Structure Database (LMSD)

Common Name
tetranor-PGDM-d6
Systematic Name
9S-hydroxy-11,15-dioxo-2,3,4,5-tetranor-prostan-1,20-dioic-17,17,18,18,19,19-d6 acid
Synonyms
LM ID
LMFA03010252
Formula
Exact Mass
Calculate m/z
334.189866
Status
Curated

Classification

Biological Context

tetranor-PGDM-d6 contains six deuterium atoms at the 17, 17', 18, 18', 19 and 19' positions. It is intended for use as an internal standard for the quantification of tetranor-PGDM by GC- or LC-mass spectrometry (MS). Prostaglandin D2 (PGD2) is synthesized by hematopoietic-type PGD-synthase (H-PGDS) in mast cells and is released in large quantities during allergic and asthmatic anaphylaxis.1 PGD2 is also produced in the brain by lipocalin PGD-synthase also known as β-trace.2,3 In the brain, PGD2 produces normal physiological sleep and lowering of body temperature.2,3 Further pharmacological actions include inhibition of platelet aggregation and relaxation of vascular smooth muscle.4 tetranor-PGDM is a major metabolite of PGD2 that is detectable in human and murine urine.5 The levels of tetranor-PGDM and 2,3-dinor-11b-PGF2α, a related PGD2 metabolite, in human urine were found to be 1.5 ± 0.3 and 0.6 ± ng/mg creatinine, respectively. tetranor-PGDM was detected in mouse urine at a level of 8.1 ± 1.3 ng/mg creatinine.5

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
VNJBSPJILLFAIC-OSZDNXCMSA-N
InChi (Click to copy)
InChI=1S/C16H24O7/c17-10(3-1-2-4-15(20)21)5-6-11-12(7-8-16(22)23)14(19)9-13(11)18/h11-12,14,19H,1-9H2,(H,20,21)(H,22,23)/t11-,12-,14+/m1/s1/i1D2,2D2,4D2
SMILES (Click to copy)
[C@H]1(CCC(=O)CC([2H])([2H])C([2H])([2H])C([2H])([2H])C(=O)O)C(=O)C[C@H](O)[C@@H]1CCC(=O)O

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings
Rotatable Bonds 11
Van der Waals Molecular Volume 323.97
Topological Polar Surface Area 128.97
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 1.70
Molar Refractivity 80.34

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Created at
4th Dec 2024
Updated at
5th Dec 2024