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58-63-9 molecular structure
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9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

ChemBase ID: 119255
Molecular Formular: C10H12N4O5
Molecular Mass: 268.22608
Monoisotopic Mass: 268.0807695
SMILES and InChIs

SMILES:
n1(c2c(nc1)c(=O)[nH]cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
Canonical SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc[nH]c2=O
InChI:
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChIKey:
UGQMRVRMYYASKQ-KQYNXXCUSA-N

Cite this record

CBID:119255 http://www.chembase.cn/molecule-119255.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
IUPAC Traditional name
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Synonyms
9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
Inosine
(-)-Inosine
Hypoxanthine 9-β-D-ribofuranoside
Inosine
Hypoxanthine riboside
Hypoxanthosine
Inosie
Oxiamine
Trophicardyl
Carnine
CAS Number
58-63-9
EC Number
200-390-4
MDL Number
MFCD00066770
Beilstein Number
624896
PubChem SID
162102976
24896051
PubChem CID
6021

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.933801  H Acceptors
H Donor LogD (pH = 5.5) -2.4786847 
LogD (pH = 7.4) -2.489615  Log P -2.478538 
Molar Refractivity 61.3318 cm3 Polarizability 23.156597 Å3
Polar Surface Area 129.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: soluble0.5 M, clear, colorless expand Show data source
Melting Point
222-226 °C (dec.)(lit.) expand Show data source
Optical Rotation
[α]20/D -76±2°, c = 1% in 0.1 M NaOH expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
Others expand Show data source
Mechanism of Action
Activates cellular functions by base pairs with Adenine HFN72-P, Cytosine HDR44-O or Uracil BTP40-U expand Show data source
Purity
≥99% expand Show data source
≥99.0% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Ignition Residue
≤0.05% expand Show data source
≤0.1% expand Show data source
Impurities
≤0.0005% Phosphorus (P) expand Show data source
≤0.2% Insoluble matter expand Show data source
Cation Traces
Al: ≤0.0005% expand Show data source
Ca: ≤0.0005% expand Show data source
Cu: ≤0.0005% expand Show data source
Fe: ≤0.0005% expand Show data source
K: ≤0.005% expand Show data source
Mg: ≤0.0005% expand Show data source
Na: ≤0.005% expand Show data source
NH4+: ≤0.05% expand Show data source
Pb: ≤0.001% expand Show data source
Zn: ≤0.0005% expand Show data source
Antion Traces
chloride (Cl-): ≤0.05% expand Show data source
sulfate (SO42-): ≤0.05% expand Show data source
Biological Source
Prod. by microorganisms, e.g. Bacillus subtilis, E. coli, Saccharomyces cerevisiae, Fusarium spp. expand Show data source
Application(s)
Cardiotonic expand Show data source
Used to treat cardiac disorders expand Show data source
Quality
crystallized expand Show data source
Empirical Formula (Hill Notation)
C10H12N4O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - I4125 external link
包装
1, 5, 10, 25, 100 g in poly bottle
Biochem/physiol Actions
Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing.
Sigma Aldrich - I1024 external link
Biochem/physiol Actions
Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing.
Sigma Aldrich - 57470 external link
Biochem/physiol Actions
Inosine is a potent stimulator of nerve growth factor (NGF) induced neurite outgrowth. The elevated levels of inosine in brain following injury are associated with the increased expression proteins related to axonal regeneration and growth. Mice given inosine demonstrated enhanced recovery of fine motor control following ischemic brain damage. Inosine may be used in studies of the process A-to-I RNA editing.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 215C, (nmr)
  • • Gulland, J.M. et al., J.C.S., 1936, 765, (struct)
  • • Hall, R.H., Biochem. Biophys. Res. Commun., 1963, 13, 394, (isol, deriv)
  • • Kinichi, I. et al., Chem. Pharm. Bull., 1966, 14, 1377, (synth)
  • • Japan. Pat., 1968, 68 13 215; CA, 70, 47808, (synth, isopropylidene)
  • • Munns, A.R.I. et al., Acta Cryst. B, 1970, 26, 1114, (cryst struct)
  • • Ger. Pat., 1972, 2038262; CA, 76, 99993e, (synth)
  • • Chenon, M.T. et al., J.A.C.S., 1975, 97, 4627, (cmr)
  • • Westhof, E. et al., Z. Naturforsch., C, 1975, 30, 131, (pmr)
  • • Hawkes, G.E. et al., J.C.S. Perkin 2, 1977, 1268, (N-15 nmr)
  • • Yamazaki, A. et al., J. Het. Chem., 1978, 15, 353, (rev, synth)
  • • Aviado, D.M., J. Pharmacol., 1983, 14, 47, (rev, pharmacol)
  • • Campoli-Richards, D.M. et al., Drugs, 1986, 32, 383, (rev, Inosine pranobex)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1551
  • • De Simone, C. et al., Int. J. Immunopharmacol., 1991, 13, 19, (rev, Inosine pranobex)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 548; 1379
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IDE000
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PATENTS

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