CHEBI:7959 - D-penicillamine

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ChEBI Name D-penicillamine
ChEBI ID CHEBI:7959
ChEBI ASCII Name D-penicillamine
Definition An optically active form of penicillamine having D-configuration. Pharmaceutical form (L-form is toxic) of chelating agent used to treat heavy metal poisoning.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:469179
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Formula C5H11NO2S
Net Charge 0
Average Mass 149.21100
Monoisotopic Mass 149.051
InChI InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChIKey VVNCNSJFMMFHPL-VKHMYHEASA-N
SMILES CC(C)(S)[C@@H](N)C(O)=O
Roles Classification
Chemical Role(s): chelator
A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): antirheumatic drug
A drug used to treat rheumatoid arthritis.
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ChEBI Ontology
Outgoing D-penicillamine (CHEBI:7959) has role antirheumatic drug (CHEBI:35842)
D-penicillamine (CHEBI:7959) has role chelator (CHEBI:38161)
D-penicillamine (CHEBI:7959) is a non-proteinogenic α-amino acid (CHEBI:83925)
D-penicillamine (CHEBI:7959) is a penicillamine (CHEBI:50868)
D-penicillamine (CHEBI:7959) is enantiomer of L-penicillamine (CHEBI:50869)
Incoming benzylpenillamine (CHEBI:61224) has functional parent D-penicillamine (CHEBI:7959)
L-penicillamine (CHEBI:50869) is enantiomer of D-penicillamine (CHEBI:7959)
IUPAC Names
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
3-sulfanyl-D-valine
INNs Sources
penicilamina ChemIDplus
pénicillamine WHO MedNet
penicillamine KEGG DRUG
penicillaminum ChemIDplus
Synonyms Sources
(−)-penicillamine ChemIDplus
(S)-2-amino-3-mercapto-3-methylbutanoic acid ChEMBL
(S)-3,3-dimethylcysteine ChemIDplus
3-mercapto-D-valine ChemIDplus
D-(−)-penicillamine ChemIDplus
D-β,β-dimethylcysteine NIST Chemistry WebBook
PA ChEBI
Brand Names Sources
Cuprimine KEGG DRUG
D-Penamine NIST Chemistry WebBook
Depen KEGG DRUG
Manual Xrefs Databases
2081 DrugCentral
C07418 KEGG COMPOUND
D00496 KEGG DRUG
DB00859 DrugBank
HMDB0014997 HMDB
LEI PDBeChem
Penicillamine Wikipedia
View more database links
Registry Numbers Types Sources
1722375 Reaxys Registry Number Reaxys
1722375 Beilstein Registry Number Beilstein
52-67-5 CAS Registry Number KEGG COMPOUND
52-67-5 CAS Registry Number NIST Chemistry WebBook
52-67-5 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017