(4R)-2-amino-4,5-dihydro-1,3-thiazole-4-carboxylic acid

• ChemBase ID: 160511
• Molecular Formular: C4H6N2O2S
• Molecular Mass: 146.16764
• Monoisotopic Mass: 146.01499844
• SMILES: S1C[C@H](N=C1N)C(=O)O
• Canonical SMILES: NC1=N[C@@H](CS1)C(=O)O
• InChI: InChI=1S/C4H6N2O2S/c5-4-6-2(1-9-4)3(7)8/h2H,1H2,(H2,5,6)(H,7,8)/t2-/m0/s1
• InChIKey: VHPXSBIFWDAFMB-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-2-amino-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• IUPAC Traditional name: (4R)-2-amino-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• Synonyms: (4R)-2-Amino-4,5-dihydro-4-thiazolecarboxylic Acid; (R)-2-Amino-4,5-dihydro-4-thiazolecarboxylic Acid; L-2-Imino-4-thiazolidinecarboxylic Acid; L-2-Aminothiazoline-4-carboxylic Acid; (4S)-2-Amino-4,5-dihydro-4-thiazolecarboxylic Acid; (S)-2-Amino-4,5-dihydro-4-thiazolecarboxylic Acid; D-2-Amino-2-thiazolin-4-carboxylic Acid; D-2-Aminothiazoline-4-carboxylic Acid

Database IDs

• CAS Number: 69222-97-5; 16899-18-6
• PubChem SID: 162254646
• PubChem CID: 7272538

CALCULATED PROPERTIES

• Acid pKa: 2.2805068
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.7497303
• LogD (pH = 7.4): -1.8184185
• Log P: -1.7495472
• Molar Refractivity: 33.5252 cm^3
• Polarizability: 12.960123 Å^3
• Polar Surface Area: 75.68 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A630500

A thiozole derivative that is converted to D-cysteine by the enzyme 2-amino-Δ2-thiazoline-4-carboxylic acid hydrolase (ATCase) upon induction by S-compounds in certain bacteria.

Toronto Research Chemicals - A630505

A thiozole derivative that is converted to L-cysteine by the enzyme 2-amino-Δ2-thiazoline-4-carboxylic acid hydrolase (ATCase) upon induction by S-compounds in certain bacteria.

REFERENCES

• Tamura, Y. et al.: J. Gen. Appl. Microbiol., 47, 193 (2001)
• Tamura, Y. et al.: J. Gen. Appl. Microbiol., 47, 193 (2001)
• Shiba, T. et al.: J. Gen. Appl. Microbiol., 68, 2179 (2001)