Chemical substance record

D-penicillamine

52-67-5C₅H₁₁NO₂S149.215 g/mol

Organic/Inorganic Small MoleculeChEBI source record

An optically active form of penicillamine having D-configuration. Pharmaceutical form (L-form is toxic) of chelating agent used to treat heavy metal poisoning. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	52-67-5	ChEBI ↗
Molecular formula	C₅H₁₁NO₂S	ChEBI ↗
Molar mass	149.215 g/mol	ChEBI ↗
Monoisotopic mass	149.05105 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:7959	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	149.21 g/mol	PubChem ↗
Exact mass	149.05104977 Da	PubChem ↗
Computed XLogP	-1.8	PubChem ↗
Topological polar surface area (Å²)	64.3	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	4	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

D-penicillamine

IUPAC name

(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

InChIKey

VVNCNSJFMMFHPL-VKHMYHEASA-N

SMILES

CC(C)(S)[C@@H](N)C(=O)O

InChI

InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

Names & synonyms

(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid3-sulfanyl-D-valineCuprimineD-PenamineDepenpenicilaminapenicillaminepenicillaminum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

penicillamineChEBI parent class · 50868 ↗non-proteinogenic alpha-amino acidChEBI parent class · 83925 ↗

carboxylic acid amino acid organosulfur compound organic molecular entity

Roles recorded in ChEBI

copper chelatorantirheumatic drugchelatordrug allergen

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00670174 mol

Uses 149.215 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 5 atoms

40.25%

S

Sulfur · 1 atom

21.49%

O

Oxygen · 2 atoms

21.44%

N

Nitrogen · 1 atom

9.39%

H

Hydrogen · 11 atoms

7.43%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

T cell responses to D-penicillamine in drug-induced myasthenia gravis: recognition of modified DR1:peptide complexes. ↗Journal of neuroimmunology · 1999 Jun 1 · PMID 10408968

Metabolism in vitro of the sulphydryl amino acids, L- and D-penicillamine. ↗Biochemical pharmacology · 1959 Dec · PMID 13793949

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:7959

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 5852 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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