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[ CAS No. 58-63-9 ] {[proInfo.proName]}

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Chemical Structure| 58-63-9
Chemical Structure| 58-63-9
Structure of 58-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 58-63-9 ]

CAS No. :58-63-9 MDL No. :MFCD00066770
Formula : C10H12N4O5 Boiling Point : -
Linear Structure Formula :- InChI Key :UGQMRVRMYYASKQ-KQYNXXCUSA-N
M.W : 268.23 Pubchem ID :135398641
Synonyms :
9-β-D-Ribofuranosylhypoxanthine;NSC 20262;INO 495

Calculated chemistry of [ 58-63-9 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 4.0
Molar Refractivity : 61.1
TPSA : 133.49 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.38
Log Po/w (XLOGP3) : -2.1
Log Po/w (WLOGP) : -2.59
Log Po/w (MLOGP) : -1.85
Log Po/w (SILICOS-IT) : -1.51
Consensus Log Po/w : -1.69

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.4
Solubility : 107.0 mg/ml ; 0.399 mol/l
Class : Very soluble
Log S (Ali) : -0.18
Solubility : 179.0 mg/ml ; 0.668 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.14
Solubility : 373.0 mg/ml ; 1.39 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.77

Safety of [ 58-63-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58-63-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 58-63-9 ]
  • Downstream synthetic route of [ 58-63-9 ]

[ 58-63-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 58-63-9 ]
  • [ 77-76-9 ]
  • [ 2140-11-6 ]
YieldReaction ConditionsOperation in experiment
80% With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 24 h; Inert atmosphere To a solution of Inosine (0.998 g, 3.72 mmoli) in DMF (30 ml) were added 2,2-Dimethxypropane(1.8 mL, 14.59 mmoli) and p-Toluensulfonic acid monohydrate (0.038g, 0.372 mmoli). The reaction mixture was stirred under Ar for 24 h. After the evaporation of DMF, the reaction was basified with a solution of NH3 3percent and the evaporated to dryness. The residue obtained was purified by chromatography over silica gel (eluent: CH2Cl2/MeOH 95/5 v/v) to afford desiderated compound 22 as white foam (yield 80percent). 1H-NMR (200MHz, DMSO-d6) d: 1.34,1.50 (6H, s, (CH3)2C), 3.6 (2H, t, CH2-5'), 4.37 (1H, m, H-4'), 4.94 (1H, m, H-3'), 5.18 (1H, t, OH 5'), 5.37 (1H, dd, J=3.7, H-2',), 6.12 (1H, d, J=2.4, H-1'), 8.05 (1H, s, H-2), 8.32 (1H, s, H-8), 12.44 (1H, br s, NH-3). ESI MS: m/z 309.1 Da [M+H]+, C13H16N4O5 Mol. Wt. 308.29.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 202 - 209
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2087 - 2103
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5349 - 5370
[4] Heterocycles, 2013, vol. 87, # 11, p. 2369 - 2384
[5] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1439 - 1442
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
  • 2
  • [ 58-63-9 ]
  • [ 67-64-1 ]
  • [ 2140-11-6 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 27, p. 5228 - 5239
[2] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 881 - 885
[3] Chinese Chemical Letters, 2014, vol. 25, # 12, p. 1583 - 1585
  • 3
  • [ 58-63-9 ]
  • [ 149-73-5 ]
  • [ 2140-11-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 49, p. 6463 - 6465
  • 4
  • [ 99790-49-5 ]
  • [ 58-63-9 ]
Reference: [1] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165
[2] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165
  • 5
  • [ 118-00-3 ]
  • [ 58-63-9 ]
Reference: [1] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165
  • 6
  • [ 146469-96-7 ]
  • [ 99790-49-5 ]
  • [ 58-63-9 ]
Reference: [1] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165
  • 7
  • [ 58-96-8 ]
  • [ 58-63-9 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13401 - 13419
  • 8
  • [ 58-61-7 ]
  • [ 58-63-9 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 3, p. 613 - 624
[2] Journal of the American Chemical Society, 2013, vol. 135, # 9, p. 3465 - 3473
[3] ChemPlusChem, 2013, vol. 78, # 2, p. 157 - 165
  • 9
  • [ 68-94-0 ]
  • [ 58-96-8 ]
  • [ 58-63-9 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13401 - 13419
  • 10
  • [ 131-99-7 ]
  • [ 58-63-9 ]
Reference: [1] Food Chemistry, 2012, vol. 134, # 2, p. 948 - 956
  • 11
  • [ 68-94-0 ]
  • [ 58-63-9 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 38, p. 13401 - 13419
  • 12
  • [ 108-24-7 ]
  • [ 58-63-9 ]
  • [ 3181-38-2 ]
YieldReaction ConditionsOperation in experiment
82% With dmap; triethylamine In acetonitrile at 20℃; for 1 h; To a suspension of inosine (1 Og, 37. 3mmol) and catalytic DMAP in MeCN (60mL) was added Et3N (20mL, 143mmol) and acetic anhydride (12.5mL) and the resulting solution was stirred for 1h at ambient temperature before the addition of MeOH (5mL). After stirring for 5mins, the solution was concentrated in vacuo to yield a white solid which was washed with isopropyl alcohol to afford triacetoxy inosine (12. 1g, 82percent).
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[2] Synthesis, 2003, # 17, p. 2639 - 2642
[3] Journal of the American Chemical Society, 1997, vol. 119, # 32, p. 7423 - 7433
[4] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[5] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11634 - 11643
[6] Synlett, 2006, # 20, p. 3474 - 3478
[7] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 5, p. 859 - 866
[8] Journal of applied chemistry of the USSR, 1984, vol. 57, # 9 pt 2, p. 1991 - 1992
[9] Patent: WO2005/54269, 2005, A1, . Location in patent: Page/Page column 14
[10] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[12] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[13] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[14] Patent: EP2407474, 2012, A1, . Location in patent: Page/Page column 5
[15] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
  • 13
  • [ 2466-76-4 ]
  • [ 58-63-9 ]
  • [ 3181-38-2 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydroxide In water at 20℃; for 4 h; General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.
Reference: [1] Synlett, 2017, vol. 28, # 1, p. 78 - 83
  • 14
  • [ 4551-95-5 ]
  • [ 58-63-9 ]
  • [ 4338-48-1 ]
  • [ 68-94-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 11, p. 2520 - 2528
  • 15
  • [ 108-24-7 ]
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
  • 16
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[2] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[3] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[5] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[7] Patent: EP2407474, 2012, A1,
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
  • 17
  • [ 58-63-9 ]
  • [ 5987-73-5 ]
Reference: [1] British Journal of Pharmacology, 2017, vol. 174, # 14, p. 2287 - 2301
[2] Patent: WO2005/84653, 2005, A2,
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