acetoacetyl-CoA

HCID 92153CAS 1420-36-6

기본 정보

표준 SMILES: CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O
InChIKey: OJFDKHTZOUZBOS-CITAKDKDSA-N
분자식: C25H40N7O18P3S
평균 분자량: 851.6 g/mol
단동위원소 질량: 851.13633833

개요

Acetoacetyl-CoA is a 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is functionally related to an acetoacetic acid and a butyryl-CoA. It is a conjugate acid of an acetoacetyl-CoA(4-).

이름 및 식별자

우선 이름: acetoacetyl-CoA
IUPAC: S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxobutanethioate
영어명: S-acetoacetylcoenzyme A
분자식: C25H40N7O18P3S
분자량: 851.61

이름 및 동의어

acetoacetyl-CoA1420-36-6Acetoacetyl coenzyme AAcetoacetyl coa3-acetoacetyl-CoAS-Acetoacetyl-CoAS-acetoacetyl-coenzyme ACHEBI:15345S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 3-oxobutanethioateS-(2-(3-(((2R)-4-((((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-2-hydroxy-3,3-dimethylbutanoyl)amino)propanoylamino)ethyl) 3-oxobutanethioateRefChem:552369(((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(((hydroxy(((hydroxy(3-hydroxy-2,2-dimethyl-3-((2-((2-((3-oxobutanoyl)sulfanyl)ethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphoryl)oxy))phosphoryl)oxy)methyl)oxolan-3-yl)oxy)phosphonic acid

이름 더 보기

Acetoacetyl coenzymeA[A1625]Coenzyme A S-(3-oxobutanoate)Coenzyme A Impurity 2 （S-Acetoacetate Coenzyme A)(Acetoacetyl-CoA)5'-O-[[[(5,9-Diaza-3-hydroxy-2,2-dimethyl-4,8,13,15-tetraoxo-12-thiahexadecan)-1-yl]phosphono]phosphono]adenosine-3'-phosphoric acid[5-(6-aminopurin-9-yl)-4-hydroxy-2-[[hydroxy-[hydroxy-[3-hydroxy-2,2-dimethyl-3-[2-[2-(3-oxobutanoylsulfanyl)ethylcarbamoyl]ethylcarbamoyl]propoxy]-phosphoryl]oxy-phosphoryl]oxymethyl]oxolan-3-yl]oxyphosphonic acid

215-815-9S-Acetoacetylcoenzyme Aacetoacetyl-coenzyme aAcetoacetylcoenzyme ACoenzyme A, S-acetoacetateS-(2-(3-((2R)-4-(((((((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-2-hydroxy-3,3-dimethylbutanamido)propanamido)ethyl) 3-oxobutanethioateacetoacetyl-S-CoAS-Acetoacetate Coenzyme A

데이터베이스 식별자

CAS: 1420-36-6
PubChem CID: 92153
DTXSID: DTXSID30931292
ChEBI: CHEBI:15345
EC Number: 215-815-9
Nikkaji: J670.888I

물성

구조 계산 물성

XLogP: -5.8
극성 표면적: 406 Å²
수소 결합 공여자 수: 9
수소 결합 수용자 수: 23
회전 가능 결합 수: 22
무거운 원자 수: 54
형식 전하: 0
복잡도: 1,490

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Fatty acyl CoAs [FA0705]

Physical DescriptionSolid

Collision Cross Section247.8 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

물리화학적 성질

밀도: 1.87 · 1.87±0.1 g/cm3(Predicted)
저장 조건: -20 °C · -20°C
용해도: 메탄올(소량으로 용해, 난방, 초음파 처리), 물
산도 계수 (pKa): 1.16 · 1.16±0.50(Predicted)
물리적 상태: 고체
색상: 흰색에서 황백색까지
생물학적 소스: synthetic (Organic)
수용성: 2 O: · H2O: soluble~-50g/L
InChIKey: OJFDKHTZOUZBOS-CITAKDKDSA-N
SMILES: [Na+].[Na+].[Na+].CC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n2cnc3c(N)ncnc23

안전 및 규제

안전 데이터

wgk: 3
스토리지 클래스: 11 - Combustible Solids

화학 및 산업

약리 정보

Tissue LocationsFibroblasts

Cellular LocationsExtracellular

Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

응용 분야 · 1건

용도Acetoacetyl coenzyme A (Acetoacetyl-CoA) may be used as a substrate for a number of enzymes including; acetoacetyl-CoA thiolase (EC 2.3.1) which produces acetyl-CoA in reverse condensation reaction and (3-Hydroxy-3-methylglutaryl coenzyme A (CoA) synthase (HMGCS)) which produces 3-hydroxy-3-methylglutaryl (HMG)-CoA in the mevalonate pathway leading to terpenoid biosynthesis. Acetoacetyl-CoA is also a precursor of poly-beta-hydroxybutyrate polymers in microorganisms.