Structure Database (LMSD)

Common Name
Tetranor-PGE1
Systematic Name
2,3,4,5-tetranor-9-oxo-11R,15S-dihydroxy-13E-prostenoic acid
Synonyms
  • Tetranor-PGE2
LM ID
LMFA03010211
Formula
C16H26O5
Exact Mass
Calculate m/z
298.178025
Sum Composition
FA 16:3;O3
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]
Prostaglandins [FA0301]

Biological Context

tetranor-Prostaglandin E1 (tetranor-PGE1) is metabolite of PGE1 and PGE2 that is formed by β-oxidation.1,2

This information has been provided by Cayman Chemical

References

1. Oates, J.A., Sweetman, B.J., Gréene, K., et al. Identification and assay of tetranor-prostaglandin E1 in human urine. Anal. Biochem. 74(2), 546-559 (1976).
2. Kimbrough, J.R., Jana, S., Kim, K., et al. Synthesis of tetranor-PGE1: A urinary metabolite of prostaglandins E1 and E2. Tetrahedron Lett. 61(22), 151922 (2020).

String Representations

InChiKey (Click to copy)
FPTFFTMXBKQFKC-JZKKULJYSA-N
InChi (Click to copy)
InChI=1S/C16H26O5/c1-2-3-4-5-11(17)6-7-12-13(8-9-16(20)21)15(19)10-14(12)18/h6-7,11-14,17-18H,2-5,8-10H2,1H3,(H,20,21)/b7-6+/t11-,12+,13+,14+/m0/s1
SMILES (Click to copy)
C(C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)CC1=O)C(O)=O

Other Databases

CHEBI ID
165344
PubChem CID
6449794
Cayman ID
26702

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 309.03
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 2.49
Molar Refractivity 79.79

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Updated at
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