D-penicillamine (CHEBI:7959)

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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

Average Mass

149.21100

Monoisotopic Mass

149.05105

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):	copper chelator A chelator that is any compound containing a ligand (typically organic) which is able to form a bond to a central copper atom at two or more points. 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 )

Biological Role(s):	drug allergen Any drug which causes the onset of an allergic reaction.

Application(s):	drug allergen Any drug which causes the onset of an allergic reaction. antirheumatic drug A drug used to treat rheumatoid arthritis.

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) has role copper chelator (CHEBI:166831) D-penicillamine (CHEBI:7959) has role drug allergen (CHEBI:88188) 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

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

Last Modified

12 November 2020