ChemFOnt: Showing chemical card for Cinnabarinic acid (CFc000002047)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:50 UTC

Chemfont ID

CFc000002047

Molecule Identification

Common Name

Cinnabarinic acid

Definition

Cinnabarinic acid, also called Cinnabarinate or Cinnavalininate, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Cinnabarinic acid, is and endogenous metabolite arising from tryptophan metabolism. More specifically, it is a relatively obscure and unstable end-product of the tryptophan-kynurenine pathway. It results from the condensation of two molecules of 3-hydroxy-anthranilic acid via the action of catalase (PMID: 35469990 ). Cinnabarinic acid has been found to bind and to act as a partial agonist of type 4 metabotropic glutamate receptors (mGluR4) (PMID: 22311707 ). It also binds to the aryl hydrocarbon receptor (AhR) and can activate the NF-kappaB pathway (PMID: 35469990 ). Levels of Cinnabarinic acid have been found to increase substantially during inflammation induced by lipopolysaccharide (LPS). Cinnabarinic acid appears to have neuroprotective activity (PMID: 22311707 ). Cinnabarinic acid is present in trace amounts in human brain tissue. Interestingly, Cinnabarinic acid levels are reduced in the prefrontal cortex (PFC) of individuals affected by schizophrenia (PMID: 32506121 ). Cinnabarinic acid has been found to be a potent endogenous antipsychotic-like molecule and it has been suggested that reduced Cinnabarinic acid levels in the PFC might contribute to the pathophysiology of schizophrenia (PMID: 32506121 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cinnabarinic acid	Kegg
Cinnabarinate	Generator
Cinnavalininic acid	Generator
2-amino-3-oxo-3H-Phenoxazin-1,9-dicarboxylic acid	HMDB
2-amino-3H-Phenoxazin-one-1,9-dicarboxylic acid	HMDB
2-amino-3-oxo-3H-Phenoxazin-1,9-dicarboxylate	HMDB
2-amino-3H-Phenoxazin-one-1,9-dicarboxylate	HMDB

Chemical Formula

C₁₄H₈N₂O₆

Average Molecular Weight

300.2231

Monoisotopic Molecular Weight

300.038235998

IUPAC Name

2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid

Traditional Name

cinnabarinic acid

CAS Registry Number

606-59-7

SMILES

NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=O

InChI Identifier

InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)

InChI Key

FSBKJYLVDRVPTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Phenoxazines

Direct Parent

Phenoxazines

Alternative Parents

Substituents

Phenoxazine
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Vinylogous amide
Cyclic ketone
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Primary amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenoxazine (CHEBI:3715 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0004078)

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

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004078)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	0.7	ALOGPS
logP	0.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.37	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.9 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	3	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

HMDB0004078

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023302

KNApSAcK ID

Not Available

Chemspider ID

102864

KEGG Compound ID

C05640

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

114918

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cinnabarinic acid (CFc000002047)

MOL for CFc000002047 (Cinnabarinic acid)

3D MOL for CFc000002047 (Cinnabarinic acid)

3D SDF for CFc000002047 (Cinnabarinic acid)

3D-SDF for CFc000002047 (Cinnabarinic acid)

PDB for CFc000002047 (Cinnabarinic acid)

3D PDB for CFc000002047 (Cinnabarinic acid)

SMILES for CFc000002047 (Cinnabarinic acid)

INCHI for CFc000002047 (Cinnabarinic acid)

Structure for CFc000002047 (Cinnabarinic acid)

3D Structure for CFc000002047 (Cinnabarinic acid)