알파-케토아이소카프로산

알파-케토아이소카프로산
α-Ketoisocaproic acid
이름
	IUPAC 이름 4-Methyl-2-oxopentanoic acid
	체계명 4-Methyl-2-oxopentanoic acid
	별칭 4-Methyl-2-oxovaleric acid
식별자
CAS 번호	816-66-0 ;
3D 모델 (JSmol)	Interactive image; Interactive image;
3DMet	B00066;
바일슈타인; 레퍼런스	1701823
ChEBI	CHEBI:48430 ;
ChEMBL	ChEMBL445647 ;
ChemSpider	69 ;
DrugBank	DB03229 ;
ECHA InfoCard	100.011.304
EC 번호	212-435-5;
IUPHAR/BPS	4656;
KEGG	C00233 ;
MeSH	Alpha-ketoisocaproic+acid
PubChem CID	70;
UNII	4GUJ8AH400 ;
UN 번호	3265
CompTox Dashboard (EPA)	DTXSID6061157 ;
	InChI InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) Key: BKAJNAXTPSGJCU-UHFFFAOYSA-N ; InChI=1/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) Key: BKAJNAXTPSGJCU-UHFFFAOYAG;
	SMILES CC(C)CC(=O)C(O)=O; O=C(C(=O)O)CC(C)C;
성질
화학식	C6H10O3
몰 질량	130.143 g·mol−1
밀도	1.055 g cm−3 (at 20 °C)
녹는점	8 to 10 °C (46 to 50 °F; 281 to 283 K)
끓는점	85 °C (185 °F; 358 K) at 13 mmHg
log P	0.133
산성도 (pKa)	2.651
염기도 (pKb)	11.346
위험
EU classification (DSD) (outdated)	C
R-phrases (outdated)	R34
S-phrases (outdated)	S26, S36/37/39, S45
	달리 명시된 경우를 제외하면, 표준상태(25 °C [77 °F], 100 kPa)에서 물질의 정보가 제공됨. 확인 (관련 정보 ?) 정보상자 각주

α-케토아이소카프로산(영어: α-ketoisocaproic acid) 또는 4-메틸-2-옥소펜탄산(영어: 4-methyl-2-oxopentanoic acid)^[2]은 류신의 대사 과정에서의 대사 중간생성물이다.

류신의 대사 경로

사람에서 L-류신과 관련한 β-하이드록시 β-메틸뷰티르산(HMB) 및 아이소발레릴-CoA에 대한 대사 경로. 두 가지 주요 경로 중 L-류신은 대부분 아이소발레릴-CoA로 대사되는 반면, β-하이드록시 β-메틸뷰티르산(HMB)으로 대사되는 경우는 약 5%에 불과하다.^[3]^[4]^[5]

각주

↑ (영어) 알파-케토아이소카프로산 - PubChem
↑ (영어) 알파-케토아이소카프로산 - PubChem
↑ Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). “International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)”. 《Journal of the International Society of Sports Nutrition》 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064. PMID 23374455.
↑ Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). “HMB supplementation: clinical and athletic performance-related effects and mechanisms of action”. 《Amino Acids》 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).
↑ Kohlmeier M (May 2015). 〈Leucine〉. 《Nutrient Metabolism: Structures, Functions, and Genes》 2판. Academic Press. 385–388쪽. ISBN 978-0-12-387784-0. 2016년 6월 6일에 확인함. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
Figure 8.57: Metabolism of L-leucine

[1] (영어) 알파-케토아이소카프로산 - PubChem

[2] (영어) 알파-케토아이소카프로산 - PubChem

[3] Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). “International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)”. 《Journal of the International Society of Sports Nutrition》 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064. PMID 23374455.

[4] Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). “HMB supplementation: clinical and athletic performance-related effects and mechanisms of action”. 《Amino Acids》 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).

[5] Kohlmeier M (May 2015). 〈Leucine〉. 《Nutrient Metabolism: Structures, Functions, and Genes》 2판. Academic Press. 385–388쪽. ISBN 978-0-12-387784-0. 2016년 6월 6일에 확인함. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
Figure 8.57: Metabolism of L-leucine

[1]

[2]

[3]

[4]

[5]

이름

IUPAC 이름 4-Methyl-2-oxopentanoic acid
체계명 4-Methyl-2-oxopentanoic acid^[1]
별칭 4-Methyl-2-oxovaleric acid
식별자
CAS 번호	816-66-0^예
3D 모델 (JSmol)	Interactive image Interactive image
3DMet	B00066
바일슈타인 레퍼런스	1701823
ChEBI	CHEBI:48430^예
ChEMBL	ChEMBL445647^예
ChemSpider	69^예
DrugBank	DB03229^예
ECHA InfoCard	100.011.304
EC 번호	212-435-5
IUPHAR/BPS	4656
KEGG	C00233^예
MeSH	Alpha-ketoisocaproic+acid
PubChem CID	70
UNII	4GUJ8AH400^예
UN 번호	3265
CompTox Dashboard (EPA)	DTXSID6061157
InChI InChI=1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)^예 Key: BKAJNAXTPSGJCU-UHFFFAOYSA-N^예 InChI=1/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9) Key: BKAJNAXTPSGJCU-UHFFFAOYAG
SMILES CC(C)CC(=O)C(O)=O O=C(C(=O)O)CC(C)C
성질
화학식	C₆H₁₀O₃
몰 질량	130.143 g·mol⁻¹
밀도	1.055 g cm⁻³ (at 20 °C)
녹는점	8 to 10 °C (46 to 50 °F; 281 to 283 K)
끓는점	85 °C (185 °F; 358 K) at 13 mmHg
log P	0.133
산성도 (pK_a)	2.651
염기도 (pK_b)	11.346
위험
EU classification (DSD) (outdated)	C
R-phrases (outdated)	R34
S-phrases (outdated)	S26, S36/37/39, S45
달리 명시된 경우를 제외하면, 표준상태(25 °C [77 °F], 100 kPa)에서 물질의 정보가 제공됨. 예 확인 (관련 정보 ^예아니오 ?) 정보상자 각주

알파-케토아이소카프로산

류신의 대사 경로

각주

€4.95