(3S)-3-amino-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-one hydrochloride

• ChemBase ID: 160024
• Molecular Formular: C9H10ClNO4
• Molecular Mass: 231.633
• Monoisotopic Mass: 231.02983549
• SMILES: c1c(c(cc2c1C[C@@H](C(=O)O2)N)O)O.Cl
• Canonical SMILES: N[C@H]1Cc2cc(O)c(cc2OC1=O)O.Cl
• InChI: InChI=1S/C9H9NO4.ClH/c10-5-1-4-2-6(11)7(12)3-8(4)14-9(5)13;/h2-3,5,11-12H,1,10H2;1H/t5-;/m0./s1
• InChIKey: YVQRYXRJOZIZND-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-amino-6,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-one hydrochloride
• IUPAC Traditional name: (3S)-3-amino-6,7-dihydroxy-3,4-dihydro-1-benzopyran-2-one hydrochloride
• Synonyms: (S)-3-Amino-3,4-dihydro-6,7-dihydroxy-2H-1-benzopyran-2-one Hydrochloride; (S)-3-Amino-6,7-dihydroxyhydrocoumarin Hydrochloride

Database IDs

• CAS Number: 30033-29-5
• PubChem SID: 162254159
• PubChem CID: 71313202

CALCULATED PROPERTIES

• Acid pKa: 8.930222
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.0759234
• LogD (pH = 7.4): 0.17693372
• Log P: 0.3010911
• Molar Refractivity: 47.5668 cm^3
• Polarizability: 18.670801 Å^3
• Polar Surface Area: 92.78 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A604955

A couramin derivative that is precursor in the preparation of L-DOPA analogues.

REFERENCES

• Kaiser, A. et al.: Helv. Chim. Acta, 53, 1708 (1970)