ChemFOnt: Showing chemical card for 2-Amino-3-carboxymuconic acid semialdehyde (CFc000001026)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:34 UTC

Chemfont ID

CFc000001026

Molecule Identification

Common Name

2-Amino-3-carboxymuconic acid semialdehyde

Definition

2-Amino-3-carboxymuconic acid semialdehyde (CAS: 16597-58-3) is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic acid semialdehyde is enzymatically converted into 2-aminomuconate via 2-aminomuconic semialdehyde (PMID: 10510494 , 16267312 , 14275129 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-3-carboxymuconate semialdehyde	Generator

Chemical Formula

C₇H₇NO₅

Average Molecular Weight

185.1342

Monoisotopic Molecular Weight

185.032422339

IUPAC Name

2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

Traditional Name

2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid

CAS Registry Number

16597-19-6

SMILES

NC(C(O)=O)=C(C=CC=O)C(O)=O

InChI Identifier

InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)

InChI Key

KACPVQQHDVBVFC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Fatty acyl
Vinylogous amide
Alpha,beta-unsaturated aldehyde
Enal
Amino acid
Carboxylic acid
Enamine
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Aldehyde
Primary amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

amino dicarboxylic acid (CHEBI:19448 )
non-proteinogenic alpha-amino acid (CHEBI:19448 )
oxo dicarboxylic acid (CHEBI:19448 )
muconic semialdehyde (CHEBI:19448 )

Functional Ontology

Not Available

Cellular substructure

Cytoplasm (HMDB: HMDB0001330)

Source

Endogenous

Endogenous (HMDB: HMDB0001330)

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)
NAD Metabolism (PathBank: SMP0002338)
2-Amino-3-Carboxymuconate Semialdehyde Degradation (PathBank: SMP0121131)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.64 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	-3.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	6.72	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.62 m³·mol⁻¹	ChemAxon
Polarizability	16.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

FDB022559

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

PDB ID

Not Available

ChEBI ID

19448

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-Amino-3-carboxymuconic acid semialdehyde (CFc000001026)

MOL for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

3D MOL for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

3D SDF for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

3D-SDF for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

PDB for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

3D PDB for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

SMILES for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

INCHI for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

Structure for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)

3D Structure for CFc000001026 (2-Amino-3-carboxymuconic acid semialdehyde)