	18.11 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

HMDB0012931

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029211

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Dopachrome o-semiquinone (CFc000008121)

MOL for CFc000008121 (Dopachrome o-semiquinone)

3D MOL for CFc000008121 (Dopachrome o-semiquinone)

3D SDF for CFc000008121 (Dopachrome o-semiquinone)

3D-SDF for CFc000008121 (Dopachrome o-semiquinone)

PDB for CFc000008121 (Dopachrome o-semiquinone)

3D PDB for CFc000008121 (Dopachrome o-semiquinone)

SMILES for CFc000008121 (Dopachrome o-semiquinone)

INCHI for CFc000008121 (Dopachrome o-semiquinone)

Structure for CFc000008121 (Dopachrome o-semiquinone)

3D Structure for CFc000008121 (Dopachrome o-semiquinone)