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[ CAS No. 6153-44-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 6153-44-2
Chemical Structure| 6153-44-2
Structure of 6153-44-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6153-44-2 ]

CAS No. :6153-44-2 MDL No. :MFCD00127824
Formula : C6H6N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :UUTDWTOZAWFKFW-UHFFFAOYSA-N
M.W : 170.12 Pubchem ID :80257
Synonyms :

Calculated chemistry of [ 6153-44-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.96
TPSA : 92.02 Ų

Pharmacokinetics

GI absorption : High
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) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.92
Log Po/w (XLOGP3) : 0.63
Log Po/w (WLOGP) : -1.15
Log Po/w (MLOGP) : -0.66
Log Po/w (SILICOS-IT) : 1.05
Consensus Log Po/w : 0.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.53
Solubility : 5.02 mg/ml ; 0.0295 mol/l
Class : Very soluble
Log S (Ali) : -2.14
Solubility : 1.24 mg/ml ; 0.00729 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.54
Solubility : 4.93 mg/ml ; 0.029 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 6153-44-2 ]

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 [ 6153-44-2 ]

* 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 [ 6153-44-2 ]
  • Downstream synthetic route of [ 6153-44-2 ]

[ 6153-44-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 67-56-1 ]
  • [ 65-86-1 ]
  • [ 6153-44-2 ]
YieldReaction ConditionsOperation in experiment
92.9% at 0 - 5℃; for 6 h; Reflux In a 500 mL three-necked flask,Add orotic acid(15.6 g, 0.10 mol),Then 300 mL of anhydrous methanol was added,Stirring down to 0 ,Maintain the temperature 0 ~ 5 drop add thionyl chloride(10.9 mL, 0.15 mol),And the temperature was raised to reflux for 6 hours.Slightly cold,Vacuum drying solvent,Add 50 mL of anhydrous methanol to lift off.150 mL of methyl t-butyl ether was added,Stirred at room temperature for 1 hour,Filter,Methyl tert-butyl ether wash.dry,To obtain 15.8 g of compound 1,Yield 92.9percent.
91 g for 30 h; Reflux At room temperature, 78 g (0.5 mol) of orotic acid B0 (containing crystal water) and 5 ml of 98percent sulfuric acid were added to 200 ml of methanol and200 ml of dimethyl carbonate solution, refluxed for 30 h, tested with TLC until the reaction was complete, the resulting solid was concentrated, washed with heat Water washed, filtered by water, and then 300ml methanol recrystallization, hot air drying, get white solid, measured melting point: mp: 246 ° C to give 83 g (0.49 mol) of the whey acid ester (B1) in a molar yield of 98percent.
Reference: [1] Patent: CN106831607, 2017, A, . Location in patent: Paragraph 0047
[2] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740
[3] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 1123 - 1126
[4] Chemische Berichte, 1930, vol. 63, p. 1000
[5] Journal of the American Chemical Society, 1947, vol. 69, p. 675
[6] Bulletin des Societes Chimiques Belges, 1953, vol. 62, p. 611,617
[7] Biochimica et Biophysica Acta, 1957, vol. 23, p. 295,303
[8] Chemical Communications, 2015, vol. 51, # 26, p. 5618 - 5621
[9] Patent: CN106938987, 2017, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052; 0053; 0054
  • 2
  • [ 80140-18-7 ]
  • [ 6153-44-2 ]
Reference: [1] Synthetic Communications, 1988, vol. 18, # 2, p. 213 - 220
  • 3
  • [ 65-86-1 ]
  • [ 6153-44-2 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 135 - 160
  • 4
  • [ 6314-14-3 ]
  • [ 6153-44-2 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1953, vol. 62, p. 611,617
  • 5
  • [ 67-56-1 ]
  • [ 3346-64-3 ]
  • [ 6153-44-2 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 135 - 160
  • 6
  • [ 6153-44-2 ]
  • [ 6299-85-0 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 1, p. 135 - 160
[2] Patent: WO2007/80382, 2007, A1, . Location in patent: Page/Page column 126-127
  • 7
  • [ 6153-44-2 ]
  • [ 6299-85-0 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 3, p. 543 - 544
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