2,3-dihydroxybutanedioic acid; 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

• ChemBase ID: 179718
• Molecular Formular: C12H17NO9
• Molecular Mass: 319.26468
• Monoisotopic Mass: 319.09033113
• SMILES: C(C(C(=O)O)O)(C(=O)O)O.c1c(c(ccc1[C@H](O)CN)O)O
• Canonical SMILES: OC(=O)C(C(C(=O)O)O)O.NC[C@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C8H11NO3.C4H6O6/c9-4-8(12)5-1-2-6(10)7(11)3-5;5-1(3(7)8)2(6)4(9)10/h1-3,8,10-12H,4,9H2;1-2,5-6H,(H,7,8)(H,9,10)
• InChIKey: WNPNNLQNNJQYFA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydroxybutanedioic acid; 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• IUPAC Traditional name: 2,3-dihydroxybutanedioic acid; 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• Synonyms: Arterenol; Norepinephrine; Levophed; Noradrenaline Bitartrate

Database IDs

• CAS Number: 51-40-1
• PubChem SID: 164235628
• PubChem CID: 18530234

CALCULATED PROPERTIES

• Acid pKa: 9.500885
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.0654356
• LogD (pH = 7.4): -1.8244592
• Log P: -0.6835134
• Molar Refractivity: 44.4557 cm^3
• Polarizability: 17.37873 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: alpha, beta 1 Adrenoceptor agonist; Bronchodilator; Sympathomimetic

Product Information

• Salt Data: Bitartrate
• Application(s): Bronchodilator; Sympathomimetic; Vasopressor

REFERENCES

• Biel, J.H. et al., J.A.C.S., 1954, 76, 3149-3153, (synth, pharmacol)
• Waalkes, T.P. et al., Science (Washington, D.C.), 1958, 127, 648-650, (isol)
• Udenfriend, S. et al., Arch. Biochem. Biophys., 1959, 85, 487-490, (detn, occur)
• Pratesi, P. et al., J.C.S., 1959, 4062-4065, (abs config)
• Levy, B. et al., Drill's Pharmacol. Med., 4th edn., McGraw-Hill, New York, 1971, 627, (rev, pharmacol)
• Applewhite, P.B., Phytochemistry, 1973, 12, 191-192, (occur)
• Donike, M., Chromatographia, 1974, 7, 651-654, (ms)
• Andersen, A.M., Acta Chem. Scand., Ser. B, 1975, 29, 871-876, (cryst struct)
• Rajan, K.S. et al., Bioinorg. Chem., 1976, 6, 93-117, (uv)
• Smith, T.A., Phytochemistry, 1977, 16, 9-18, (occur, bibl)
• Wilson, T.D. et al., Anal. Profiles Drug Subst., 1982, 11, 555, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1249
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ARL500; NNP050; NNO500; NNO699; ARL750