CAS 58-63-9|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)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one|(-)-Inosine|Inosine|O...

General Information

Structure

Molecular Formula

C₁₀H₁₂N₄O₅

Molecular Mass

268.22608

Exact Mass

268.0807695

Charge

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

Canonic Smiles

OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc[nH]c2=O

Isomeric Smiles

n1(c2c(nc1)c(=O)[nH]cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O

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

Polarizability

23.156597

Polar Surface Area

129.2

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

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)-oneInosine(-)-InosineOxiamineTrophicardylInosieHypoxanthosineCarnineHypoxanthine ribosideInosineHypoxanthine 9-β-D-ribofuranoside

IUPAC name

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

Names and Identifiers

Registration numbers

EC Number

Beilstein Number

CAS Number

PubChem SID

MDL Number

PubChem CID

Registration numbers

Properties

Physical Property

222-226 °C (dec.)(lit.)

H2O: soluble0.5 M, clear, colorless

[α]20/D -76±2°, c = 1% in 0.1 M NaOH

Safety Information

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

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Pharmacology Properties

Activates cellular functions by base pairs with Adenine HFN72-P, Cytosine HDR44-O or Uracil BTP40-U

Others

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

I1024

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.

I4125

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.

57470

Molecule Details

References

PubChem Literature

From Data Sources

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 712B, (ir)

• Gulland, J.M. et al., J.C.S., 1936, 765, (struct)

• Hawkes, G.E. et al., J.C.S. Perkin 2, 1977, 1268, (N-15 nmr)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 548; 1379

• 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

• Japan. Pat., 1968, 68 13 215; CA, 70, 47808, (synth, isopropylidene)

• Westhof, E. et al., Z. Naturforsch., C, 1975, 30, 131, (pmr)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 215C, (nmr)

• Chenon, M.T. et al., J.A.C.S., 1975, 97, 4627, (cmr)

• Yamazaki, A. et al., J. Het. Chem., 1978, 15, 353, (rev, synth)

• Munns, A.R.I. et al., Acta Cryst. B, 1970, 26, 1114, (cryst struct)

• Hall, R.H., Biochem. Biophys. Res. Commun., 1963, 13, 394, (isol, deriv)

• Aviado, D.M., J. Pharmacol., 1983, 14, 47, (rev, pharmacol)

• De Simone, C. et al., Int. J. Immunopharmacol., 1991, 13, 19, (rev, Inosine pranobex)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, IDE000

• Kinichi, I. et al., Chem. Pharm. Bull., 1966, 14, 1377, (synth)

• Ger. Pat., 1972, 2038262; CA, 76, 99993e, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

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

IUPAC name

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

Registration numbers

EC Number

Beilstein Number

CAS Number

PubChem SID