Glutaconyl-CoA: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~265862814~~
			\| Watchedfields = changed
⚫	\|ImageFile=Glutaconyl-coenzyme A.png
		⚫	\| verifiedrevid = 438003154
⚫	\|ImageSize=250px
		⚫	\| ImageFile=Glutaconyl-coenzyme A.png
	\|IUPACName=<small>5-methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethylsulfanyl]-5-oxopent-3-enoic acid</small>
		⚫	\| ImageSize=250px
⚫	\|OtherNames=Glutaconyl-coenzyme A
			\| IUPACName=(3''E'')-5-oxy}-3,3-dimethylbutanamido]propanamido}ethyl)sulfanyl]-5-oxopent-3-enoic acid
			\| SystematicName=(9''R'',20''E'')-1--3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14,19-pentaoxo-2,4,6-trioxa-18-thia-11,15-diaza-3λ<sup>5</sup>,5λ<sup>5</sup>-diphosphatricos-20-en-23-oic acid
		⚫	\| OtherNames=Glutaconyl-coenzyme A
	\|Section1={{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo=6712-05-6		\| CASNo=6712-05-6
⚫	\| PubChem=~~741~~
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| SMILES=CC(C)(COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1) N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)C(C (=O)NCCC(=O)NCCSC(=O)C=CCC(=O)O)O
			\| UNII = 281DQF1ZC5
⚫	\| MeSHName=glutaconyl-coenzyme+A
		⚫	\| PubChem = 9543050
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 7822023
			\| 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
			\| 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/s1
			\| InChIKey = URTLOTISFJPPOU-DEGQQWIJBS
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 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/s1
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = URTLOTISFJPPOU-DEGQQWIJSA-N
		⚫	\| MeSHName=glutaconyl-coenzyme+A
	}}		}}
	\|Section2={{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula=C<sub>26</sub>H<sub>40</sub>N<sub>7</sub>O<sub>19</sub>P<sub>3</sub>S		\| Formula=C<sub>26</sub>H<sub>40</sub>N<sub>7</sub>O<sub>19</sub>P<sub>3</sub>S
	\| MolarMass=879.62 g/mol		\| MolarMass=879.62 g/mol
	\| Appearance=		\| Appearance=
	\| Density=		\| Density=
	\| MeltingPt=		\| MeltingPt=
	\| BoilingPt=		\| BoilingPt=
	\| Solubility=		\| Solubility=
	}}		}}
	\|Section3={{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}

			'''Glutaconyl-CoA''' is an intermediate in the metabolism of ].<ref>{{Cite web \|title=Glutaryl-CoA Dehydrogenase - an overview \|url=https://www.sciencedirect.com/topics/neuroscience/glutaryl-coa-dehydrogenase \|access-date=2022-10-18 \|website=www.sciencedirect.com}}</ref> 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 {{chem2\|C26H40N7O19P3S}}, and a molecular weight 879.62 grams per mole.<ref>{{Cite web \|title=Human Metabolome Database: Showing metabocard for Glutaconyl-CoA (HMDB0001290) \|url=https://hmdb.ca/metabolites/HMDB0001290 \|access-date=2022-10-18 \|website=hmdb.ca}}</ref>
	'''Glutaconyl-CoA''' is an intermediate in the metabolism of ].

			Glutaconyl-CoA is postulated to be the main toxin in ].<ref>{{Cite journal \|last1=Lehnert \|first1=Willy \|last2=Sass \|first2=Jörn Oliver \|date=2005-01-01 \|title=Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I) \|url=https://www.sciencedirect.com/science/article/pii/S0306987705001246 \|journal=Medical Hypotheses \|volume=65 \|issue=2 \|pages=330–333 \|doi=10.1016/j.mehy.2005.02.021 \|pmid=15922108 \|issn=0306-9877}}</ref> In certain fermentative bacteria, glutaconyl-CoA decarboxylation is catalyzed by a ] ({{EnzExplorer\|7.2.4.5}}) and is coupled with Na<sup>+</sup> ion translocation, which creates a ] as an alternate energy source for these organisms.<ref>{{Cite journal \|last1=Kress \|first1=Daniel \|last2=Brügel \|first2=Daniela \|last3=Schall \|first3=Iris \|last4=Linder \|first4=Dietmar \|last5=Buckel \|first5=Wolfgang \|last6=Essen \|first6=Lars-Oliver \|date=October 2009 \|title=An Asymmetric Model for Na+-translocating Glutaconyl-CoA Decarboxylases \|journal=Journal of Biological Chemistry \|volume=284 \|issue=41 \|pages=28401–28409 \|doi=10.1074/jbc.m109.037762 \|doi-access=free \|issn=0021-9258 \|pmc=2788889 \|pmid=19654317}}</ref>

	==See also==		==See also==
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	* ]		* ]

			== References ==
	{{Amino acid metabolism intermediates}}		<references />{{Amino acid metabolism intermediates}}

	]		]


	{{organic-compound-stub}}		{{organic-compound-stub}}

	]

Latest revision as of 00:07, 17 July 2024

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

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Latest revision as of 00:07, 17 July 2024

See also

References