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
3D model of Tauro-omega-muricholic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
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
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
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