acetyl-CoA

• アセチル補酵素A、アセチルコエンザイムA、アセチルCoA、アセチル-CoA

関

acetyl-coenzyme A

WordNet

1. the 3rd letter of the Roman alphabet (同)c
2. (music) the keynote of the scale of C major
3. a general-purpose programing language closely associated with the UNIX operating system
4. the organic group of acetic acid (CH3CO-) (同)acetyl_group, acetyl radical, ethanoyl group, ethanoyl radical

PrepTutorEJDIC

1. carbonの化学記号
2. cobaltの化学記号

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/10/09 11:49:48」(JST)

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[Wiki en表示]

Acetyl-CoA
Identifiers
CAS number	72-89-9 Y
PubChem	444493
ChemSpider	392413 Y
MeSH	Acetyl+Coenzyme+A
ChEBI	CHEBI:15351 Y
Jmol-3D images	Image 1 Image 2
SMILES O=C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O)C CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)OP(=O)(O)O)O
InChI InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Y Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N Y InChI=1/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 Key: ZSLZBFCDCINBPY-ZSJPKINUBJ
Properties
Molecular formula	C23H38N7O17P3S
Molar mass	809.57 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acetyl coenzyme A or acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. Its main function is to convey the carbon atoms within the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production. In chemical structure, acetyl-CoA is the thioester between coenzyme A (a thiol) and acetic acid (an acyl group carrier). Acetyl-CoA is produced during the second step of aerobic cellular respiration, pyruvate decarboxylation, which occurs in the matrix of the mitochondria. Acetyl-CoA then enters the citric acid cycle.

Acetyl-CoA is also an important component in the biogenic synthesis of the neurotransmitter acetylcholine. Choline, in combination with acetyl-CoA, is catalyzed by the enzyme choline acetyltransferase to produce acetylcholine and a coenzyme a byproduct.

Konrad Bloch and Feodor Lynen were awarded the 1964 Nobel Prize in Physiology and Medicine for their discoveries linking acetyl-CoA and fatty acid metabolism.

Functions

Pyruvate dehydrogenase and pyruvate formate lyase reactions

The oxidative conversion of pyruvate into acetyl-CoA is referred to as the pyruvate dehydrogenase reaction. It is catalyzed by the pyruvate dehydrogenase complex. Other conversions between pyruvate and acetyl-CoA are possible. For example, pyruvate formate lyase disproportionates pyruvate into acetyl-CoA and formic acid.

Fatty acid metabolism

In animals, acetyl-CoA is essential to the balance between carbohydrate metabolism and fat metabolism (see fatty acid synthesis). In normal circumstances, acetyl-CoA from fatty acid metabolism feeds into the citric acid cycle, contributing to the cell's energy supply. In the liver, when levels of circulating fatty acids are high, the production of acetyl-CoA from fat breakdown exceeds the cellular energy requirements. To make use of the energy available from the excess acetyl-CoA, ketone bodies are produced, which can then circulate in the blood.

In some circumstances, this can lead to the presence of very high levels of ketone bodies in the blood, a condition called ketosis which is different from ketoacidosis, a dangerous condition that can affect diabetics.

In plants, de novo fatty acid synthesis occurs in the plastids. Many seeds accumulate large reservoirs of seed oils to support germination and early growth of the seedling before it is a net photosynthetic organism. Fatty acids are incorporated into membrane lipids, the major component of most membranes.

Other reactions

• Two acetyl-CoA molecules can be condensed to create acetoacetyl-CoA, the first step in the HMG-CoA/mevalonic acid pathway, leading to synthesis of isoprenoids. In animals, HMG-CoA is a vital precursor to cholesterol and ketone body synthesis.
• Acetyl-CoA is also the source of the acetyl group incorporated onto certain lysine residues of histone and nonhistone proteins in the posttranslational modification acetylation, a reaction catalyzed by acetyltransferases.
• In plants and animals, cytosolic acetyl-CoA is synthesized by ATP citrate lyase. When glucose is abundant in the blood of animals, it is converted via glycolysis in the cytosol to pyruvate, and then to acetyl-CoA in the mitochondrion. The excess of acetyl-CoA results in production of excess citrate, which is exported into the cytosol to give rise to cytosolic acetyl-CoA.
• Acetyl-CoA can be carboxylated in the cytosol by acetyl-CoA carboxylase, giving rise to malonyl-CoA, a substrate required for synthesis of flavonoids and related polyketides, for elongation of fatty acids to produce waxes, cuticle, and seed oils in members of the Brassica family, and for malonation of proteins and other phytochemicals.
• In plants, these include sesquiterpenes, brassinosteroids (hormones), and membrane sterols.

