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Revision as of 14:29, 2 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'StdInChI', 'StdInChIKey').← Previous edit		Latest revision as of 09:54, 7 March 2024 edit undoCitation bot (talk | contribs)Bots5,444,291 edits Add: authors 1-1. Removed proxy/dead URL that duplicated identifier. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Лисан аль-Гаиб | #UCB_webform 122/200
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	{{Chembox		{{Chembox
	| verifiedrevid = 410730450		| verifiedrevid = 458640981
	| ImageFile = Malonyl-CoA2.svg		| ImageFile = Malonyl-CoA2.svg
	| ImageSize =		| ImageSize =
			| PIN = (9''R'')-1--3,5,9-trihydroxy-3,5,10,14,19-pentaoxo-8,8-dimethyl-2,4,6-trioxa-18-thia-11,15-diaza-3λ<sup>5</sup>,5λ<sup>5</sup>-diphosphahenicosan-21-oic acid
	| IUPACName =
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 524-14-1		| CASNo = 524-14-1
			| CASNo_Comment = (free acid)
⚫	| ChemSpiderID = 10213
			| CASNo2 = 116928-84-8
⚫	| StdInChI = 1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19?,23-/m1/s1
			| CASNo2_Comment = (tetralithium salt)
⚫	| StdInChIKey = LTYOQGRJFJAKNA-VFLPNFFSSA-N
			| UNII1_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 869
	| SMILES =		| UNII1 = LNB9YCJ9F9
			| UNII1_Comment = (free acid)
⚫	| MeSHName = Malonyl+CoA
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID = 559121
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChI = 1S/C24H38N7O19P3S/c1-24(2,19(37)22(38)27-4-3-13(32)26-5-6-54-15(35)7-14(33)34)9-47-53(44,45)50-52(42,43)46-8-12-18(49-51(39,40)41)17(36)23(48-12)31-11-30-16-20(25)28-10-29-21(16)31/h10-12,17-19,23,36-37H,3-9H2,1-2H3,(H,26,32)(H,27,38)(H,33,34)(H,42,43)(H,44,45)(H2,25,28,29)(H2,39,40,41)/t12-,17-,18-,19+,23-/m1/s1
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChIKey = LTYOQGRJFJAKNA-DVVLENMVSA-N
		⚫	| PubChem = 644066
			| SMILES =
		⚫	| MeSHName = Malonyl+CoA
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>24</sub>H<sub>38</sub>N<sub>7</sub>O<sub>19</sub>P<sub>3</sub>S		| Formula = C<sub>24</sub>H<sub>38</sub>N<sub>7</sub>O<sub>19</sub>P<sub>3</sub>S
	| MolarMass = 853.582		| MolarMass = 853.582
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPt =		| MeltingPt =
	| BoilingPt =		| BoilingPt =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| Solubility =		| MainHazards =
	| MainHazards =		| FlashPt =
	| FlashPt =		| AutoignitionPt =
	| Autoignition =
	}}		}}
	}}		}}
	'''Malonyl-CoA''' is a ] derivative.		'''Malonyl-CoA''' is a ] derivative of ].
	==Functions==		==Functions==
	It plays a key role in chain elongation in ] biosynthesis and ] biosynthesis.		It plays a key role in chain elongation in ] and ] biosynthesis.
		⚫	=== Cytosolic fatty acid biosynthesis ===
	Malonyl-CoA is also used in transporting ] across the mitochondrial membrane into the mitochondrial matrix.
		⚫	Malonyl-CoA provides 2-carbon units to fatty acids and commits them to fatty acid chain synthesis.
		⚫	Malonyl-CoA is formed by carboxylating ] using the enzyme ]. One molecule of acetyl-CoA joins with a molecule of ],<ref>{{cite book |vauthors=Nelson D, Cox M |year=2008 |title=Lehninger principles of biochemistry |edition=5th |page=806}}</ref> requiring energy rendered from ].
⚫	===Fatty acid biosynthesis===
⚫	In the former, it provides 2-carbon units to fatty acids and commits them to fatty acid chain synthesis.
		⚫	Malonyl-CoA is utilised in fatty acid biosynthesis by the enzyme ] (MCAT). MCAT serves to transfer ] from malonyl-CoA to the terminal ] of ''holo''-] (ACP).
⚫	Malonyl-CoA is formed by carboxylating ] using the enzyme ]. One molecule of acetyl-CoA joins with a molecule of ]<ref>Nelson D, Cox M (2008) Lehninger principles of biochemistry. 5th Ed: pg. 806</ref>, requiring energy rendered from ].
