Structure Database (LMSD)

OH O O O HO HO OH H H H H HO O
Common Name
Lithocholic acid 3-O-glucuronide
Systematic Name
3α-(β-D-glucopyranuronosyloxy)-5β-cholan-24-oic acid
Synonyms
  • Lithocholate 3-O-glucuronide
LM ID
LMST05010066
Formula
C30H48O9
Exact Mass
Calculate m/z
552.329835
Sum Composition
ST 24:1;O3;GlcA
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Glucuronides [ST0501]
Bile acids and derivatives [ST04]
C24 bile acids, alcohols, and derivatives [ST0401]

String Representations

InChiKey (Click to copy)
GIQXKAXWRLHLDD-VYACWCJYSA-N
InChi (Click to copy)
InChI=1S/C30H48O9/c1-15(4-9-22(31)32)19-7-8-20-18-6-5-16-14-17(10-12-29(16,2)21(18)11-13-30(19,20)3)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h15-21,23-26,28,33-35H,4-14H2,1-3H3,(H,31,32)(H,36,37)/t15-,16-,17-,18+,19-,20+,21+,23+,24+,25-,26+,28-,29+,30-/m1/s1
SMILES (Click to copy)
C1C[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@H]([C@H](C)CCC(=O)O)CC[C@@]4([H])[C@]3([H])CC[C@]2([H])C[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Bile salt glucuronides: identification and quantitative analysis in the urine of patients with cholestasis.,
Eur J Clin Invest, 1976
Pubmed ID: 1253809

Other Databases

KEGG ID
C03033
HMDB ID
HMDB0002513
CHEBI ID
137921
PubChem CID
126511

Calculated Physicochemical Properties

Heavy Atoms 39
Rings 5
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 539.59
Topological Polar Surface Area 155.82
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 9
logP 5.14
Molar Refractivity 143.51

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Created at
-
Updated at
27th Jun 2019