Interactive pathway map

Click on genes, proteins and metabolites below to visit Gene Wiki pages and related Wikipedia articles. The pathway can be downloaded and edited at WikiPathways.

[[File: [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] |{{{bSize}}}px]] Citric_acid_cycle edit

[[File: [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] [[ ]] |{{{bSize}}}px]] Statin Pathway edit

See also

• Citric acid cycle
• HMG-CoA reductase pathway
• Fatty acid metabolism
• Acyl CoA
• Acetyl Co-A synthetase
• Malonyl-CoA decarboxylase

References

External links

• Acetyl+Coenzyme+A at the US National Library of Medicine Medical Subject Headings (MeSH)

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 成人における糖尿病性ケトアシドーシスおよび高浸透圧性高血糖状態：疫学および病因 diabetic ketoacidosis and hyperosmolar hyperglycemic state in adults epidemiology and pathogenesis
• 2. 先天性代謝異常：分類 inborn errors of metabolism classification
• 3. 脂質およびプリン代謝障害による代謝性ミオパチー metabolic myopathies caused by disorders of lipid and purine metabolism
• 4. スタチン誘発性ミオパチー statin myopathy
• 5. 筋肉におけるエネルギー代謝 energy metabolism in muscle

English Journal

• Inhibition of ATP synthesis by fenbufen and its conjugated metabolites in rat liver mitochondria.

• Syed M1, Skonberg C2, Hansen SH3.
• Toxicology in vitro : an international journal published in association with BIBRA.Toxicol In Vitro.2016 Mar;31:23-9. doi: 10.1016/j.tiv.2015.11.013. Epub 2015 Nov 21.
• Fenbufen is an arylpropionic acid derivative belonging to the group of non-steroidal anti-inflammatory drugs (NSAIDs). Even though fenbufen is considered a safe drug, some adverse reactions including hepatic events have been reported. To investigate whether mitochondrial damage could be involved in
• PMID 26612354

• Effects of wintertime fasting and seasonal adaptation on AMPK and ACC in hypothalamus, adipose tissue and liver of the raccoon dog (Nyctereutes procyonoides).

• Kinnunen S1, Mänttäri S2, Herzig KH3, Nieminen P4, Mustonen AM4, Saarela S5.
• Comparative biochemistry and physiology. Part A, Molecular & integrative physiology.Comp Biochem Physiol A Mol Integr Physiol.2016 Feb;192:44-51. doi: 10.1016/j.cbpa.2015.11.010. Epub 2015 Nov 18.
• The raccoon dog (Nyctereutes procyonoides) is a canid with autumnal fattening and passive wintering strategy. We examined the effects of wintertime fasting and seasonality on AMP-activated protein kinase (AMPK), a regulator of metabolism, and its target, acetyl-CoA carboxylase (ACC) on the species.
• PMID 26603554

• Physiological and transcriptional characterization of Saccharomyces cerevisiae engineered for production of fatty acid ethyl esters.

