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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:13:17 UTC
HMDB IDHMDB0014997
Secondary Accession Numbers
  • HMDB14997
Metabolite Identification
Common NamePenicillamine
DescriptionPenicillamine is only found in individuals that have used or taken this drug. It is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. [PubChem]Penicillamine is a chelating agent recommended for the removal of excess copper in patients with Wilson's disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cystine and is excreted readily. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.
Structure
Thumb
Synonyms
ValueSource
(+-)-PenicillamineChEBI
2-amino-3-mercapto-3-Methylbutyric acidChEBI
3,3-DimethylcysteineChEBI
beta-MercaptovalineChEBI
D,L-PenicillamineChEBI
DL-3-MercaptovalineChEBI
DL-beta-MercaptovalineChEBI
2-amino-3-mercapto-3-MethylbutyrateGenerator
b-MercaptovalineGenerator
β-mercaptovalineGenerator
DL-b-MercaptovalineGenerator
DL-β-mercaptovalineGenerator
beta,beta-DimethylcysteineHMDB
beta-ThiovalineHMDB
D-MercaptovalineHMDB
D-PenamineHMDB
D-PenicilamineHMDB
D-PenicillamineHMDB
D-PenicyllamineHMDB
DimethylcysteineHMDB
L-PenicillamineHMDB
PenicillaminHMDB
PenicillaminaHMDB
PenicilllamineHMDB
Chemical FormulaC5H11NO2S
Average Molecular Weight149.211
Monoisotopic Molecular Weight149.051049291
IUPAC Name2-amino-3-methyl-3-sulfanylbutanoic acid
Traditional Name(+-)-penicillamine
CAS Registry Number52-67-5
SMILES
CC(C)(S)C(N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)
InChI KeyVVNCNSJFMMFHPL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid
  • Branched fatty acid
  • Thia fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point198.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.65 g/LNot Available
LogP-1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.65 g/LALOGPS
logP-1.7ALOGPS
logP-2.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.56ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.22 m³·mol⁻¹ChemAxon
Polarizability14.88 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-53220ef4bf765d5867dcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fka-9500000000-e42c54b7496cbff2d761View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-5ce6ffc67f24493fa02aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-5900000000-ac76f8c72b2335916905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-2211209d297edcae5f72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0900000000-9a13581ec86df368b000View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-4c84239071ebf03d19f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9100000000-13c27853348bf51a69c1View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00859 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00859 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4565
KEGG Compound IDC07418
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPenicillamine
METLIN IDNot Available
PubChem Compound4727
PDB IDNot Available
ChEBI ID50868
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. [PubMed:9117147 ]
  2. Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. [PubMed:10796440 ]
  3. Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. [PubMed:12889074 ]
  4. WALSHE JM: Penicillamine, a new oral therapy for Wilson's disease. Am J Med. 1956 Oct;21(4):487-95. [PubMed:13362281 ]
  5. Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. [PubMed:15495127 ]
  6. Duruelo J, Cuende E, Preciado E, Diaz de Otazu R, Vesga JC: [Microscopic polyangiitis in a patient with systemic sclerosis]. Reumatol Clin. 2005 Oct;1(3):177-9. doi: 10.1016/S1699-258X(05)72739-X. Epub 2008 Dec 20. [PubMed:21794259 ]
  7. Masson MJ, Teranishi M, Shenton JM, Uetrecht JP: Investigation of the involvement of macrophages and T cells in D-penicillamine-induced autoimmunity in the Brown Norway rat. J Immunotoxicol. 2004 Apr;1(2):79-93. doi: 10.1080/15476910490496258. [PubMed:18958641 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Gui C, Hagenbuch B: Role of transmembrane domain 10 for the function of organic anion transporting polypeptide 1B1. Protein Sci. 2009 Nov;18(11):2298-306. doi: 10.1002/pro.240. [PubMed:19760661 ]