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52-67-5 molecular structure
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(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

ChemBase ID: 179831
Molecular Formular: C5H11NO2S
Molecular Mass: 149.21134
Monoisotopic Mass: 149.0510496
SMILES and InChIs

SMILES:
[C@@H](C(=O)O)(C(S)(C)C)N
Canonical SMILES:
N[C@@H](C(S)(C)C)C(=O)O
InChI:
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)
InChIKey:
VVNCNSJFMMFHPL-UHFFFAOYSA-N

Cite this record

CBID:179831 http://www.chembase.cn/molecule-179831.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
IUPAC Traditional name
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
depen
Synonyms
D-Penicillamine
Depen
Distamine
D-Mercaptovaline
D-Penamine
Kuprenil
Penicillamine (Cuprimine)
CAS Number
52-67-5
PubChem SID
164235741
PubChem CID
92863

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 92863 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.555553  H Acceptors
H Donor LogD (pH = 5.5) -2.1465738 
LogD (pH = 7.4) -2.1542492  Log P -2.1465182 
Molar Refractivity 37.225 cm3 Polarizability 15.067698 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Pharmacology Properties Product Information Bioassay(PubChem)
Target
Others expand Show data source
Mechanism of Action
a substance that is much more soluble than cystine and is excreted readily. expand Show data source
Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity. expand Show data source
Chelating agent recommended for the removal of excess copper in patients with Wilson's disease. expand Show data source
From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. expand Show data source
Penicillamine also reduces excess cystine excretion in cystinuria. expand Show data source
Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. expand Show data source
The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. expand Show data source
This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, expand Show data source
Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. expand Show data source
Salt Data
Free Base expand Show data source
Application(s)
Antiinflammatory expand Show data source
Antirheumatic expand Show data source
Chelating agent used in therapy of metal poisoning, and for Wilson's disease, scleroderma and rheumatoid arthritis expand Show data source

DETAILS

DETAILS

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • ldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 592B; 592C; 592D; 787A, (ir)
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 892B; 1282C, (nmr)
  • • Sadtler Standard NMR Spectra, 2305, (pmr)
  • • Ss, O., Annalen, 1948, 559, 92, (synth)
  • • Ruiz-Torres, Arzneim.-Forsch., 1974, 24, 914, (pharmacol, metab)
  • • Rosenfield, R.E. et al., Acta Cryst. B, 1975, 31, 462, (cryst struct, abs config)
  • • Weigert, W.M. et al., Angew. Chem., Int. Ed., 1975, 14, 330, (rev)
  • • Parrett, D., Proc. R. Soc. Med., 1977, 70, 61, (metab)
  • • Jaffe, I.A., Pharmacol. Biochem. Prop. Drug Subst., 1979, 1, 465, (rev, pharmacol)
  • • Chiu, C.C. et al., Anal. Profiles Drug Subst., 1981, 10, 601, (rev, synth, prop, tox, pharmacol)
  • • Parrett, D. et al., J. Rheumatol. Suppl., 1981, 7, 28, (rev)
  • • Scheinberg, I.H. et al., Wilson's Disease, W.B. Saunders, 1984, 126, (use, pharmacol)
  • • Busker, E. et al., J. Chromatogr., 1985, 350, 179, (sepn)
  • • Nether, P. et al., Clin. Pharmacokinet., 1987, 13, 317, (pharmacol)
  • • Wolf-Heuss, E.M., Methods Enzymol., 1987, 143, 186, (rev, detn)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 346
  • • Ogawa, T. et al., Chem. Pharm. Bull., 1988, 36, 1957; 1989, 37, 1609, (synth)
  • • Van der Korst, J.K. et al., Inflammatory Dis. Ther., 1992, 9, 203, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 688
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCR750; PAP500; PAP550
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