D-Penicillamine (CHEM017477)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:23:23 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017477
Identification
Common NameD-Penicillamine
ClassSmall Molecule
DescriptionPenicillamine is a pharmaceutical of the chelator class. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine). It is an α-amino acid metabolite of penicillin, although it has no antibiotic properties.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr5-1930000000-6ee8522d7087601d49e6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9520000000-1ac6006c4f882c72292bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9640000000-736237ccaaa4ef171daaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-ca3b0f005a0900197cf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufr-7900000000-bad3a6cc0c32a1b4493cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-9f0f7aaf661aaceff17cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0900000000-3e88f7f9375f31828829Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-3900000000-2f3ec3dbefe757ef98d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9100000000-455730a935564d9415d5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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