cholate

コール酸、(化合物)ール酸塩

関

cholic acid

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/16 21:26:57」(JST)

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Cholic acid

Names
IUPAC name (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
Other names 3α,7α,12α-Trihydroxy-5β-cholanoic acid
Identifiers
CAS Registry Number	81-25-4 Y
ATC code	A05AA03
ChEBI	CHEBI:16359 N
ChEMBL	ChEMBL205596 N
ChemSpider	192176 Y
DrugBank	DB02659 N
InChI InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 Y Key: BHQCQFFYRZLCQQ-OELDTZBJSA-N Y InChI=1/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1 Key: BHQCQFFYRZLCQQ-OELDTZBJBZ
Jmol-3D images	Image
PubChem	221493
SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
UNII	G1JO7801AE Y
Properties
Chemical formula	C24H40O5
Molar mass	408.57 g/mol
Melting point	200 to 201 °C (392 to 394 °F; 473 to 474 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is: Y/N?)
Infobox references

Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of the two major bile acids produced by the liver, where it is synthesized from cholesterol. These two major bile acids are roughly equal in concentration in humans. Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid, respectively.

Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Other species may synthesize different bile acids as their predominant primary bile acids.

Cholic acid, formulated as Cholbam capsules, is approved by the United States Food and Drug Administration as a treatment for children and adults with bile acid synthesis disorders due to single enzyme defects, and for peroxisomal disorders (such as Zellweger syndrome).

Structure of cholic acid showing relationship to other bile acids

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

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|{{{bSize}}}px|alt=Statin Pathway edit]]

File:StatinPathway_WP430.png

Statin Pathway edit

References

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 薬物性肝障害 drug induced liver injury

English Journal

• Assessment of the functionality and stability of detergent purified nAChR from Torpedo using lipidic matrixes and macroscopic electrophysiology.

• Padilla-Morales LF1, Colón-Sáez JO2, González-Nieves JE3, Quesada-González O4, Lasalde-Dominicci JA5.
• Biochimica et biophysica acta.Biochim Biophys Acta.2016 Jan;1858(1):47-56. doi: 10.1016/j.bbamem.2015.10.002. Epub 2015 Oct 8.
• In our previous study we examined the functionality and stability of nicotinic acetylcholine receptor (nAChR)-detergent complexes (nAChR-DCs) from affinity-purified Torpedo californica (Tc) using fluorescence recovery after photobleaching (FRAP) in Lipidic Cubic Phase (LCP) and planar lipid bilayer
• PMID 26454038

• Chirality-dependent densities of carbon nanotubes by in situ 2D fluorescence-excitation and Raman characterisation in a density gradient after ultracentrifugation.

• Cambré S1, Muyshondt P, Federicci R, Wenseleers W.
• Nanoscale.Nanoscale.2015 Dec 21;7(47):20015-24. doi: 10.1039/c5nr06020f. Epub 2015 Nov 13.
• Density gradient ultracentrifugation (DGU) becomes increasingly important for the sorting of nanomaterials according to the particles' density, hence structure and dimensions, which determine their unique properties, but the further development of this separation technique is hindered by the limited
• PMID 26565985

• Assessment of alkaline cholesterol oxidase purified from Rhodococcus sp. PKPD-CL for its halo tolerance, detergent and organic solvent stability.

• Kasabe PJ1, Mali GT1, Dandge PB2.
• Protein expression and purification.Protein Expr Purif.2015 Dec;116:30-41. doi: 10.1016/j.pep.2015.08.011. Epub 2015 Aug 11.
• The novel bacterium, Rhodococcus sp. PKPD-CL was isolated and identified from the 'Chilika Lake' located at Odisha state of India, which is a largest brackish water habitat in Asia. Rhodococcus sp. PKPD-CL produces extracellular halo tolerant, detergent and organic solvent stable alkaline cholestero
• PMID 26276474

Japanese Journal

• Eicosapentaenoic acid attenuates hepatic accumulation of cholesterol esters but aggravates liver injury and inflammation in mice fed a cholate-supplemented high-fat diet

• WATANABE Shiro,TSUNEYAMA Koichi
• Journal of toxicological sciences 38(3), 379-390, 2013-06-01
• NAID 10031158904

• Eicosapentaenoic acid attenuates hepatic accumulation of cholesterol esters but aggravates liver injury and inflammation in mice fed a cholate-supplemented high-fat diet

• Watanabe Shiro,Tsuneyama Koichi
• The Journal of toxicological sciences : an official journal of the Japanese Society of Toxicology 38(3), 379-390, 2013-06
• NAID 40019756710

• Eicosapentaenoic acid attenuates hepatic accumulation of cholesterol esters but aggravates liver injury and inflammation in mice fed a cholate-supplemented high-fat diet

• Watanabe Shiro,Tsuneyama Koichi
• The Journal of Toxicological Sciences 38(3), 379-390, 2013
• … The administration of a sodium cholate-supplemented high-fat (CAHF) diet in mice induced the predominant accumulation of cholesterol esters (CE) in the liver and biochemical and histological features of liver injury. …
• NAID 130004447055

Related Links

• 日本チョコレート・ココア協会

用語辞典やできるまで、シンポジウム情報、チョコレート規約などチョコレート・ココアに関する情報を提供する日本チョコレート・ココア協会のオフィシャルサイトです。 ... [15.09.18] 第20回チョコレート・ココア国際栄養 ...

• CHOCOLATE-CHOCOLATE

CHOCOLATE-CHOCOLATEのHPです。 ... 東日本大震災により、亡くなられた方々のご冥福をお祈り申し上げるとともに、 被災された皆さま、ご家族、ならびにご関係者の皆さまに、心からお見舞いを申し上げます。

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★リンクテーブル★

リンク元	「コール酸塩」
拡張検索	「sodium taurocholate」「taurochenodeoxycholate」「deoxycholate-hydrogen sulfide-lactose agar」「taurodeoxycholate」

「コール酸塩」

　　[★]

英

cholate

関

コール酸

「sodium taurocholate」

　　[★]

• タウロコール酸ナトリウム

関

taurocholate、taurocholic acid

「taurochenodeoxycholate」

　　[★]

タウロケノデオキシコール酸

関

taurochenodeoxycholic acid

「deoxycholate-hydrogen sulfide-lactose agar」

　　[★] DHL寒天。デオキシコール酸塩・硫化水素・乳糖寒天

「taurodeoxycholate」

　　[★]

タウロデオキシコール酸

関

taurodeoxycholic acid