기본 정보
- CAS
475-31-0- 표준 SMILES
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C- InChIKey
RFDAIACWWDREDC-FRVQLJSFSA-N- 분자식
- C26H43NO6
- 평균 분자량
- 465.6 g/mol
- 단동위원소 질량
- 465.30903809
개요
Glycocholic acid is a bile acid glycine conjugate having cholic acid as the bile acid component. It has a role as a human metabolite. It is functionally related to a cholic acid and a glycochenodeoxycholic acid. It is a conjugate acid of a glycocholate.
이름 및 식별자
- 우선 이름
- Glycocholic Acid
- IUPAC
- 2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
- 영어명
- Glycocholic acid
- 분자식
- C26H43NO6
- 분자량
- 465.63
이름 및 동의어
Glycocholic acid475-31-0CholylglycineN-CholoylglycineDTXSID2047436G59NX3I3RT2-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acidDTXCID0027436CHEBI:17687N-(3Alpha,7Alpha,12Alpha-trihydroxy-5Beta-cholan-24-oyl)-glycineN-((3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl)glycineGlycine, N-((3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl)-
이름 더 보기
GLYCITINGLYCOCHOLIC ACID HYDRATEN-CholylglycineCholylglycinate[(3,7,12-Trihydroxy-24-oxocholan-24-yl)amino]acetic acidGLYCOCHOLICN-cholyglycineglycocholicaci
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid2-(((4R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoyl)amino)acetic acid2-((4R)-4-((1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadecan-14-yl)pentanamido)acetic acidRefChem:389020Glycine, N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24-oxocholan-24-yl]-207-494-9glycocholate
물성
구조 계산 물성
- XLogP
- 2.9
- 극성 표면적
- 127 Ų
- 수소 결합 공여자 수
- 5
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 33
- 형식 전하
- 0
- 복잡도
- 759
실험 및 물리화학적 성질
Chemical Classes
Bile Acids -> Quant Bile Acids
Biological Agents -> Other Biomolecules
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Sterol Lipids [ST] -> Steroid conjugates [ST05] -> Glycine conjugates [ST0503]
LogP
1.65
1.65
Food AdditivesPH CONTROL AGENT -> FDA Substance added to food
Solubility0.0033 mg/mL
Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point170 °C
Physical Description
Dihydrate: Solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
201.7 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2047436]
196.9 Ų [M+H-2H2O]+ [CCS Type: DT; Method: single field calibrated]
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
유해성 정보
Regulatory InformationGlycocholic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
안전 데이터
- wgk
- 3
- ridadr
- UN 3077 9/PG 3
- risk_code
- 51/53
- hazard_code
- N
- safety_code
- 61
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
MeSH Pharmacological Classification
Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.
Tissue LocationsFibroblasts
Cellular LocationsExtracellular
Metabolite Pathways27-Hydroxylase Deficiency
용도 및 제조
UsesMain constituent of the bile of herbivorous animals; [Merck Index] Functions as a detergent to solubilize fats for absorption and is absorbed itself; [ChemIDplus] Used as a Ph control agent for foods; [FDA]
응용 분야
개요Glycocholic acid is a glycine-conjugated form of the primary bile acid cholic acid and has roles in the emulsification of fats. It reduces expression of the gene encoding the farnesoid X receptor (FXR) and increases expression of the genes encoding the bile acid receptors TGR5 and S1PR2 in SNU-245 cells when used at a concentration of 1.6 μmol/ml. Glycocholic acid (250 μM) increases the intracellular accumulation and cytotoxicity of epirubicin in Caco-2 cells, as well as decreases expression of the genes encoding multidrug resistance protein 1 (MDR1), MDR-associated protein 1 (MRP1), and MRP2 when used alone or in combination with epirubicin. It increases absorption of epirubicin into everted sacs of rat ileum and jejunum when used at a concentration of 250 μM. The bile acid composition ratio of glycocholic acid is elevated in bile of patients with cholangiocarcinoma compared with patients with pancreatic cancer or benign biliary diseases. Serum levels of glycocholic acid are elevated in patients with hepatocellular carcinoma compared with healthy individuals.
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