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Structure of 6270-46-8

Chemical Structure| 6270-46-8

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Product Details of [ 6270-46-8 ]

CAS No. :6270-46-8
Formula : C5H7N3O2
M.W : 141.13
SMILES Code : CC1=C(N)C(O)=NC(O)=N1
MDL No. :MFCD00053572
InChI Key :FNSSATCDUXTALE-UHFFFAOYSA-N
Pubchem ID :80453

Safety of [ 6270-46-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 6270-46-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 0
Num. H-bond acceptors 4.0
Num. H-bond donors 3.0
Molar Refractivity 35.45
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

92.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.78
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.12
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.21
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-1.05
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.28
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.18

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.08
Solubility 11.6 mg/ml ; 0.0825 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.36
Solubility 6.1 mg/ml ; 0.0432 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.51
Solubility 44.1 mg/ml ; 0.313 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.25 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.95

Application In Synthesis of [ 6270-46-8 ]

* 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.

  • Downstream synthetic route of [ 6270-46-8 ]

[ 6270-46-8 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 75-21-8 ]
  • [ 6270-46-8 ]
  • [ 31492-83-8 ]
  • 2
  • [ 64-18-6 ]
  • [ 6270-46-8 ]
  • [ 7357-42-8 ]
  • 3
  • [ 79-36-7 ]
  • [ 6270-46-8 ]
  • [ 98550-99-3 ]
  • 4
  • [ 6270-46-8 ]
  • [ 61066-33-9 ]
  • 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylimino)-barbituric acid [ No CAS ]
  • 5
  • [ 6270-46-8 ]
  • [ 594-03-6 ]
  • <i>N</i>-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-thioacetamide [ No CAS ]
  • 6
  • [ 6270-46-8 ]
  • [ 4472-10-0 ]
  • <i>N</i>-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-thioformamide [ No CAS ]
  • 7
  • [ 6270-46-8 ]
  • [ 541-41-3 ]
  • [ 98594-84-4 ]
  • 8
  • [ 6270-46-8 ]
  • [ 79-11-8 ]
  • [ 27870-38-8 ]
  • 9
  • [ 6270-46-8 ]
  • [ 79-04-9 ]
  • [ 27870-38-8 ]
  • 10
  • [ 6270-46-8 ]
  • [ 598-72-1 ]
  • 2-bromo-propionic acid-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide) [ No CAS ]
  • 11
  • [ 6270-46-8 ]
  • [ 407-25-0 ]
  • [ 1513-51-5 ]
  • 12
  • [ 6270-46-8 ]
  • [ 121-60-8 ]
  • <i>N</i>-acetyl-sulfanilic acid-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide) [ No CAS ]
  • 13
  • [ 6270-46-8 ]
  • [ 91114-11-3 ]
  • 14
  • [ 16632-21-6 ]
  • [ 6270-46-8 ]
  • 15
  • [ 76982-09-7 ]
  • [ 6270-46-8 ]
  • 16
  • [ 6270-46-8 ]
  • [ 100-01-6 ]
  • 5-oxo-4,5-dihydro-[1,2,3]oxadiazolo[5,4-<i>d</i>]pyrimidine-7-carbaldehyde (4-nitro-phenyl)-hydrazone [ No CAS ]
  • 19
  • [ 7647-01-0 ]
  • [ 412307-93-8 ]
  • [ 6270-46-8 ]
  • 20
  • 5-bromo-4-methyl-uracil [ No CAS ]
  • [ 6270-46-8 ]
  • 21
  • 5-nitro-4-methyl-uracil [ No CAS ]
  • [ 6270-46-8 ]
  • 22
  • [ 6270-46-8 ]
  • potassium permanganate [ No CAS ]
  • acetylcarbamoyl-oxalamic acid [ No CAS ]
  • 23
  • [ 6270-46-8 ]
  • potassium permanganate [ No CAS ]
  • [ 591-07-1 ]
  • [ 585-05-7 ]
  • 24
  • [ 6270-46-8 ]
  • 4-methyl-1,5-dihydro-pyrimido[4,5-<i>b</i>][1,4]oxazine-2,6-dione [ No CAS ]
  • 26
  • [ 6270-46-8 ]
  • sulfanilic acid-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylamide) [ No CAS ]
  • 27
  • [ 15663-27-1 ]
  • [ 6270-46-8 ]
  • [ 104626-67-7 ]
  • 28
  • [ 6270-46-8 ]
  • [ 1220690-65-2 ]
  • 6-hydroxy-5-hydroxyimino-6-methyldihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • [ 861542-63-4 ]
YieldReaction ConditionsOperation in experiment
18%; 18%; 25% With 1,4-dioxane; 2,2'-azobis(isobutyronitrile); at 60.0℃; for 3.75h; A glass reactor was charged with 1,4-dioxane (127 ml) containing <strong>[6270-46-8]5-amino-6-methyluracil</strong> (1) (50.0 mg, 0.35 mmol), and a solution of AIBN (248.0 mg, 1.50 mmol) in 1,4-dioxane (12.6 ml). The oxidation was performed at 60 C temperature for 225 min with constant stirring and bubbling of air until complete consumption of compound 1, determined photometrically at 290 nm wavelength. 1,4-Dioxane was removed from the reaction mixture under vacuum, the residue was washed with hot benzene (5×3 ml) to remove AIBN and the products of 1,4-dioxane oxidation. A mixture of oxidation products was obtained (44.2 mg) and separated by HPLC. 5,5,6-Trihydroxy-6-methyldihydropyrimidine-2,4(1H,3H)-dione (2). Yield 25%.* White crystals, mp 122-123 C.17,21 UV spectrum, lambdamax, nm: 203. 13C NMR spectrum, delta, ppm: 19.9 (CH3); 83.2 (C-6); 88.4 (C-5); 151.8 (C-2); 172.9 (C-4). Mass spectrum, m/z (Irel, %): 215 [M+K]+ (0.4). 6-Hydroxy-6-methyldihydropyrimidine-2,4,5(3H)-trione (3). Yield 18%. White crystals.17,21 UV spectrum, lambdamax, nm: 210. 13C NMR spectrum, delta, ppm: 25.7 (CH3); 86.9 (C-6); 157.0 (C-2); 174.7 (C-4); 207.0 (C-5). Mass spectrum, m/z (Irel, %): 197 [M+K]+ (1). 6-Hydroxy-5-hydroxyimino-6-methyldihydropyrimidine-2,4(1H,3H)-dione (4). Yield 18%, pale-yellow crystalline powder, mp 136 C (decomp.). UV spectrum, lambdamax, nm: 208, 274. 1H NMR spectrum, delta, ppm: 2.16 (3, s, CH3); 5.43 (1, br. s, 1-NH); 8.46 (2, br. s, 2OH). 13C NMR spectrum, delta, ppm: 20.8 (CH3); 94.7 (C-6); 152.0 (C-4); 153.9 (C-5); 160.7 (C-2). Mass spectrum, m/z (Irel,%): 230 [M+K+H2O]+ (61).
 

Historical Records

Technical Information

Categories

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