Acromelic acid A

Acromelic acid A
Names
IUPAC name
5-[(3S,4S,5S)-5-Carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-oxo-1H-pyridine-2-carboxylic acid
Identifiers
3D model (JSmol)
Abbreviations ACRO A
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C13H14N2O7/c16-9(17)3-6-7(4-14-10(6)13(21)22)5-1-2-8(12(19)20)15-11(5)18/h1-2,6-7,10,14H,3-4H2,(H,15,18)(H,16,17)(H,19,20)(H,21,22)/t6-,7+,10-/m0/s1 checkY
  • Key: CWXNEBSQRIECMV-PJKMHFRUSA-N
  • C1C(C(C(N1)C(=O)O)CC(=O)O)C2=CC=C(NC2=O)C(=O)O
Properties
C13H14N2O7
Molar mass 310.26 g/mol[1]
Density 1.6±0.1 g/cm3 (predicted)[2]
Boiling point 740.5±60.0 °C at 760 mmHg (predicted)[2]
Acidity (pKa) 1.93±0.60 (predicted)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Acromelic acid A (ACRO A) is a toxic compound that is part of a group known as kainoids, characterized by a structure bearing a pyrrolidine dicarboxylic acid, represented by kainic acid.[4] Acromelic acid A has the molecular formula C13H14N2O7. It has been isolated from a Japanese poisonous mushroom, Clitocybe acromelalga.[5] Acromelic acid is responsible for the poisonous aspects of the mushroom because of its potent neuroexcitatory and neurotoxic properties.[6] Ingestion of the Clitocybe acromelalga, causes allodynia which can continue for over a month.[7] The systemic administration of acromelic acid A in rats results in selective loss of interneurons in the lower spinal cord, without causing neuronal damage in the hippocampus and other regions.[8]

  1. ^ "Acromelic acid A". pubchem. National Center for Biotechnology Information. Retrieved 4 March 2024.
  2. ^ a b "acromelic acid A". Chemspider. Royal society of chemistry. Retrieved 4 March 2024.
  3. ^ "acromelic acid A". chemicalbook. Retrieved 4 March 2024.
  4. ^ Furuta, Kyoji; Wang, Guang Xing; Minami, Toshiaki; Nishizawa, Mikio; Ito, Seiji; Suzuki, Masaaki (2004-03-17). "A simple acromelic acid analog potentially useful for receptor photoaffinity labeling and biochemical studies". Tetrahedron Letters. 45 (20): 3933–3936. doi:10.1016/j.tetlet.2004.03.098. ISSN 0040-4039.
  5. ^ Shinozaki, H.; Ishida, M.; Gotoh, Y.; Kwak, S. (1990), Lubec, Gert; Rosenthal, Gerald A. (eds.), "Acromelic acid as a tool for the study of specific neurone damages", Amino Acids: Chemistry, Biology and Medicine, Dordrecht: Springer Netherlands, pp. 281–293, doi:10.1007/978-94-011-2262-7_32, ISBN 978-94-011-2262-7, retrieved 2024-03-04
  6. ^ Yin, Xia; Yang, An-An; Gao, Jin-Ming (2019-05-08). "Mushroom Toxins: Chemistry and Toxicology". Journal of Agricultural and Food Chemistry. 67 (18): 5053–5071. doi:10.1021/acs.jafc.9b00414. ISSN 1520-5118. PMID 30986058. S2CID 116862463.
  7. ^ Cite error: The named reference :3 was invoked but never defined (see the help page).
  8. ^ Tsuji, K.; Nakamura, Y.; Ogata, T.; Mitani, A.; Kataoka, K.; Shibata, T.; Ishida, M.; Shinozaki, H. (1995-09-01). "Neurotoxicity of acromelic acid in cultured neurons from rat spinal cord". Neuroscience. 68 (2): 585–591. doi:10.1016/0306-4522(95)00149-d. ISSN 0306-4522. PMID 7477968. S2CID 45027663.