• de Jong BW1, Siewers V2, Nielsen J3.
• FEMS yeast research.FEMS Yeast Res.2016 Feb;16(1). pii: fov105. doi: 10.1093/femsyr/fov105. Epub 2015 Nov 21.
• Saccharomyces cerevisiae has previously been engineered to become a cell factory for the production of fatty acid ethyl esters (FAEEs), molecules suitable for crude diesel replacement. To find new metabolic engineering targets for the improvement of FAEE cell factories, three different FAEE-producin
• PMID 26590613

Japanese Journal

• D-Pantethine Has Vitamin Activity Equivalent to D-Pantothenic Acids for Recovering from a Deficiency of D-Pantothenic Acid in Rats

• SHIBATA Katsumi,KANEKO Mayu,FUKUWATARI Tsutomu
• Journal of Nutritional Science and Vitaminology 59(2), 93-99, 2013
• … The recoveries of body weight, tissue weights, and tissue concentrations of free D-pantothenic acid, dephospho-CoA, CoA, and acetyl-CoA were identical between rats fed diets containing D-pantothenic acid and D-pantethine. …
• NAID 130003368165

• A Comparative Metabolomics Analysis of Saccharopolyspora spinosa WT, WH124, and LU104 Revealed Metabolic Mechanisms Correlated with Increases in Spinosad Yield

• ZHAO Fanglong,XUE Chaoyou,WANG Meiling,WANG Xiaoyang,LU Wenyu
• Bioscience, Biotechnology, and Biochemistry, 2013
• … These biomarkers were associated with central carbon metabolism (succinic acid, α-ketoglutarate, acetyl-CoA, and ATP), amino acid metabolism (glutamate, glutamine, and valine), and secondary metabolism (pseudoaglycone), etc. …
• NAID 130003361177

• Sasa quelpaertensis and p-Coumaric Acid Attenuate Oleic Acid-Induced Lipid Accumulation in HepG2 Cells

• KIM Jeong-Hwan,KANG Seong-Il,SHIN Hye-Sun,YOON Seon-A,KANG Seung-Woo,KO Hee-Chul,KIM Se-Jae
• Bioscience, Biotechnology, and Biochemistry, 2013
• … JBE and CA increased the phosphorylation of AMP-activated protein kinase (AMPK), and acetyl-CoA carboxylase (ACC) and the expression of carnitine palmitoyl transferase 1a (CPT1a) in OA-treated HepG2 cells. …
• NAID 130003361154

Related Links

• アセチルCoA(アセチルコエー)とは - コトバンク

デジタル大辞泉 - アセチルCoAの用語解説 - 《acetyl-CoA》補酵素A（CoA）のチオール基と酢酸のカルボキシル基がチオエステル結合した化合物。高エネルギー化合物の一つ。生体内で糖質・脂質・アミノ酸の代謝や脂肪酸の合成に関与 ...

• Acetyl-CoAとは - goo Wikipedia (ウィキペディア)

Acetyl-CoAとは？goo Wikipedia (ウィキペディア) 。出典：Wikipedia（ウィキペディア）フリー百科事典。 Acetyl-CoAとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへスキップ 本文へ ...

Related Pictures

---

★リンクテーブル★

リンク元	「コレステロール」「解糖系」「ビオチン」「コレステロール生合成」「アセチル補酵素A」
拡張検索	「acetyl-CoA acyltransferase」「acetyl-CoA hydrolase」「acetoacetyl-CoA thiolase deficiency」
関連記事	「C」「CoA」「COA」「acetyl」「Co」

「コレステロール」

　　[★]

英

cholesterol

同

コレステリン cholesterin

関

lipoprotein

• コレステロールは多くの場合、長鎖脂肪酸のコレステロールエステルとして食品に多く含まれる (SP.739)

分子式

• C27H46O = 386.66

吸収

• 小腸から放出された脂質とコレステロールはアポ蛋白とカイロミクロンを形成する。
• カイロミクロンは血液循環に入り、循環中にカイロミクロンレムナント chylomicron remnantとなる。

カイロミクロンに含まれる脂質は、血管内皮に存在するリポ蛋白リパーゼ(LPL)により分解されて脂肪酸を遊離し、コレステロールの比が高いカイロミクロンレムナントとなる。

• 肝臓はカイロミクロンレムナントを取り込む

生合成

• コレステロールは酢酸を原料として合成される。

acetyl-CoA→hydroxymethyl-glutaryl coenzyme A(HMG-CoA)－(HMG-CoA reductase)→mebaronate→･･･→コレステロール

