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Glycoursodeoxycholic acid

CAT: 0804-HY-N1424-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1424-01Size:5 mg
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Description
Glycoursodeoxycholic acid, a acyl glycine and a bile acid-glycine conjugate, is a metabolite of ursodeoxycholic acid.
CAS Number
64480-66-6
Product Name Alternative
GUDCA; Ursodeoxycholylglycine
UNSPSC
12352211
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/Glycoursodeoxycholic-acid.html
Purity
99.80
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(O)CNC(CC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
Molecular Formula
C26H43NO5
Molecular Weight
449.62
Precautions
H302, H315, H319, H335
References & Citations
[1]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.|[2]Vaz AR, et al. Glycoursodeoxycholic acid reduces matrix metalloproteinase-9 and caspase-9 activation in a cellular model of superoxide dismutase-1 neurodegeneration.|[3]Palmela I, et al. Hydrophilic bile acids protect human blood-brain barrier endothelial cells from disruption by unconjugated bilirubin: an in vitro study. Front Neurosci. 2015 Mar 13;9:80.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite; Microbial Metabolite

Chemical Information

Glycoursodeoxycholic acid

Glycoursodeoxycholic acid is a bile acid glycine conjugate derived from ursoodeoxycholic acid. It has a role as a neuroprotective agent and a human blood serum metabolite. It is a N-acylglycine and a bile acid glycine conjugate. It is functionally related to an ursodeoxycholic acid. It is a conjugate acid of a glycoursodeoxycholate.

CAS Number64480-66-6
PubChem CID12310288
IUPAC Name2-[[(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
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(CC[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
InChI
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
InChIKey
GHCZAUBVMUEKKP-XROMFQGDSA-N
Chemical Structure
2D Structure
2D structure of Glycoursodeoxycholic acid
CAS: 64480-66-6
CID: 12310288
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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