Structure Database (LMSD)

Common Name
all-trans-4-oxoretinoic acid
Systematic Name
Synonyms
LM ID
LMPR01090026
Formula
Exact Mass
Calculate m/z
314.188195
Status
Curated


Classification

Biological Context

4-oxo Retinoic acid is an active metabolite of the vitamin A metabolite and retinoic acid receptor (RAR) ligand all-trans retinoic acid .1 It is formed from all-trans retinoic acid by several cytochrome P450 (CYP) isoforms, including CYP1A1, CYP3A7, and CYP26A1.2,3 4-oxo Retinoic acid binds to RARα, RARβ, and RARγ (IC50s = 59, 50, and 142 nM, respectively, in radioligand binding assays) and induces expression of a luciferase reporter in COS-7 cells expressing RARα, RARβ, or RARγ (EC50s = 33, 8, and 89 nM, respectively).1 It increases protein levels of cytokeratin 7 (CK-7) and CK-19 in human epidermal keratinocytes when used at a concentration of 1 µM.4 4-oxo Retinoic acid (10-1,000 nM) inhibits the proliferation of MCF-7 breast cancer cells.5 It is teratogenic to zebrafish embryos (EC50 = 8.1 nM).6

This information has been provided by Cayman Chemical

References

1. 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).
4. Baron, J.M., Heise, R., Blaner, W.S., et al. Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J. Invest. Dermatol. 125(1), 143-153 (2005).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cricetulus griseus (#10029)
Mammalia (#40674)
Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver.,
Biochemistry, 1979
Pubmed ID: 435468

String Representations

InChiKey (Click to copy)
GGCUJPCCTQNTJF-FRCNGJHJSA-N
InChi (Click to copy)
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
SMILES (Click to copy)
C1C(C)(C)C(/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)=C(C)C(=O)C1

Other Databases

KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
VVA0025
PubChem CID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 350.09
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 4.78
Molar Refractivity 94.15

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Created at
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Updated at
21st Dec 2022