→コレステロールの生合成

体内循環

• 肝臓は血液循環にVLDLを放出する

血液循環中のVLDLの脂質は、、血管内皮に存在するリポ蛋白リパーゼ(LPL)により分解されて脂肪酸を遊離し、コレステロールの比が高いIDL、LDLとなる。

組織からはコレステロール比型が高いHDLが放出され、そのまま肝臓に取り込まれるか、IDLにコレステロールを渡すことでコレステロールの逆輸送を行っている(内因性の抗動脈硬化作用)。

• 肝臓は血液循環からHDL, IDL, VDLを受容体を介して取り込む

排泄

• 肝臓でコレステロールは胆汁酸に変換され、胆汁として排出される

see HBC.236

Lipoprotein	Source	Diameter (nm)	Density (g/mL)	Composition		Main Lipid Components	Apolipoproteins
				Protein	Lipid
				(%)	(%)
Chylomicrons	Intestine	90～100	< 0.95	1～2	98.99	Triacylglycerol	A-I, A-II, A-IV,1 B-48, C-I, C-II, C-III, E
Chylomicron remnants	Chylomicrons	45～150	< 1.006	6～8	92.94	Triacylglycerol, phospholipids, cholesterol	B-48, E
VLDL	Liver (intestine)	30～90	0.95～1.006	7～10	90～93	Triacylglycerol	B-100, C-I, C-II, C-III
IDL	VLDL	25～35	1.006～1.019	11	89	Triacylglycerol, cholesterol	B-100, E
LDL	VLDL	20～25	1.019～1.063	21	79	Cholesterol	B-100
HDL1	Liver, intestine, VLDL, chylomicrons	20～25	1.019.1.063	32	68	Phospholipids, cholesterol	A-I, A-II, A-IV, C-I, C-II, C-III, D,2 E
HDL2		10～20	1.063～1.125	33	67
HDL3		5～10	1.125～1.210	57	43
Preβ-HDL3		< 5	> 1.210				A-I
Albumin/free fatty	Adipose acids tissue		> 1.281	99	1	Free fatty acids

基準値

• 総コレステロール　：＜220 mg/dl
• HDLコレステロール：≧40 mg/dl
• LDLコレステロール：＜140 mg/dl

脂質異常症→　血清：Total-CHO≧220 mg/dl。LDL-C≧140 mg/dl。TG≧150 mg/dl。HDL-C＜40 mg/dl

参考

• 1.

http://rockymuku.sakura.ne.jp/naibunnpitunaika/koresutero-runotanninokannzann.pdf

「解糖系」

　　[★]

英

glycolytic pathway

同

エムデン-マイヤーホフ経路 Embden-Meyerhof pathway

関

解糖、TCA回路

• CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2OH)H-O- グルコース (OHが↓↓↑↓↑)
• CH(OH)-CH(OH)-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- グルコース-6-リン酸 (OHが↓↓↑↓↑)
• C(CH2OH)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-6-リン酸
• C(CH2O-PO3)OH-C(OH)H-CH(OH)-C(CH2O-PO3)H-O- フルクトース-1,6-リン酸

glucose
↓-hexokinase/glucokinase(liver)
glucose 6-phosphate
↓-phosphohexose isomerase
fructose 6-phosphate
↓-phosphofructokinase
fructose 1,6-bisphosphate
↓-aldolase
glyceraldehyde 3-phosphate
↓-glyceraldehyde-3-phosphate dehydrogenase
1,3-bisphosphoglycerate
↓-phosphoglycerate kinase →ATP
3-phosphoglycerate
↓-phosphoglyceate mutase
2-phosphoglycerate
↓-enolase
phosphoenolpyruvate
↓-pyruvate kinase → ATP
pyruvate
　－(pyruvate dehydrogenase)→acetyl-CoA
　－(pyruvate carboxylase)→oxaloacetate－(NADH+H+)→malate

---

解糖系の酵素 (first aid step1 2006 p.87, FASTEP1_87_酵素一覧.xls)

