2-Amino-3-carboxymuconic semialdehyde

2-Amino-3-carboxymuconic semialdehyde[1][2] is an intermediate in the metabolism of tryptophan in the tryptophan-niacin catabolic pathway. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to 2-aminomuconate via 2-aminomuconic semialdehyde.

2-Amino-3-carboxymuconic semialdehyde
Skeletal formula of 2-amino-3-carboxymuconic semialdehyde
Ball-and-stick model of the 2-amino-3-carboxymuconic semialdehyde molecule as a zwitterion
Names
Preferred IUPAC name
(2Z)-2-Amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • 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)/p-2/b2-1-,5-4- checkY
    Key: KACPVQQHDVBVFC-OIFXTYEKSA-L checkY
  • C(=C/C(=C(\C(=O)O)/N)/C(=O)O)/C=O
Properties
C7H7NO5
Molar mass 185.13 g/mol
Density 1.527 g/mL
Boiling point 389 °C (732 °F; 662 K)
Hazards
Flash point 189 °C (372 °F; 462 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. "UniProt". www.uniprot.org. Retrieved 2022-11-22.
  2. "Human Metabolome Database: Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (HMDB0001330)". hmdb.ca. Retrieved 2022-11-22.


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