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Structure Database (LMSD)

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Common Name

all-trans-5,6-Epoxyretinoic acid

Systematic Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

Synonyms

LM ID

LMPR01090055

Formula

C₂₀H₂₈O₃

Exact Mass

Calculate m/z

316.203846

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

all-trans-5,6-epoxy Retinoic acid (5,6-epoxy RA) is an agonist of all isoforms of the retinoic acid receptor (RAR; EC50s = 77, 35, and 4 nM for RARα, RARβ, and RARγ, respectively).¹ 5,6-epoxy RA (1 µM) also induces growth arrest of MCF-7 and NB4 cells in vitro.^2,3 It is a natural metabolite of all-trans retinoic acid , which is a metabolite of vitamin A.⁴

This information has been provided by Cayman Chemical

References

1. McCormick, A.M., and Napoli, J.L. Identification of 5,6-epoxyretinoic acid as an endogenous retinol metabolite. The Journal of Biological Chemisty 257(4), 1730-1735 (1982).

2. Idrest, N., Marill, J., Flexor, M.A., et al. Activation of retinoic acid receptor-dependent transcription by all-trans-retinoic acid metabolites and isomers. The Journal of Biological Chemisty 277(25), 31491-31498 (2002).

3. Van heusden, J., Wouters, W., Ramaekers, F.C.S., et al. All-trans-retinoic acid metabolites significantly inhibit the proliferation of MCF-7 human breast cancer cells in vitro. Br. J. Cancer 77(1), 26-32 (1998).

4. Idres, N., Benoît, G., Flexor, M.A., et al. Granulocytic differentiation of human NB4 promyelocytic leukemia cells induced by all-trans retinoic acid metabolites. Cancer Res. 61(2), 700-705 (2001).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Rattus norvegicus (#10116)

Mammalia (#40674)

Identification of 5,6-epoxyretinoic acid as an endogenous retinol metabolite.,
J Biol Chem, 1982

Pubmed ID: 7056740

String Representations

InChiKey (Click to copy)

KEEHJLBAOLGBJZ-WEDZBJJJSA-N

InChi (Click to copy)

InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

SMILES (Click to copy)

C12(OC1(C)CCCC2(C)C)/C=C/C(/C)=C/C=C/C(/C)=C/C(=O)O