Structure Database (LMSD)

Common Name
TXB1
Systematic Name
9S,11,15S-trihydroxy-thrombox-13E-enoic acid
Synonyms
  • Thromboxane B1
LM ID
LMFA03030008
Formula
C20H36O6
Exact Mass
Calculate m/z
372.251191
Sum Composition
FA 20:2;O4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View MassBank spectra
View spectra on LIPID MAPS Standard Spectra DB
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Thromboxanes [FA0303]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]
Carbocyclic fatty acids [FA0114]

Biological Context

TXB1 is produced in small amounts when DGLA is added to washed suspensions of human platelets, while the major metabolism of this 1-series fatty acid is via 12-lipoxygenase.1 However, when co-incubated with amounts of ethanol often found in intoxicated humans, the metabolism of DGLA shifts to an enhanced production of TXB1.1 Urinary TXB1 or its metabolites may thus be a specific biomarker of prior ethanol abuse.

This information has been provided by Cayman Chemical

References

1. Manku, M.S., Oka, M., and Horrobin, D.F. Differential regulation of the formation of prostaglandins and related substances from arachidonic acid and from dihomogammalinolenic acid. I. Effects of ethanol. Prostaglandins Med. 3(2), 119-128 (1979).
1. Manku, M.S., Oka, M., and Horrobin, D.F. Differential regulation of the formation of prostaglandins and related substances from arachidonic acid and from dihomogammalinolenic acid. I. Effects of ethanol. Prostaglandins Med. 3(2), 119-128 (1979).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Metabolism of 8,11,14-eicosatrienoic acid in human platelets.,
Biochim Biophys Acta, 1976
Pubmed ID: 952987

String Representations

InChiKey (Click to copy)
JSDWWNLTJCCSAV-VZBVYBAISA-N
InChi (Click to copy)
InChI=1S/C20H36O6/c1-2-3-6-9-15(21)12-13-18-16(17(22)14-20(25)26-18)10-7-4-5-8-11-19(23)24/h12-13,15-18,20-22,25H,2-11,14H2,1H3,(H,23,24)/b13-12+/t15-,16-,17-,18+,20?/m0/s1
SMILES (Click to copy)
C(CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)OC(O)C[C@@H]1O)(=O)O

Other Databases

PubChem CID
71668258
Cayman ID
10006610

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 389.66
Topological Polar Surface Area 109.29
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 4.14
Molar Refractivity 101.67

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Created at
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Updated at
26th Aug 2024