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Glycodeoxycholic acid

CAT: 0804-HY-125731-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-125731-01Size:100 mg
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Description
Glycodeoxycholic Acid is a natural product found in Streptomyces nigricans, Trypanosoma brucei and C. elegans. Glycodeoxycholic Acid induces hepatocyte necrosis and autophagy in patients with obstructive cholestasis[1][2][3].
CAS Number
360-65-6
UNSPSC
12352211
Hazard Statement
H315, H319, H335
Target
Autophagy; Endogenous Metabolite; STAT
Type
Natural Products
Related Pathways
Autophagy; JAK/STAT Signaling; Metabolic Enzyme/Protease; Stem Cell/Wnt
Applications
Neuroscience-Neuromodulation
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/glycodeoxycholic-acid.html
Concentration
10mM
Purity
99.91
Solubility
DMSO : 87.5 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
C[C@@H]([C@]1(CC[C@]2([C@@]3(CC[C@@]4(C[C@@H](CC[C@@]4([C@]3(C[C@@H]([C@@]21C)O)[H])C)O)[H])[H])[H])[H])CCC(NCC(O)=O)=O
Molecular Formula
C26H43NO5
Molecular Weight
449.62
Precautions
H315, H319, H335
References & Citations
[1]Shi C, et al. Glycochenodeoxycholic acid induces stemness and chemoresistance via the STAT3 signaling pathway in hepatocellular carcinoma cells. Aging (Albany NY) . 2020 Aug 3;12 (15) :15546-15555.|[2]Vaz AR, et al. Bilirubin selectively inhibits cytochrome c oxidase activity and induces apoptosis in immature cortical neurons: assessment of the protective effects of glycoursodeoxycholic acid. J Neurochem. 2010 Jan;112 (1) :56-65.|[3]Fauzi A, et al. Role of glycodeoxycholic acid to induce acute pancreatitis in Macaca nemestrina. J Med Primatol. 2022 Jun;51 (3) :134-142. doi: 10.1111/jmp.12577. Epub 2022 Mar 20. PMID: 35306662; PMCID: PMC9310849.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Glycodeoxycholic Acid

Glycodeoxycholic acid is a bile acid glycine conjugate of deoxycholic acid. It has a role as a human metabolite. It is functionally related to a deoxycholic acid. It is a conjugate acid of a glycodeoxycholate.

CAS Number360-65-6
PubChem CID3035026
IUPAC Name2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-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
Molecular FormulaC26H43NO5
Molecular Weight449.6
XLogP4.3
Topological Polar Surface Area107
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Heavy Atom Count32
Formal Charge0
Complexity727
SMILES
C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI
InChI=1S/C26H43NO5/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-/m1/s1
InChIKey
WVULKSPCQVQLCU-BUXLTGKBSA-N
Chemical Structure
2D Structure
2D structure of Glycodeoxycholic Acid
CAS: 360-65-6
CID: 3035026
Formula: C26H43NO5
MW: 449.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight449.6
XLogP34.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Exact Mass449.31412347
Monoisotopic Mass449.31412347
Topological Polar Surface Area107 Ų
Heavy Atom Count32
Formal Charge0
Complexity727
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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TRC-G641402-10MGGlycodeoxycholic Acid-D5
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