2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• ChemBase ID: 179693
• Molecular Formular: C13H19NO9
• Molecular Mass: 333.29126
• Monoisotopic Mass: 333.10598119
• SMILES: C(C(C(=O)O)O)(C(=O)O)O.c1c(c(ccc1[C@@H](O)CNC)O)O
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.CNC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)
• InChIKey: YLXIPWWIOISBDD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC Traditional name: 2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• Synonyms: Adrenaline; Epitrate; Epinephrine Bitartrate

Database IDs

• CAS Number: 51-42-3
• PubChem SID: 164235603
• PubChem CID: 6852374

CALCULATED PROPERTIES

• Acid pKa: 9.69426
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.8488538
• LogD (pH = 7.4): -1.6309718
• Log P: -0.42952928
• Molar Refractivity: 49.2303 cm^3
• Polarizability: 19.213377 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Neurotransmitter

Product Information

• Salt Data: Bitartrate
• Application(s): Ophthalmic adrenergic agent

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 625B, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 1296A, (ir)
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• Ciocca, B., Boll. Chim. Farm., 1934, 73, 241; CA, 28, 4398, (synth)
• Pratesi, P. et al., J.C.S., 1959, 4062, (abs config)
• Payne, K.R., Ind. Chem., 1961, 37, 523, (manuf, bibl)
• Thies, H. et al., Arch. Pharm. (Weinheim, Ger.), 1962, 295, 194, (uv)
• Jerman, L. et al., Anal. Chim. Acta, 1966, 36, 240, (use)
• Carlstrm, D., Acta Cryst. B, 1973, 29, 161, (cryst struct)
• Hawkins, C.J. et al., Aust. J. Chem., 1973, 26, 2553, (resoln)
• Samokish, I.I. et al., CA, 1975, 84, 102283, (isol, deriv)
• Nagatsu, T., Method. Chim., 1977, 11, 194, (rev)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AES000; AES250; AES500; AES625; EBB500; MJV000; VGP000