			=== Mitochondrial fatty acid synthesis ===
⚫	Malonyl-CoA is utilised in fatty acid biosynthesis by the enzyme '''malonyl coenzyme A:] transacylase''' (MCAT). MCAT serves to transfer ] from malonyl-CoA to the terminal ] of ''holo''-] (ACP).
			Malonyl-CoA is formed in the first step of ] fatty acid synthesis (mtFASII) from ] by malonyl-CoA synthetase ('']'').<ref name=":1" /><ref>{{Cite journal |last1=Bowman |first1=Caitlyn E. |last2=Rodriguez |first2=Susana |last3=Selen Alpergin |first3=Ebru S. |last4=Acoba |first4=Michelle G. |last5=Zhao |first5=Liang |last6=Hartung |first6=Thomas |last7=Claypool |first7=Steven M. |last8=Watkins |first8=Paul A. |last9=Wolfgang |first9=Michael J. |date=2017 |title=The Mammalian Malonyl-CoA Synthetase ACSF3 Is Required for Mitochondrial Protein Malonylation and Metabolic Efficiency |journal=Cell Chemical Biology |language=en |volume=24 |issue=6 |pages=673–684.e4 |doi=10.1016/j.chembiol.2017.04.009 |pmc=5482780 |pmid=28479296}}</ref>
	===Polyketide biosynthesis===		===Polyketide biosynthesis===
	There is little controversy about the fact that MCAT is also involved in bacterial ] biosynthesis. The fatty acid MCAT together with an acyl carrier protein (ACP), and a polyketide synthase and chain-length factor heterodimer, constitutes the minimal PKS of type II polyketides.		MCAT is also involved in bacterial ] biosynthesis. The enzyme MCAT together with an acyl carrier protein (ACP), and a ] (PKS) and chain-length factor heterodimer, constitutes the minimal PKS of type II polyketides.
	===Regulation===		===Regulation===
	Malonyl-CoA is a highly-regulated molecule in fatty acid synthesis; as such, it inhibits the rate-limiting step in ] of fatty acids. Malonyl CoA inhibits ] from associating with ] by regulating the enzyme carnitine acyltransferase, thereby preventing them from entering the ] where ] and degradation occur.		Malonyl-CoA is a highly regulated molecule in fatty acid synthesis; as such, it inhibits the rate-limiting step in ] of fatty acids. Malonyl-CoA inhibits ] from associating with ] by regulating the enzyme ], thereby preventing them from entering the ], where ] and degradation occur.
			== Related diseases ==
			Malonyl-CoA plays a special role in the mitochondrial clearance of toxic malonic acid in the metabolic disorder ] (CMAMMA).<ref name=":0">{{Cite journal |last1=Bowman |first1=Caitlyn E. |last2=Wolfgang |first2=Michael J. |date=January 2019 |title=Role of the malonyl-CoA synthetase ACSF3 in mitochondrial metabolism |journal=Advances in Biological Regulation |volume=71 |pages=34–40 |doi=10.1016/j.jbior.2018.09.002 |pmc=6347522 |pmid=30201289}}</ref> In CMAMMA due to ACSF3, malonyl-CoA synthetase is decreased, which can generate malonyl-CoA from malonic acid, which can then be converted to acetyl-CoA by ].<ref name=":1">{{Cite journal |last1=Witkowski |first1=Andrzej |last2=Thweatt |first2=Jennifer |last3=Smith |first3=Stuart |date=September 2011 |title=Mammalian ACSF3 Protein Is a Malonyl-CoA Synthetase That Supplies the Chain Extender Units for Mitochondrial Fatty Acid Synthesis |journal=Journal of Biological Chemistry |volume=286 |issue=39 |pages=33729–33736 |doi=10.1074/jbc.M111.291591 |issn=0021-9258 |pmc=3190830 |pmid=21846720 |doi-access=free}}</ref><ref name=":0" /> In contrast, in CMAMMA due to ], malonyl-CoA decarboxylase is decreased, which converts malonyl-CoA to acetyl-CoA.<ref name=":0" />
			<math>\mathrm{Malonic\ acid + CoA + ATP\ \xrightarrow{Malonyl{-}CoA\ Synthetase} \ Malonyl{-}CoA \ \xrightarrow{Malonyl-CoA\ Decarboxylase} \ Acetyl{-}CoA }</math>
	==See also==		==See also==
			*]
	*]
	*]
	==References==		==References==
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	{{DEFAULTSORT:Malonyl-Coa}}		{{DEFAULTSORT:Malonyl-Coa}}
	]		]
	]		]
	]
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	]
	]