Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H43NO6 |
Molecular Weight | 465.6227 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCC(O)=O
InChI
InChIKey=RFDAIACWWDREDC-FRVQLJSFSA-N
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
Molecular Formula | C26H43NO6 |
Molecular Weight | 465.6227 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/28942640
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28942640
Glycocholic acid (GCA) is an important metabolite of bile acids, a conjugate of cholic acid with glycine. GCA urine levels are expected to be a specific diagnostic biomarker for hepatocellular carcinoma (HCC). The average GCA concentrations of HCC patients in plasma and urine were about 25 and 2.8 times than that of healthy volunteers.
Approval Year
PubMed
Title | Date | PubMed |
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Ocular tolerance of absorption enhancers in ophthalmic preparations. | 2002 |
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Carriers involved in targeting the cytostatic bile acid-cisplatin derivatives cis-diammine-chloro-cholylglycinate-platinum(II) and cis-diammine-bisursodeoxycholate-platinum(II) toward liver cells. | 2002 Apr |
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Bile salt aggregates in the gas phase: an electrospray ionization mass spectrometric study. | 2002 Apr 15 |
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Examination of the solubilization of drugs by bile salt micelles. | 2002 Aug |
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Maldigestion and malabsorption of dietary lipid during severe childhood malnutrition. | 2002 Dec |
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[Observation on effect of danxiaoling in supplementary treatment of intrahepatic cholestasis in pregnancy]. | 2002 Feb |
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Nasal glucagon delivery using microcrystalline cellulose in healthy volunteers. | 2002 Feb 21 |
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Buccal transport of flecainide and sotalol: effect of a bile salt and ionization state. | 2002 Jul 8 |
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Colesevelam hydrochloride. | 2002 May 15 |
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Ion conductors derived from biogenic amines, bile acids, and amino acids. | 2002 Nov-Dec |
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[Maternal-fetal mixed lymphocyte culture in intrahepatic cholestasis of pregnancy]. | 2002 Sep |
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[Relationship between human leukocyte antigen-DRB1 allele gene polymorphism and intrahepatic cholestasis of pregnancy]. | 2002 Sep |
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A monoclonal antibody-based enzyme-linked immunosorbent assay of glycolithocholic acid sulfate in human urine for liver function test. | 2002 Sep |
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[Comparative characteristics of lipid components of gallbladder and liver bile fractions in children with chronic cholecystitis]. | 2003 |
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Sensitivity of bile acid transport by organic anion-transporting polypeptides to intracellular pH. | 2003 Apr 1 |
|
Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. | 2003 Aug |
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Determination of ursodeoxycholic acid in pharmaceutical preparations by capillary electrophoresis with indirect UV detection. | 2003 Aug 8 |
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Substitution of Trp1242 of TM17 alters substrate specificity of human multidrug resistance protein 3. | 2003 Feb |
|
Sodium glycocholate transport across Caco-2 cell monolayers, and the enhancement of mannitol transport relative to transepithelial electrical resistance. | 2003 Feb 18 |
|
Influence of emulsifiers on the crystallization of solid lipid nanoparticles. | 2003 Jul |
|
Quantification of bile acids directly from urine by MALDI-TOF-MS. | 2003 Mar |
|
Differential effects of metformin on bile salt absorption from the jejunum and ileum. | 2003 Mar |
|
Oral bile acids reduce bacterial overgrowth, bacterial translocation, and endotoxemia in cirrhotic rats. | 2003 Mar |
|
Effect of ursodeoxycholic acid on the impairment induced by maternal cholestasis in the rat placenta-maternal liver tandem excretory pathway. | 2003 May |
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Potential utility of various protease inhibitors for improving the intestinal absorption of insulin in rats. | 2003 Nov |
|
Steroid ring hydroxylation patterns govern cooperativity in human bile acid binding protein. | 2003 Oct 14 |
|
Metabolism and absorption enhancement of methionine enkephalin in human nasal epithelium. | 2004 Apr |
|
[Analysis on therapeutic effect of Western and Chinese drug in treating intrahepatic cholestasis pregnancy]. | 2004 Apr |
|
Cytotoxicity evaluation of enzyme inhibitors and absorption enhancers in Caco-2 cells for oral delivery of salmon calcitonin. | 2004 Apr |
|
Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids. | 2004 Aug 6 |
|
[Effects of protease inhibitors on intestinal absorption of insulin]. | 2004 Feb |
|
Transcriptional regulation of human mucin MUC4 by bile acids in oesophageal cancer cells is promoter-dependent and involves activation of the phosphatidylinositol 3-kinase signalling pathway. | 2004 Feb 1 |
|
Alkanoylsucroses in nasal delivery of low molecular weight heparins: in-vivo absorption and reversibility studies in rats. | 2004 Jan |
|
Poly(N,N,N-trimethylammoniumalkyl acrylamide chloride) based hydrogels for serum cholesterol reduction. | 2004 Jan-Feb |
|
Acid and bile salts induce DNA damage in human oesophageal cell lines. | 2004 Jul |
|
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging. | 2004 Jul 1 |
|
Quantification of bile acids directly from plasma by MALDI-TOF-MS. | 2004 Mar |
|
Sensitization of mechanosensitive gastric vagal afferent fibers in the rat by thermal and chemical stimuli and gastric ulcers. | 2004 May |
|
Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. | 2004 Oct 1 |
|
High-speed digital imaging method for ciliary beat frequency measurement. | 2005 Apr |
|
Two common PFIC2 mutations are associated with the impaired membrane trafficking of BSEP/ABCB11. | 2005 Apr |
|
Improvement of absorption enhancing effects of n-dodecyl-beta-D-maltopyranoside by its colon-specific delivery using chitosan capsules. | 2005 Apr 11 |
|
[Cholyl glycine (CG)]. | 2005 Aug |
|
Ileal bile acid-binding protein, functionally associated with the farnesoid X receptor or the ileal bile acid transporter, regulates bile acid activity in the small intestine. | 2005 Dec 23 |
|
Vectorial transport of bile salts across MDCK cells expressing both rat Na+-taurocholate cotransporting polypeptide and rat bile salt export pump. | 2005 Jan |
|
The influence of the ionic medium on the behaviour of sodium glycocholate and cholate aqueous solutions. | 2005 Jan-Feb |
|
Stable ciliary activity in human nasal epithelial cells grown in a perfusion system. | 2005 Mar 23 |
|
mu-Opiate receptor agonist loperamide blocks bethanechol-induced gallbladder contraction, despite higher cholecystokinin plasma levels in man. | 2005 Oct |
|
Diastereomeric molecular recognition and binding behavior of bile acids by L/D-tryptophan-modified beta-cyclodextrins. | 2005 Oct 28 |
|
Saturated phospholipids promote crystallization but slow down polymorphic transitions in triglyceride nanoparticles. | 2005 Oct 3 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:48:37 UTC 2023
by
admin
on
Wed Jul 05 22:48:37 UTC 2023
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Record UNII |
G59NX3I3RT
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English | ||
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Common Name | English |
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NCI_THESAURUS |
C843
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LOINC |
2100-6
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CFR |
21 CFR 862.1177
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G59NX3I3RT
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10140
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SUB22781
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C77849
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17687
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DTXSID2047436
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1426482
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DB02691
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D006000
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100000088797
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GLYCOCHOLIC ACID
Created by
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G59NX3I3RT
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475-31-0
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207-494-9
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M5799
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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LABELED -> NON-LABELED |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |