(2S)-2-amino-3-{[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl}-3-methylbutanoic acid

• ChemBase ID: 146563
• Molecular Formular: C10H20N2O4S2
• Molecular Mass: 296.4068
• Monoisotopic Mass: 296.08644913
• SMILES: CC(C)([C@H](C(=O)O)N)SSC(C)(C)[C@H](C(=O)O)N
• Canonical SMILES: N[C@H](C(SSC([C@H](C(=O)O)N)(C)C)(C)C)C(=O)O
• InChI: InChI=1S/C10H20N2O4S2/c1-9(2,5(11)7(13)14)17-18-10(3,4)6(12)8(15)16/h5-6H,11-12H2,1-4H3,(H,13,14)(H,15,16)/t5-,6-/m0/s1
• InChIKey: POYPKGFSZHXASD-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[(1S)-1-amino-1-carboxy-2-methylpropan-2-yl]disulfanyl}-3-methylbutanoic acid
• IUPAC Traditional name: D-penicillamine disulfide
• Synonyms: 3,3′-Dithiobis-D-valine; NSC 87505; 3,3′-Dithiobis(2-amino-3-methylbutanoic acid); 3,3′-Dithiobis(2-amino-3-methylbutyric acid); S,S′-Bi(D-penicillamine); D-Penicillamine disulfide; 3,3′-二硫代双(2-氨基-3-甲基丁酸); S,S′-二(D-青霉胺); 二硫青霉胺; D-青霉胺二硫化物

Database IDs

• CAS Number: 20902-45-8
• EC Number: 244-107-2
• MDL Number: MFCD00004264
• Beilstein Number: 4461521
• PubChem SID: 24898153; 24886988; 162240757
• PubChem CID: 9882671

CALCULATED PROPERTIES

• Acid pKa: 1.8552737
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.1486697
• LogD (pH = 7.4): -4.1611524
• Log P: -4.148753
• Molar Refractivity: 72.6538 cm^3
• Polarizability: 29.47467 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 204 °C (dec.)(lit.); 204-205 °C(lit.)
• Optical Rotation: [α]20/D +28±1°, c = 1.5% in 1 M HCl; [α]25/D -75°, c = 1 in 1 M NaOH

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (NT); 97%
• Grade: purum
• Linear Formula: [-SC(CH3)2CH(NH2)CO2H]2
• Empirical Formula (Hill Notation): C10H20N2O4S2

DETAILS

Sigma Aldrich - P1101

Packaging
1 g in glass bottle
Application
Used in pharmacological studies of:
• Molecules dermatomyositis activity1
• Antimelanoma activity of apoptogenic carbonyl scavengers2

Sigma Aldrich - 76422

Other Notes
Thiol reagent1