Structure Database (LMSD)

Common Name
2,3-Dinor-TXB1
Systematic Name
9S,11,15S-trihydroxy-2,3-dinor-thrombox-13E-en-1-oic acid
Synonyms
  • 2,3-Dinor-Thromboxane B1
LM ID
LMFA03030012
Formula
C18H32O6
Exact Mass
Calculate m/z
344.219891
Sum Composition
FA 18:2;O4
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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

In rats and rabbits, 2,3-dinor TXB1 has been identified as another urinary metabolite of TXB2.1,2 However in human urine, only trace amounts of 2,3-dinor TXB1 have been identified.1 In rats, 2,3-dinor TXB1 is excreted at a much higher rate than 2,3-dinor TXB2 (19.2 ± 4.9 ng/24 hr and 1.6 ± 0.3 ng/24 hr, respectively).1 Therefore, urinary 2,3-dinor TXB1 is a suitable marker of thromboxane biosynthesis in rats.

This information has been provided by Cayman Chemical

References

1. Chiabrando, C., Corada, M., Bachi, A., et al. Urinary excretion of 2,3-dinor-thromboxane B1, a major metabolite of thromboxane B2 in the rat. Prostaglandins 47, 409-422 (1994).
1. Chiabrando, C., Corada, M., Bachi, A., et al. Urinary excretion of 2,3-dinor-thromboxane B1, a major metabolite of thromboxane B2 in the rat. Prostaglandins 47, 409-422 (1994).
2. Westlund, P., Kumlin, M., Nordenström, A., et al. Circulating and urinary thromboxane B2 metabolites in the rabbit: 11-dehydro-thromboxane B2 as parameter of thromboxane production. Prostaglandins 31(3), 413-443 (1986).
2. Westlund, P., Kumlin, M., Nordenström, A., et al. Circulating and urinary thromboxane B2 metabolites in the rabbit: 11-dehydro-thromboxane B2 as parameter of thromboxane production. Prostaglandins 31(3), 413-443 (1986).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Rattus norvegicus (#10116)
Mammalia (#40674)
Urinary excretion of 2,3-dinor-thromboxane B1, a major metabolite of thromboxane B2 in the rat.,
Prostaglandins, 1994
Pubmed ID: 7938613

String Representations

InChiKey (Click to copy)
LGWCOUWMTAQMQT-QCBHMXSDSA-N
InChi (Click to copy)
InChI=1S/C18H32O6/c1-2-3-4-7-13(19)10-11-16-14(8-5-6-9-17(21)22)15(20)12-18(23)24-16/h10-11,13-16,18-20,23H,2-9,12H2,1H3,(H,21,22)/b11-10+/t13-,14-,15-,16+,18?/m0/s1
SMILES (Click to copy)
C1[C@H](O)[C@H](CCCCC(=O)O)[C@@H](/C=C/[C@@H](O)CCCCC)OC1O

Other Databases

CHEBI ID
165348
PubChem CID
101668701
Cayman ID
10006330

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 1
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 355.06
Topological Polar Surface Area 109.29
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 3.36
Molar Refractivity 92.43

Admin

Created at
-
Updated at
21st Nov 2024