Structure Database (LMSD)

Common Name
Tauro-omega-muricholic acid
Systematic Name
N-(3α,6α,7β-Trihydroxy-5β-cholan-24-oyl)-taurine
Synonyms
  • TOMCA
  • T-omega-MCA
LM ID
LMST04010473
Formula
Exact Mass
Calculate m/z
515.291676
Sum Composition
Status
Curated

Classification

Biological Context

Tauro-ω-muricholic acid is a taurine-conjugated form of the secondary bile acid ω-muricholic acid . Hepatic levels of tauro-ω-muricholic acid are decreased in mice following a diet supplemented with cholic, deoxycholic, chenodeoxycholic, or ursodeoxycholic acid and in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD).1,2 Tauro-ω-muricholic acid is the predominant rare bile acid found in the serum of infants with early-onset neonatal sepsis.3

This information has been provided by Cayman Chemical

References

1. Zöhrer, E., Meinel, K., Fauler, G., et al. Neonatal sepsis leads to early rise of rare serum bile acid tauro-omega-muricholic acid (TOMCA). Pediatr. Res. 84(1), 66-70 (2018).
3. Zhang, Y., and Klaassen, C.D. Effects of feeding bile acids and a bile acid sequestrant on hepatic bile acid composition in mice. J. Lipid Res. 51(11), 3230-3242 (2010).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Neonatal sepsis leads to early rise of rare serum bile acid tauro-omega-muricholic acid (TOMCA).,
Pediatr Res, 2018
Pubmed ID: 29795204

String Representations

InChiKey (Click to copy)
XSOLDPYUICCHJX-SYCKBGHMSA-N
InChi (Click to copy)
InChI=1S/C26H45NO7S/c1-15(4-7-21(29)27-12-13-35(32,33)34)17-5-6-18-22-19(9-11-25(17,18)2)26(3)10-8-16(28)14-20(26)23(30)24(22)31/h15-20,22-24,28,30-31H,4-14H2,1-3H3,(H,27,29)(H,32,33,34)/t15-,16-,17-,18+,19+,20+,22+,23-,24-,25-,26-/m1/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCC(NCCS(O)(=O)=O)=O)CC[C@@]4([H])[C@]3([H])[C@@H](O)[C@H](O)[C@]2([H])C[C@H](O)C1

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 4
Aromatic Rings
Rotatable Bonds 7
Van der Waals Molecular Volume 497.32
Topological Polar Surface Area 144.16
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 8
logP 5.05
Molar Refractivity 134.25

Admin

Created at
27th Feb 2024
Updated at
24th Apr 2024