基本情報
- CAS
475-31-0- 標準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- 分子式
- C26H43NO6
- 平均分子量
- 465.6 g/mol
- 単同位体質量
- 465.30903809
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- N-(3α,7α,12α-トリヒドロキシ-24-オキソ-5β-コラン-24-イル)グリシン
- 英語名
- Glycocholic acid
- 分子式
- C26H43NO6
- 分子量
- 465.63
名称と別名
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)-
名称をさらに表示
コリルグリシナートコリルグリシンN-(3α,7α,12α-トリヒドロキシ-24-オキソ-5β-コラン-24-イル)グリシンN-カルボキシメチル-3α,7α,12α-トリヒドロキシ-5β-コラン-24-アミドグリココール酸2-[(3α,7α,12α-トリヒドロキシ-24-オキソ-5β-コラン-24-イル)アミノ]酢酸N-コロイルグリシン2-[(4R)-4-[(1R,3aS,3bR,4R,5aS,7R,9aS,9bS,11S,11aR)-4,7,11-トリヒドロキシ-9a,11a-ジメチル-ヘキサデカヒドロ-1H-シクロペンタ[a]フェナントレン-1-イル]ペンタンアミド]酢酸(3α,7α,12α-トリヒドロキシ-24-オキソ-5β-コラン-24-イル)-Gly-OH
物性
構造計算による物性
- XLogP
- 2.9
- 極性表面積
- 127 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 6
- 回転可能結合数
- 6
- 重原子数
- 33
- 形式電荷
- 0
- 複雑度
- 759
実験および物理化学的性質
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]
202.2 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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%)
安全データ
- wgk
- 3
- ridadr
- UN 3077 9/PG 3
- risk_code
- 51/53
- hazard_code
- N
- safety_code
- 61
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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
用途と製造
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]
応用分野
解説グリセロリン酸3種類の異性体が考えられるが，リン脂質や中性脂肪の骨格をなすのはL-グリセリン3-リン酸で，加水分解中にリン酸基の転位により，一部2-リン酸になる．シロップ状の物質．水，メタノール，エタノールに易溶．グリセリンの水酸基1個とリン酸とがエステル様に結合してできたもので，リン酸基の位置によってα体とβ体とがある。グリセリン発酵の際，グリセロリン酸脱水素酵素によって，ジオキシアセトンリン酸から可逆的に生成される。
説明Glycocholic 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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