(2S)-2-amino-4-sulfanylbutanoic acid

• ChemBase ID: 4005
• Molecular Formular: C4H9NO2S
• Molecular Mass: 135.18476
• Monoisotopic Mass: 135.03539953
• SMILES: N[C@@H](CCS)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCS
• InChI: InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1
• InChIKey: FFFHZYDWPBMWHY-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-sulfanylbutanoic acid
• IUPAC Traditional name: L-homocysteine; C4H9NO2S
• Synonyms: (S)-2-Amino-4-mercaptobutyric acid; L-Homocysteine; 2-Amino-4-Mercapto-Butyric Acid

Database IDs

• CAS Number: 6027-13-0
• EC Number: 227-891-0
• MDL Number: MFCD00151320
• PubChem SID: 46507349; 160967440
• PubChem CID: 91552

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4585538
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.5765834
• LogD (pH = 7.4): -2.580165
• Log P: -2.5764673
• Molar Refractivity: 32.935 cm^3
• Polarizability: 13.237369 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.29
• LOG S: -0.96
• Solubility (Water): 1.48e+01 g/l

PROPERTIES

Physical Property

• Optical Rotation: [α]/D 25.5±1.5°, c = 1 in 1 M HCl

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (NT)
• Linear Formula: HSCH2CH2CH(NH2)COOH

DETAILS

DrugBank - DB04422

• Drug Groups: experimental
• Description: A thiol-containing amino acid formed by a demethylation of METHIONINE. [PubChem]

Sigma Aldrich - 69453

Biochem/physiol Actions
Elevated homocysteine levels in plasma and tissue are associated with brain atrophy in Alzheimer′s disease as well as in healthy eldery subjects. Increased homocysteine is due to deficiencies in vitamin B status, specifically folate, B6 and B12 vitamins, which act as cofactors for enzymes involved in homocysteine metabolism.1