1	galactokinase	キナーゼ
2	galactose-1-phosphate uridyltransferase	転移酵素
3	hexokinase/glucokinase	キナーゼ
4	glucose-6-phosphatase	ホスファターゼ
5	glucose-6-phosphate dehydrogenase	脱水素酵素
6	transketolase
7	phosphofructokinase	キナーゼ
8	fructose-1,6-bisphosphatase	ホスファターゼ
9	fructokinase	キナーゼ	フルクトキナーゼ
10	aldolase B		アルドラーゼ
11	pyruvate kinase	キナーゼ	ピルビン酸キナーゼ
12	pyruvate dehydrogenase	脱水素酵素	ピルビン酸デヒドロゲナーゼ
13	HMG-CoA reductase	還元酵素	HMG-CoA還元酵素
14	pyruvate carboxylase	カルボキシラーゼ	ピルビン酸カルボキシラーゼ
15	PEP carboxykinase	キナーゼ	PEPカルボキシキナーゼ
16	citrate synthase	合成酵素	クエン酸合成酵素
17	α-ketoglutarate dehydrogenase	脱水素酵素	α-ケトグルタミン酸脱水素酵素
18	ornithine transcarbamylase	転移酵素	オルニチンカルバモイルトランスフェラーゼ

「ビオチン」

　　[★]

英

biotin

同

ビタミンB₇ vitamin B₇、補酵素R coenzyme R、ビタミンH vitamin H

関

ビタミン

機能

• カルボキシラーゼの補酵素となり、CO₂キャリアーとして機能
• 体内で代謝されてビオチン酵素となり、炭素固定反応の補酵素となる。

1. pyruvate －(ピルビン酸カルボキシラーゼ)→ oxaloacetate

2. acetyl-CoA －(アセチルCoAカルボキシラーゼ)→ malonyl-CoA

3. proprionyl-CoA －(プロピオニルCoAカルボキシラーゼ)→ methylmalonyl-CoA　：奇数炭素脂肪酸の偶数炭素脂肪酸への変換、2-オキソ酪酸の代謝

臨床関連

ビオチン欠乏

• dermatitis, enteritis. Caused by antibiotic use, ingestion of raw eggs. (FIRST AID step1 p.114)
• アビジンと強固に結合する。卵白の過剰摂取によりビオチンの吸収が妨げられ欠乏症を生じうる。

「コレステロール生合成」

　　[★]

英

cholesterol biosynthesis, biosynthesis of cholesterol

関

コレステロール

• コレステロールは酢酸を原料として合成される。

acetyl-CoA→hydroxymethyl-glutaryl coenzyme A(HMG-CoA)－(HMG-CoA reductase)→mebaronate→･･･→コレステロール

「アセチル補酵素A」

　　[★]

英

acetyl-coenzyme A, acetyl coenzyme A、acetyl-CoA, acetyl CoA

同

アセチルCoA、アセチルコエンザイムA、アセチル-CoA、アセチル-補酵素A

関

補酵素A

「acetyl-CoA acyltransferase」

　　[★]

アセチルCoAアシルトランスフェラーゼ、アセチルCoAアシル基転移酵素、アセチルCoAアシル転移酵素

関

acetyl-CoA C-acyltransferase、beta-ketothiolase

「acetyl-CoA hydrolase」

　　[★]

アセチルCoA加水分解酵素、アセチルCoAヒドロラーゼ

「acetoacetyl-CoA thiolase deficiency」

　　[★] アセトアセチルCoAチオラーゼ欠損症

「C」

　　[★]

• 炭素 carbon
• シトシン cytosine
• システイン cysteine
• シチジン
• セルシウス度 摂氏 degrees Celsius degree C
• 産婦人科領域で「子宮外頚 子宮外頚部 exocervix」を表現するための略語

　 　 　 　

「CoA」

　　[★]

• 大動脈縮窄症 coactation of the aorta
• 補酵素A coenzyme A

「COA」

　　[★] 補酵素A coenzyme A CoA

「acetyl」

　　[★]

アセチル

関

Ac

　

「Co」

　　[★] コバルト cobalt