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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

• Acid pKa: 8.933801
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.4786847
• LogD (pH = 7.4): -2.489615
• Log P: -2.478538
• Molar Refractivity: 61.3318 cm^3
• Polarizability: 23.156597 Å^3
• Polar Surface Area: 129.2 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.5 M, clear, colorless
• Melting Point: 222-226 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -76±2°, c = 1% in 0.1 M NaOH

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Mechanism of Action: Activates cellular functions by base pairs with Adenine HFN72-P, Cytosine HDR44-O or Uracil BTP40-U

Product Information

• Purity: ≥99%; ≥99.0% (HPLC)
• Salt Data: Free Base
• Ignition Residue: ≤0.05%; ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P); ≤0.2% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Biological Source: Prod. by microorganisms, e.g. Bacillus subtilis, E. coli, Saccharomyces cerevisiae, Fusarium spp.
• Application(s): Cardiotonic; Used to treat cardiac disorders
• Quality: crystallized
• Empirical Formula (Hill Notation): C10H12N4O5

DETAILS

Sigma Aldrich - 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.

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.

Sigma Aldrich - 57470

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

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