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Penicillamine

Athanor · official

C5H11NO2S · 149.21 g/mol

IUPAC name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

Also called Cuprimine, Depen, D-penicillamine, Wilson disease

Amino acidsDrugs
Open in Athanor
The structure of Penicillamine
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
Synonyms
Cuprimine, Depen, D-penicillamine
+ 37 more

Wilson disease, D-Penicillamine, D-(-)-Penicillamine, 3-Mercapto-D-valine, (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid, (-)-Penicillamine, Cuprenil, Cupripen, D-Valine, 3-mercapto-, Kuprenil, Trolovol, (S)-3,3-Dimethylcysteine, Mercaptovaline, Penicilamina, D-3-Mercaptovaline, Penicillaminum, D-beta,beta-Dimethylcysteine, Penicillamina, Sufortan, (S)-2-amino-3-mercapto-3-methylbutanoic acid, Dimethylcysteine, beta,beta-Dimethylcysteine, DTXSID6037069, GNN1DV99GX, Distamine, CHEBI:7959, NSC-81549, DTXCID4017069, NSC81549, D Penicillamine, D 3 Mercaptovaline, Penicillaminate, Copper, beta,beta Dimethylcysteine, Kelatin, Atamir, D Mercaptovaline, RefChem:55825

Molecular formula
C5H11NO2S
Empirical formula
C5H11NO2S
Molecular weight
149.21 g/mol
Exact mass
149.05105
CAS number
52-67-5
PubChem CID
5852
Canonical SMILES
CC(C)(C(C(=O)O)N)S
Isomeric SMILES
CC(C)([C@H](C(=O)O)N)S
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
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

Appearance
FINE, WHITE OR PRACTICALLY WHITE, CRYSTALLINE POWDER[1]
Odor
SLIGHT CHARACTERISTIC ODOR[1]
Solubility in water
FREELY SOL IN WATER; SLIGHTLY SOL IN ALC; INSOL IN ETHER, CHLOROFORM.[1]

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
9
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.8
H-bond donors
3
H-bond acceptors
3 computed here · PubChem 4
Rotatable bonds
2
TPSA (Ų)
63.3 computed here · PubChem 64.3
Formal charge
0
XLogP3
-1.8 PubChem
Complexity
124 PubChem
Stereocenters
1 definedCIP: C5: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C40.25%
  • H7.43%
  • N9.39%
  • O21.44%
  • S21.49%

Isotope pattern

100%149.0516.8%150.0545.1%151.048152.051

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
0.11 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-0.7 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.4 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 149.22
  • log P ≤ 5 (Crippen): 0.11
  • H-bond donors ≤ 5: 3
  • H-bond acceptors ≤ 10: 3

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 52 company reports to ECHA. Source [2].

  • Harmful or irritant
  • H315Causes skin irritation (90.4% of reports)
  • H319Causes serious eye irritation (88.5% of reports)
  • H335May cause respiratory irritation (84.6% of reports)

Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Storage

  • Packaging and storage: Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a tight container. (penicillamine capsules USP)[1]
  • Packaging and storage: Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Store in a tight container. (penicillamine tablets USP)[1]

Safety data sheets on the supplier’s page: CymitQuimica, Sigma-Aldrich, AbaChemScene.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  2. [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  3. [3]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  4. [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  7. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  8. ·Literature on PubChem

Data last updated 2026-10-14.