Glutaconyl-CoA - Misplaced Pages

Glutaconyl-CoA
Names

IUPAC name (3E)-5-oxy}-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-5-oxopent-3-enoic acid
Systematic IUPAC name (9R,20E)-1--3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14,19-pentaoxo-2,4,6-trioxa-18-thia-11,15-diaza-3λ,5λ-diphosphatricos-20-en-23-oic acid
Other names Glutaconyl-coenzyme A
Identifiers
CAS Number	6712-05-6
3D model (JSmol)	Interactive image
ChemSpider	7822023
MeSH	glutaconyl-coenzyme+A
PubChem CID	9543050
UNII	281DQF1ZC5
InChI InChI=1S/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/b5-3+/t14-,19-,20-,21+,25-/m1/s1Key: URTLOTISFJPPOU-DEGQQWIJSA-N InChI=1/C26H40N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h3,5,12-14,19-21,25,38-39H,4,6-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/b5-3+/t14-,19-,20-,21+,25-/m1/s1Key: URTLOTISFJPPOU-DEGQQWIJBS
SMILES O=C(O)C/C=C/C(=O)SCCNC(=O)CCNC(=O)(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC3O(n2cnc1c(ncnc12)N)(O)3OP(=O)(O)O
Properties
Chemical formula	C₂₆H₄₀N₇O₁₉P₃S
Molar mass	879.62 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Glutaconyl-CoA is an intermediate in the metabolism of lysine. It is an organic compound containing a coenzyme substructure, which classifies it as a fatty ester lipid molecule. Being a lipid makes the molecule hydrophobic, which makes it insoluble in water. The molecule has a molecular formula of C₂₆H₄₀N₇O₁₉P₃S, and a molecular weight 879.62 grams per mole.

Glutaconyl-CoA is postulated to be the main toxin in glutaric aciduria type 1. In certain fermentative bacteria, glutaconyl-CoA decarboxylation is catalyzed by a Na-dependent decarboxylase (EC 7.2.4.5) and is coupled with Na ion translocation, which creates a sodium-motive force as an alternate energy source for these organisms.

References

"Glutaryl-CoA Dehydrogenase - an overview". www.sciencedirect.com. Retrieved 2022-10-18.
"Human Metabolome Database: Showing metabocard for Glutaconyl-CoA (HMDB0001290)". hmdb.ca. Retrieved 2022-10-18.
Lehnert, Willy; Sass, Jörn Oliver (2005-01-01). "Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I)". Medical Hypotheses. 65 (2): 330–333. doi:10.1016/j.mehy.2005.02.021. ISSN 0306-9877. PMID 15922108.
Kress, Daniel; Brügel, Daniela; Schall, Iris; Linder, Dietmar; Buckel, Wolfgang; Essen, Lars-Oliver (October 2009). "An Asymmetric Model for Na+-translocating Glutaconyl-CoA Decarboxylases". Journal of Biological Chemistry. 284 (41): 28401–28409. doi:10.1074/jbc.m109.037762. ISSN 0021-9258. PMC 2788889. PMID 19654317.

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

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

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

This article about an organic compound is a stub. You can help Misplaced Pages by expanding it.

Categories:

See also

References