Structure Database (LMSD)

Common Name
all-trans-4-hydroxyretinoic acid
Systematic Name
Synonyms
LM ID
LMPR01090025
Formula
C20H28O3
Exact Mass
Calculate m/z
316.203845
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Prenol Lipids [PR]
Isoprenoids [PR01]
Retinoids [PR0109]

Biological Context

all-trans-4-hydroxy Retinoic acid is a metabolite of all-trans retinoic acid formed by the cytochrome P450 (CYP) isoforms CYP26A1, B1, and C1.1,2 It binds to retinoic acid receptors (RARs) with a lower affinity than other all-trans retinoic acid metabolites (IC50s = 606, 298, and 892 nM for RARα, RARβ, and RARγ, respectively, in a radioligand binding assay). It also transactivates RARs with a lower efficacy than other metabolites (EC50s = 791, 64, and 94 nM for RARα, RARβ, and RARγ, respectively) but induces transcription of a reporter plasmid equipotently. all-trans-4-hydroxy Retinoic acid inhibits cell growth, halts the cell cycle in the G1 phase, and induces differentiation of NB4 acute promyelocytic leukemia cells (EC50 = 79.8 nM).3

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. J. Biol. Chem. 277(25), 31491-31498 (2002).
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).
3. Taimi, M., Helvig, C., Wisniewski, J., et al. A novel human cytochrome P450, CYP26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. J. Biol. Chem. 279(1), 77-85 (2004).

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)
KGUMXGDKXYTTEY-FRCNGJHJSA-N
InChi (Click to copy)
InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,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
C16677
HMDB ID
HMDB0006254
CHEBI ID
63795
LIPIDBANK ID
VVA0024
PubChem CID
6438629
Cayman ID
21378

Calculated Physicochemical Properties

Heavy Atoms 23
Rings 1
Aromatic Rings 0
Rotatable Bonds 5
Van der Waals Molecular Volume 352.73
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.86
Molar Refractivity 95.66

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Created at
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Updated at
21st Dec 2022