Structure Database (LMSD)

Common Name
Etretinate
Systematic Name
Synonyms
  • (2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid ethyl ester
LM ID
LMPR01090046
Formula
C23H30O3
Exact Mass
Calculate m/z
354.219495
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Biological Context

Etretinate is a second-generation retinoid previously used systemically to manage psoriasis but withdrawn due to teratogenicity.1,2 Etretinate alters cAMP signaling, which may be defective in psoriasis.3,4

This information has been provided by Cayman Chemical

References

1. Hopkins, R., Bird, H.A., Jones, H., et al. A double-blind controlled trial of etretinate (Tigason) and ibuprofen in psoriatic arthritis. Ann. Rheum. Dis. 44(3), 189-193 (1985).
2. Isuka, H., Ohkuma, N., and Ohkawara, A. Effects of retinoids on the cyclic AMP system of pig skin epidermis. J. Invest. Dermatol. 85(4), 324-327 (1985).
3. Schopf, R.E., Langendorf, Y., Benz, R.E., et al. A highly decreased binding of cyclic adenosine monophosphate to protein kinase A in erythrocyte membranes is specific for active psoriasis. J. Invest. Dermatol. 119(1), 160-165 (2002).
4. Turton, J.A., Williars, G.B., Haselden, J.N., et al. Comparative teratogenicity of nine retinoids in the rat. Int. J. Exp. Path. 73(5), 551-563 (1992).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Etretinate therapy.,
J Am Acad Dermatol, 1987
Pubmed ID: 3546414

String Representations

InChiKey (Click to copy)
HQMNCQVAMBCHCO-DJRRULDNSA-N
InChi (Click to copy)
InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
SMILES (Click to copy)
C1(C)=C(C)C(/C=C/C(=C/C=C/C(=C/C(=O)OCC)/C)/C)=C(C)C=C1OC

Other Databases

Wikipedia
Etretinate
CHEBI ID
4913
LIPIDBANK ID
VVA0045
PubChem CID
5282375
Cayman ID
19878
GuidePharm ID
7599

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 1
Rotatable Bonds 8
Van der Waals Molecular Volume 388.45
Topological Polar Surface Area 35.53
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 3
logP 5.93
Molar Refractivity 110.02

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Created at
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Updated at
2nd Jul 2021