(2S)-2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

• ChemBase ID: 109322
• Molecular Formular: C8H16N2O4S2
• Molecular Mass: 268.35364
• Monoisotopic Mass: 268.055149
• SMILES: N[C@@H](CCSSCC[C@H](N)C(=O)O)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCSSCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6-/m0/s1
• InChIKey: ZTVZLYBCZNMWCF-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid
• Synonyms: L-HOMOCYSTINE; L-4,4′-Dithiobis(2-aminobutanoic acid); L-Homocystine; (2S)-2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid; (2S,2'S)-4,4'-Dithiobis[2-aminobutanoic Acid]; [S-(R*,R*)]-4,4'-Dithiobis[2-aminobutanoic Acid]; L-4,4'-Dithiobis[2-aminobutyric Acid]

Database IDs

• CAS Number: 626-72-2
• EC Number: 210-962-5
• MDL Number: MFCD00020391
• Beilstein Number: 1728583
• PubChem SID: 162094797; 24895724; 24877552
• PubChem CID: 439579

CALCULATED PROPERTIES

• Acid pKa: 1.8009555
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.320504
• LogD (pH = 7.4): -5.326616
• Log P: -5.320484
• Molar Refractivity: 64.3818 cm^3
• Polarizability: 25.817242 Å^3
• Polar Surface Area: 126.64 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid
• Apperance: White Solid
• Melting Point: 252-257°C (dec.); 281-284 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +77±3°, c = 1% in 1 M HCl
• Hydrophobicity(logP): -3.871

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥98.0% (NT); null%
• Grade: purum
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C8H16N2O4S2

DETAILS

MP Biomedicals - 05210615

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - H591360

Increased levels lead to hyperhomocysteinemia; a cardiovascular risk factor in prediction of coronary heart disease as well as being associated with congenital birth defects, pregnancy complications and cancer.

REFERENCES

• Geisel, J. et al.: Clin. Chem. Lab. Med., 41, 1513 (2003)
• Geisel, J. et al.: Clin. Chem. Lab. Med., 41, 1513 (2003)