2-Oxoadipic acid

2-Oxoadipic acid^[1]

Ball and stick model of α-ketoadipic acid

Names

Preferred IUPAC name

2-Oxohexanedioic acid^[2]

Other names

α-Ketoadipic acid
2-Ketoadipic acid
α-Oxoadipic acid

Identifiers

CAS Number

3184-35-8^Y

3D model (JSmol)

Interactive image
Interactive image

3DMet

B00088

ChEBI

CHEBI:15753^Y

ChemSpider

70^Y

ECHA InfoCard

100.164.320

IUPHAR/BPS

4657

KEGG

C00322^Y

MeSH

Alpha-ketoadipic+acid

PubChem CID

UNII

BB72FKL1M2^Y

CompTox Dashboard (EPA)

DTXSID20185702

InChI

InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)^Y
Key: FGSBNBBHOZHUBO-UHFFFAOYSA-N^Y
InChI=1/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
Key: FGSBNBBHOZHUBO-UHFFFAOYAU

SMILES

C(CC(=O)C(=O)O)CC(=O)O
O=C(C(=O)O)CCCC(=O)O

Properties

Chemical formula

C₆H₈O₅

Molar mass

160.125 g·mol⁻¹

Density

1.4 g cm⁻³

Melting point

125 °C (257 °F; 398 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is ^YN ?)

Infobox references

Chemical compound

2-Oxoadipic acid, also known as α-ketoadipic acid, is an intermediate in the metabolism of lysine and tryptophan.^[3]^[4] The conjugate base and carboxylate is 2-oxoadipate or α-ketoadipate, which is the biochemically relevant form.

References

^ 2-oxoadipate - Compound Summary, PubChem.
^ "Alpha-ketoadipic acid". The PubChem Project. National Center for Biotechnology Information.
^ Voet, Donald; Voet, Judith G. (2011). Biochemistry (4th ed.). Hoboken, NJ: Wiley. pp. 1040–1043. ISBN 978-0-470-57095-1.
^ Dobrota, Dušan (2016). Lekárska biochémia [Medical biochemistry] (in Slovak) (2nd ed.). Martin: Osveta. pp. 329–330, 335–337. ISBN 978-80-8063-444-5.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA