Structure Database (LMSD)

Common Name
Glycodehydrocholic acid
Systematic Name
N-(3,7,12-trioxo-5β-cholan-24-oyl)-glycine
Synonyms
  • GDHCA
  • N-[(5beta)-3,7,12,24-tetraoxocholan-24-yl]-glycine
  • glycine dehydrocholate
LM ID
LMST05030022
Formula
C26H37NO6
Exact Mass
Calculate m/z
459.262089
Sum Composition
ST 24:4;O4;Gly
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Glycine conjugates [ST0503]
Bile acids and derivatives [ST04]
C24 bile acids, alcohols, and derivatives [ST0401]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Triketocholanoic (dehydrocholic) acid. Hepatic metabolism and effect on bile flow and biliary lipid secretion in man.,
J Clin Invest, 1973
Pubmed ID: 4685091

String Representations

InChiKey (Click to copy)
ZDPYMJNWJWJTAF-HHELISEZSA-N
InChi (Click to copy)
InChI=1S/C26H37NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-15,17-19,24H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,17-,18+,19+,24+,25+,26-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC(=O)[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(NCC(=O)O)=O)CC[C@@]4([H])[C@]3([H])C(=O)C[C@]2([H])CC(=O)C1

Other Databases

CHEBI ID
166731
PubChem CID
13955640

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 459.46
Topological Polar Surface Area 117.61
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 3.47
Molar Refractivity 120.54

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Created at
1st Mar 2024
Updated at
24th Apr 2024