2-Arachidonylglycerol

HCID 5282280CAS 53847-30-6

기본 정보

표준 SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC(CO)CO
InChIKey
RCRCTBLIHCHWDZ-DOFZRALJSA-N
분자식
C23H38O4
평균 분자량
378.5 g/mol
단동위원소 질량
378.2770097

개요

2-arachidonoylglycerol is an endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol. It has a role as a human metabolite. It is a 2-acylglycerol 20:4 and an endocannabinoid. It is functionally related to an arachidonic acid.

이름 및 식별자

우선 이름
2-Arachidonylglycerol
IUPAC
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
영어명
2-AG
분자식
C23H38O4
분자량
378.55

이름 및 동의어

2-arachidonoylglycerol53847-30-62-Arachidonylglycerol2-Arachidonyl-glycerol2-Arachidonoyl-glycerolglyceryl 2-arachidonate2-Ara-Gl2-Monoarachidonoylglycerol8D239QDW645,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (all-Z)-5,8,11,14-Eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5Z,8Z,11Z,14Z)-CHEBI:52392
이름 더 보기
(5Z,8Z,11Z,14Z)-1,3-Dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoateNOLADIN2-Monoarachidonin2-Arachidonyl Glycerol (90%)2-Arachidonyl Glycerol (~70%)
DTXSID0010174541,3-Dihydroxy-2-propanyl (5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoateRefChem:85501DTXCID308902342-AG2-Arachidonoyl Glycerol1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate2-Arachidonyl glycerol

데이터베이스 식별자

CAS
53847-30-6
PubChem CID
5282280
DTXSID
DTXSID001017454
ChEMBL
CHEMBL122972
ChEBI
CHEBI:52392
UNII
8D239QDW64
Nikkaji
J671.147B

물성

구조 계산 물성

XLogP
5.3
극성 표면적
66.8 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
4
회전 가능 결합 수
18
무거운 원자 수
27

실험 및 물리화학적 성질

LipidsLipids -> Glycerolipids [GL] -> Monoradylglycerols [GL01] -> Monoacylglycerols [GL0101]
Physical DescriptionSolid

물리화학적 성질

끓는 점
508.6 · 508.6±50.0 °C(Predicted)
밀도
0.992 · 0.992±0.06 g/cm3(Predicted)
인화점
2 °C · 2 °C
저장 조건
-20 °C · -20°C
용해도
10 mg/ml; · DMSO: 10 mg/ml; Ethanol: Miscible; PBS (pH 7.2): ~150 μg/ml
물리적 상태
아세토니트릴 용액

안전 및 규제

안전 데이터

wgk
2
ridadr
UN 1648 3/PG 2
risk_code
11-20/21/22-36
hazard_code
F,Xn
safety_code
26-36/37-16
스토리지 클래스
12 - Non Combustible Liquids

화학 및 산업

약리 정보

MeSH Pharmacological ClassificationCompounds that interact with and stimulate the activity of CANNABINOID RECEPTORS.
Tissue LocationsAll Tissues
Cellular LocationsExtracellular
응용 분야 · 2건

용도2-Arachidonoylglycerol is a major endocannabinoid, which can inhibit synaptic transmission by presynaptic cannabinoid CB1 receptors. It plays an inhibitory role in the bombesin-induced activation of central adrenomedullary outflow in rats.

일반 설명2-Arachidonoylglycerol (2-AG), is an endocannabinoid, an endogenous agonist of the CB1 receptor. 2-AG, unlike anandamide, is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in mouse and rat brain (~5-10 nmol/g tissue). Detection of 2-AG in brain tissue is complicated by the relative ease of its isomerization to 1-AG during standard lipid extraction conditions. Unlike anandamide, formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C (PLC) and diacylglycerol lipase (DAGL). 2-AG acts as a full agonist at the CB1 receptor. At a concentration of 0.3nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a CB1 receptor-dependent mechanism. 2-AG is hydrolyzed in vitro by monoacylglycerol lipase (MAGL), fatty acid amide hydrolase (FAAH), and the uncharacterized serine hydrolase enzymes ABHD6 and ABHD12.

공급사46 곳

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杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]

추가 설명

정의ChEBI: An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol.

관련 반응

2건

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