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9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
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ChemBase ID:
72641
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Molecular Formular:
C21H26O3
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Molecular Mass:
326.42934
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Monoisotopic Mass:
326.18819469
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SMILES and InChIs
SMILES:
c1c(c(c(c(c1C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C)C)OC
Canonical SMILES:
COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
InChI:
InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+
InChIKey:
IHUNBGSDBOWDMA-AQFIFDHZSA-N
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Cite this record
CBID:72641 http://www.chembase.cn/molecule-72641.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
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(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
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IUPAC Traditional name
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acitretin
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(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
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Synonyms
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9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
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Acitretin
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Soriatane
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Acitretin
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(all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid
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Neotigason, Soriatane
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Neotigason
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Etretin
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CAS Number
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EC Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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5.011076
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H Acceptors
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3
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H Donor
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1
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LogD (pH = 5.5)
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4.976502
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LogD (pH = 7.4)
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3.2266924
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Log P
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5.5870485
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Molar Refractivity
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104.1665 cm3
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Polarizability
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38.030373 Å3
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Polar Surface Area
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46.53 Å2
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Rotatable Bonds
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6
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Lipinski's Rule of Five
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false
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DETAILS
DETAILS
Selleck Chemicals
Sigma Aldrich
TRC
Selleck Chemicals -
S1368
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Research Area: Inflammation Biological Activity: Acitretin is a second generation retinoid. It is taken orally, and is typically used for psoriasis. It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t1/2=120 days), making dosing difficult. In contrast, acitretin’s half-life is approximately 2 days. [1] |
Sigma Aldrich -
44707
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Biochem/physiol Actions Synthetic retinoid that is a metabolite of etretinate. Preferentially binds to cellular retinoic acid binding proteins (CRABPs). |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • http://en.wikipedia.org/wiki/Acitretin
- • Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
- • Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)
- • Ger. Pat., 1977, 2 636 879; CA, 87, 23565y, (synth, deriv)
- • Haenni, R. et al., Helv. Chim. Acta, 1977, 60, 2309, (synth, pmr, ms, metab)
- • Mayer, H. et al., Experientia, 1978, 34, 1105, (rev, pharmacol)
- • Englert, G. et al., Helv. Chim. Acta, 1978, 61, 2697, (pmr, isom)
- • Paravicini, U. et al., Ann. N.Y. Acad. Sci., 1981, 359, 54, (rev, metab)
- • Ward, A. et al., Drugs, 1983, 26, 9, (rev)
- • Bestmann, H.J. et al., Annalen, 1984, 1740, (isoetretin)
- • Cunliffe, W.J., Biochem. Soc. Trans., 1986, 14, 943, (props)
- • Coffey, J.W. et al., Int. Congr. Ser. Excerpta Med., 1987, 750, 705, (rev, isomers)
- • Jakobsen, P. et al., J. Chromatogr., 1987, 415, 413, (hplc)
- • Pilkington, T. et al., Drugs, 1992, 43, 597, (rev)
- • Bouvy, M.L. et al., Pharm. Weekbl., Sci. Ed., 1992, 14, 33, (Acitretin, rev, pharmacokinet)
- • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 754; 758
- • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EMJ500; REP400
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PATENTS
PATENTS
PubChem Patent
Google Patent