Glycoursodeoxycholic Acid - Moligand™, ≥96% , CAS No.64480-66-6

CAS: 64480-66-6 Cat. No.: G135873 Peso molecular: 449.62

GRADE & PURITY Moligand™, ≥96%

Synonyms

GUDCA | AKOS027250703 | Glycoursodeoxycholic acid | UNII-PF1G5J2X2A | Glycylursodeoxycholic acid | N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine | URSODEOXYCHOLYLGLYCINE, (+)- | AS-58487 | s6146 | Ursodeoxycholylglycine | LMST05030016 | AKOS04076

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Sinónimos

GUDCA | AKOS027250703 | Glycoursodeoxycholic acid | UNII-PF1G5J2X2A | Glycylursodeoxycholic acid | N-[(3a, 5b, 7b)-3, 7-Dihydroxy-24-oxocholan-24-yl]glycine | URSODEOXYCHOLYLGLYCINE, (+)- | AS-58487 | s6146 | Ursodeoxycholylglycine | LMST05030016 | AKOS04076

Especificaciones y pureza

Moligand™, ≥96%

Mecanismos bioquímicos y fisiológicos

Secondary bile acids derived from acylglycines. Glycideoxycholic acid (GUDCA) has been reported to have cytoprotective and anti-inflammatory effects.

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥96%

Nombres e identificadores

• Pubchem Sid: 504767054
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504767054
• Sonrisas canónicas: CC(CCC(=O)NCC(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• IUPAC Name: 2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-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
• InChIKey: GHCZAUBVMUEKKP-XROMFQGDSA-N
• INCHI: 1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
• Isómeros SMILES: C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• WGK Alemania: 3
• Peso molecular: 449.62
• Reaxy-Rn: 28775435
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=28775435&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Steroids and steroid derivatives
• Subclass: Bile acids, alcohols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Glycinated bile acids and derivatives
• Alternative Parents: Dihydroxy bile acids, alcohols and derivatives 7-alpha-hydroxysteroids 3-alpha-hydroxysteroids N-acyl-alpha amino acids N-acyl amines Secondary carboxylic acid amides Secondary alcohols Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Glycinated bile acid - Dihydroxy bile acid, alcohol, or derivatives - Hydroxy bile acid, alcohol, or derivatives - 3-hydroxysteroid - Hydroxysteroid - 7-hydroxysteroid - 7-alpha-hydroxysteroid - 3-alpha-hydroxysteroid - N-acyl-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Fatty amide - Fatty acyl - N-acyl-amine - Cyclic alcohol - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Carboxylic acid - Organooxygen compound - Organopnictogen compound - Organic nitrogen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic oxygen compound - Organonitrogen compound - Aliphatic homopolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as glycinated bile acids and derivatives. These are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
• External Descriptors: C24 bile acids, alcohols, and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC10A2 Tclin Ileal bile acid transporter (415 Activities)

Discover Target: SLC10A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)

Discover Target: GPBAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nr1h4 Bile acid receptor (142 Activities)

Discover Target: Nr1h4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)

Discover Target: Slco1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc10a2 Ileal sodium/bile acid cotransporter (17 Activities)

Discover Target: Slc10a2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a5 Solute carrier organic anion transporter family member 1A5 (48 Activities)

Discover Target: Slco1a5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: heat sensitive
• Punto de fusión (°C): 233 °C
• Peso molecular: 449.600 g/mol
• XLogP3: 4.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 449.314 Da
• Monoisotopic Mass: 449.314 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 727.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Wei Xu, Yingying Kong, Tuo Zhang, Zhihua Gong, Wenjun Xiao.  (2022)  L-Theanine regulates lipid metabolism by modulating gut microbiota and bile acid metabolism.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  103  (3): (1283-1293).  [PMID:36087337] [10.1002/jsfa.12222]

2. Cui Xiping, He Qiyi, Yang Huiyi, Chen Yingshan, Shen Ding, Eremin Sergei A., Mu Yunping, Zhao Suqing.  (2021)  Development of enzyme-free single-step immunoassays for glycocholic acid based on palladium nanoparticle-mediated signal generation.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  413  (23): (5733-5742).  [PMID:34476526] [10.1007/s00216-021-03548-5]

3. Qiyi He, Yanxiong Fang, Huiyi Yang, Ding Shen, Yingshan Chen, Yingying Zhong, Xiangguang Li, Sergei A. Eremin, Xiping Cui, Suqing Zhao.  (2021)  Enhanced performance of a surface plasmon resonance-based immunosensor for the detection of glycocholic acid.  Analytical Methods,  13  (16): (1919-1924).  [PMID:33913980] [10.1039/D1AY00357G]

4. Shun Zhang, Ting Cai, Jing Lin, Jia-Juan Liu, Yong-Gang Zhao, Min-Yi Cao.  (2024)  Analysis of 15 bile acids in human plasma based on C18 functionalized magnetic organic polymer nanocomposite coupled with liquid chromatography-tandem mass spectrometry.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38704923] [10.1016/j.chroma.2024.464962]

5. Ruijiao Zhu, Liuxin Li, Meimei Zhao, Boya Zhang, Ziyi Zhang, Mengcong Li, Lu Yu, Ziwei Song, Ning Gu.  (2026)  Polysaccharide from Ribes nigrum L. Ameliorates Diabetic Kidney Injury in Mice by Modulating the GUDCA/GPBAR1 Axis through the Remodeling of the Gut Microbiota.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:] [10.1021/acs.jafc.5c16173]