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51-42-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:179693 http://www.chembase.cn/molecule-179693.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
51-42-3
PubChem SID
164235603
PubChem CID
6852374

DATA SOURCES

DATA SOURCES

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Data Source Data ID
PubChem 6852374 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.69426  H Acceptors
H Donor LogD (pH = 5.5) -2.8488538 
LogD (pH = 7.4) -1.6309718  Log P -0.42952928 
Molar Refractivity 49.2303 cm3 Polarizability 19.213377 Å3
Polar Surface Area 72.72 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Pharmacology Properties Product Information Bioassay(PubChem)
Mechanism of Action
Neurotransmitter expand Show data source
Salt Data
Bitartrate expand Show data source
Application(s)
Ophthalmic adrenergic agent expand Show data source

DETAILS

DETAILS

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
  • • Abderhalden, E. et al., Ber., 1904, 37, 2022, (isol)
  • • 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)
  • • Szulczewski, D. et al., Anal. Profiles Drug Subst., 1978, 7, 193, (rev)
  • • Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 9, 241, (rev)
  • • Weisser, U., Med. Welt, 1980, 31, 40, (synth)
  • • Lai, A. et al., J.C.S. Faraday 2, 1981, 77, 227, (cmr)
  • • Endress, R. et al., J. Plant Physiol., 1984, 115, 291; CA, 101, 127016u, (occur)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1288, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1238
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AES000; AES250; AES500; AES625; EBB500; MJV000; VGP000
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PATENTS

PATENTS

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INTERNET

INTERNET

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