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Structure Database (LMSD)

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Common Name

Chenodeoxycholic acid 3-glucuronide

Systematic Name

(3α,5β,7α)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-β-D-Glucopyranosiduronic acid

Synonyms

LM ID

LMST05010028

Formula

C₃₀H₄₈O₁₀

Exact Mass

Calculate m/z

568.32475

Sum Composition

ST 24:1;O4;GlcA

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Chenodeoxycholic acid 3-glucuronide (CDCA-3G) is a metabolite of CDCA .^1,2 It is formed from CDCA in human liver microsomes.

This information has been provided by Cayman Chemical

References

1. Caron, P., Trottier, J., Verreault, M., et al. Enzymatic production of bile acid glucuronides used as analytical standards for liquid chromatography-mass spectrometry analyses. Mol. Pharm. 3(3), 293-302 (2006).

2. Takehara, I., Terashima, H., Nakayama, T., et al. Investigation of glycochenodeoxycholate sulfate and chenodeoxycholate glucuronide as surrogate endogenous probes for drug interaction studies of OATP1B1 and OATP1B3 in healthy Japanese volunteers. Pharm. Res. 34(8), 1601-1614 (2017).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Bile acid glucuronides, II[1]. Isolation and identification of a chenodeoxycholic acid glucuronide from human plasma in intrahepatic cholestasis,
Hoppe Seylers Z Physiol Chem, 1976

Pubmed ID: 1254247

String Representations

InChiKey (Click to copy)

GDNGOAUIUTXUES-BWGRGVIUSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

O([C@H]1C[C@@]2([H])C[C@@H](O)[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@](C)([H])CCC(=O)O)[C@@]4(C)CC[C@]3([H])[C@@]2(C)CC1)[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](C(=O)O)O1)O