D-Penicillamine (CED0002666)

Record Information
Version1.0
Creation Date2016-05-22 04:23:23 UTC
Update Date2026-05-14 16:50:57 UTC
Accession NumberCHEM017477
Identification
Common NameD-Penicillamine
ClassSmall Molecule
Description
D-Penicillamine is an organic compound with the formula C5H11NO2S and an average molecular weight of 149.21 g/mol. D-Penicillamine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. The substance is found in or released from 12 recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics as well as antiinflammatory and antirheumatic products. Other sources include electrical and electronic equipment, specifically antennas, amplifiers, and adjustable resistors. Additionally, it is linked to building and construction materials, including floors, ladders, roofs, fencing, sunshades awnings or outside screens, and two other sources. Recorded routes of exposure for this compound include oral and inhalation.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-PenicillamineChEBI
(S)-2-Amino-3-mercapto-3-methylbutanoic acidChEBI
(S)-3,3-DimethylcysteineChEBI
3-Mercapto-D-valineChEBI
CuprimineChEBI
D-(-)-PenicillamineChEBI
D-beta,beta-DimethylcysteineChEBI
D-PenamineChEBI
DepenChEBI
PAChEBI
PenicilaminaChEBI
PenicillaminumChEBI
(S)-2-Amino-3-mercapto-3-methylbutanoateGenerator
D-b,b-DimethylcysteineGenerator
D-Β,β-dimethylcysteineGenerator
CuprenilMeSH
DimethylcysteineMeSH
Penicillaminate, copperMeSH
D PenicillamineMeSH
MetalcaptaseMeSH
D 3 MercaptovalineMeSH
MercaptovalineMeSH
beta,beta-DimethylcysteineMeSH
Copper penicillaminateMeSH
D-3-MercaptovalineMeSH
beta,beta DimethylcysteineMeSH
PenicillamineChEBI
Chemical FormulaC5H11NO2S
Average Molecular Mass149.211 g/mol
Monoisotopic Mass149.051 g/mol
CAS Registry Number52-67-5
IUPAC Name(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
Traditional Namedepen
SMILES[H][C@](N)(C(O)=O)C(C)(C)S
InChI IdentifierInChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChI KeyVVNCNSJFMMFHPL-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives 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
  • D-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Thia fatty acid
  • Fatty acyl
  • Fatty acid
  • Amino acid
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability14.76 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0fr5-1930000000-6ee8522d7087601d49e6Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-9520000000-1ac6006c4f882c72292bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-9640000000-736237ccaaa4ef171daaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-1900000000-ca3b0f005a0900197cf7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ufr-7900000000-bad3a6cc0c32a1b4493cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9100000000-9f0f7aaf661aaceff17cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-0900000000-3e88f7f9375f31828829Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-3900000000-2f3ec3dbefe757ef98d8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-9100000000-455730a935564d9415d5Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1489.0Log mg/kg[840:2600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
363Antiinflammatory and antirheumatic productsHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Penicillamine Drug Metabolism Action Pathway
Penicillamine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSuccinyl-diaminopimelate desuccinylaseP44514Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)Predicted (SEA)0.155698
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)2.33548
Metabotropic glutamate receptor 2 structureClick to view 3D structureMetabotropic glutamate receptor 2Q14416HumansPredicted (SEA)37.0562
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P39086HumansPredicted (SEA)5.2159
Click to view 3D structureMetabotropic glutamate receptor 2P31421Rattus norvegicusPredicted (SEA)32.3074
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP04825Escherichia coli (strain K12)Predicted (SEA)1.40129
Click to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)9.6533
Click to view 3D structureMetabotropic glutamate receptor 3P31422Rattus norvegicusPredicted (SEA)16.6597
Click to view 3D structureMetabotropic glutamate receptor 6O15303HumansPredicted (SEA)15.1027
Click to view 3D structureGlutamate transporter homologO59010Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)Predicted (SEA)3.73676
Excitatory amino acid transporter 3 structureClick to view 3D structureExcitatory amino acid transporter 3P43005HumansPredicted (SEA)15.2584
Click to view 3D structureMetabotropic glutamate receptor 6P35349Rattus norvegicusPredicted (SEA)10.3539
Click to view 3D structureGlutamate receptor ionotropic, kainate 3P42264Rattus norvegicusPredicted (SEA)9.88685
Click to view 3D structureMetabotropic glutamate receptor 8P47743Mus musculusPredicted (SEA)5.29375
Metabotropic glutamate receptor 1 structureClick to view 3D structureMetabotropic glutamate receptor 1Q13255HumansPredicted (SEA)35.7328
Click to view 3D structureMetabotropic glutamate receptor 8P70579Rattus norvegicusPredicted (SEA)19.0731
Click to view 3D structureGlutamate receptor 1P19490Rattus norvegicusPredicted (SEA)51.7697
Click to view 3D structureGlutamate receptor ionotropic, kainate 5Q16478HumansPredicted (SEA)4.82665
Click to view 3D structureGlutamate receptor 4P48058HumansPredicted (SEA)5.29375
Click to view 3D structureMetabotropic glutamate receptor 1P23385Rattus norvegicusPredicted (SEA)43.907
Click to view 3D structureGlutamate receptor ionotropic, kainate 2P42260Rattus norvegicusPredicted (SEA)5.44945
Click to view 3D structureMetabotropic glutamate receptor 4P31423Rattus norvegicusPredicted (SEA)88.1253
Click to view 3D structureExcitatory amino acid transporter 3P51907Rattus norvegicusPredicted (SEA)0.544945
Metabotropic glutamate receptor 3 structureClick to view 3D structureMetabotropic glutamate receptor 3Q14832HumansPredicted (SEA)45.1525
Metabotropic glutamate receptor 8 structureClick to view 3D structureMetabotropic glutamate receptor 8O00222HumansPredicted (SEA)27.4029
Concentrations
Not Available
External Links
DrugBank IDDB00859
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPenicillamine
Chemspider IDNot Available
ChEBI ID7959
PubChem Compound ID5852
Kegg Compound IDC07418
YMDB IDNot Available
ECMDB IDECMDB20291
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10408968
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=13793949
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16736232
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1709917
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18570451
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19904729
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21989991
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22076732
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22151785
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22169274
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22683336
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23200399
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23342748
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23375251
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=2420897
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=7196231