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Chenodeoxycholic acid 3-glucuronide

CAT: 0804-HY-W585876-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W585876-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Chenodeoxycholic acid 3-glucuronide is a metabolite of Chenodeoxycholic acid that can activate the key nuclear receptor (FXR), with an EC50 of 8 μM, and in HEK293T cells, the EC50 for activating FXR is 11 μM[1].
CAS Number
58814-71-4
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
FXR
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/chenodeoxycholic-acid-3-glucuronide.html
Purity
99.9
Solubility
DMSO : 2.5 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
C[C@@]12[C@]3([H])[C@]([C@@H](C[C@]1([H])C[C@@H](CC2)O[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)C(O)=O)O)([H])[C@@]5([H])[C@](CC3)([C@@](CC5)([H])[C@H](C)CCC(O)=O)C
Molecular Formula
C30H48O10
Molecular Weight
568.70
Precautions
H302, H315, H319, H335
References & Citations
[1]Serena Mostarda, et al. Synthesis, physicochemical properties, and biological activity of bile acids 3-glucuronides: Novel insights into bile acid signalling and detoxification. Eur J Med Chem. 2018 Jan 20:144:349-358.
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

Chenodeoxycholic acid 3-glucuronide

Chenodeoxycholic acid 3-O-(beta-D-glucuronide) is a steroid glucosiduronic acid that is chenodeoxycholic acid having a single beta-D-glucuronic acid residue attached at position 3. It has a role as a human urinary metabolite. It is a beta-D-glucosiduronic acid, a steroid glucosiduronic acid and a dicarboxylic acid. It is functionally related to a chenodeoxycholic acid. It is a conjugate acid of a chenodeoxycholate 3-O-(beta-D-glucuronide)(2-).

CAS Number58814-71-4
PubChem CID20849182
IUPAC Name(2S,3S,4S,5R,6R)-6-[[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-17-[(2R)-4-carboxybutan-2-yl]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC30H48O10
Molecular Weight568.7
XLogP3.6
Topological Polar Surface Area174
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Heavy Atom Count40
Formal Charge0
Complexity959
SMILES
C[C@H](CCC(=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@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C)O)C
InChI
InChI=1S/C30H48O10/c1-14(4-7-21(32)33)17-5-6-18-22-19(9-11-30(17,18)3)29(2)10-8-16(12-15(29)13-20(22)31)39-28-25(36)23(34)24(35)26(40-28)27(37)38/h14-20,22-26,28,31,34-36H,4-13H2,1-3H3,(H,32,33)(H,37,38)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24+,25-,26+,28-,29+,30-/m1/s1
InChIKey
GDNGOAUIUTXUES-BWGRGVIUSA-N
Chemical Structure
2D Structure
2D structure of Chenodeoxycholic acid 3-glucuronide
CAS: 58814-71-4
CID: 20849182
Formula: C30H48O10
MW: 568.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight568.7
XLogP33.6
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Exact Mass568.32474772
Monoisotopic Mass568.32474772
Topological Polar Surface Area174 Ų
Heavy Atom Count40
Formal Charge0
Complexity959
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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