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Chemical Structure| 16370-63-1 Chemical Structure| 16370-63-1

Structure of 16370-63-1

Chemical Structure| 16370-63-1

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Product Details of [ 16370-63-1 ]

CAS No. :16370-63-1
Formula : C5H8N4O2
M.W : 156.14
SMILES Code : COC1=NC(=NC(=N1)OC)N
MDL No. :MFCD00052765
InChI Key :KVHFZZUPCXCRIX-UHFFFAOYSA-N
Pubchem ID :27840

Safety of [ 16370-63-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 16370-63-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 37.22
TPSA ?

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

83.15 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.74
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

0.24
Log Po/w (WLOGP)?

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

-0.52
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.

-1.46
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

-0.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.05

Water Solubility

Log S (ESOL):?

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

-1.23
Solubility 9.17 mg/ml ; 0.0588 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.

-1.55
Solubility 4.44 mg/ml ; 0.0284 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

-1.16
Solubility 10.8 mg/ml ; 0.0689 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.

-7.08 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)

2.59

Application In Synthesis of [ 16370-63-1 ]

* 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 [ 16370-63-1 ]
  • Downstream synthetic route of [ 16370-63-1 ]

[ 16370-63-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 877-89-4 ]
  • [ 16370-63-1 ]
YieldReaction ConditionsOperation in experiment
86% With ammonia In water at 25 - 51℃; for 2 h; Example 3A
Preparation of 2-amino-4,6-dimethoxy-1,3,5-triazine precursor
A mixture of 10.1 g (0.059 mole) of 2,4,6-trimethoxy-1,3,5-triazine and water (100 mL) was stirred at 25° C. while 110 mL of 28percent aqueous ammonia was added.
The mixture was held at 48-51° C. for two hours before it was cooled to 25° C. and the insoluble white crystals were removed.
The product was washed with water and dried to give 7.84 g (86percent), mp 218-221° C. 1H NMR (DMSO-d): 3.81 (s, 6H); 7.38 (s, 2H).
13C NMR (DMSO-d6): 53.9, 169.0, 171.9.
References: [1] Patent: US6833454, 2004, B1, . Location in patent: Page column 6-7.
[2] Chemische Berichte, 1886, vol. 19, p. 2072.
[3] Chemische Berichte, 1870, vol. 3, p. 271.
  • 2
  • [ 108-77-0 ]
  • [ 16370-63-1 ]
YieldReaction ConditionsOperation in experiment
85.4% With ammonia; sodium methylate In methanol; water; toluene EXAMPLE 2
There is added to the atmosphere above the reaction mixture 5.1 g (0.299 moles) of ammonia gas over a 25 minute period at 20° to 40° C., to a mixture of 26.8 g (0.145 moles) of cyanuric chloride and 100 g of toluene.
The mixture is cooled to 10° C. and 25 g of methanol is added.
There is then added over a five minute period, 99.0 g of a 25percent solution of sodium methoxide to the resulting mixture causing it to reflux.
The mixture is kept under reflux for 15 minutes; there is then added 100 g of water.
A white solid is obtained after the mixture is filtered and washed with 50 g of water.
After drying at 80° C. for several hours, 20.3 g of a white solid is obtained.
Based on method of preparation, there is obtained an 85.4percent yield of 2-amino-4,6-dimethoxy-1,3,5-triazine (ADMT) based on cyanuric chloride.
References: [1] Patent: US5721364, 1998, A, .
  • 3
  • [ 74691-24-0 ]
  • [ 16370-63-1 ]
References: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 331 - 342.
  • 4
  • [ 67-56-1 ]
  • [ 933-20-0 ]
  • [ 16370-63-1 ]
References: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2986,2989.
  • 5
  • [ 30805-07-3 ]
  • [ 16370-63-1 ]
References: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 1, p. 305 - 306.
  • 6
  • [ 66030-89-5 ]
  • [ 16370-63-1 ]
References: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 331 - 342.
  • 7
  • [ 124-41-4 ]
  • [ 506-77-4 ]
  • [ 16370-63-1 ]
  • [ 877-89-4 ]
References: [1] Chemische Berichte, 1870, vol. 3, p. 271.
  • 8
  • [ 94593-91-6 ]
  • [ 16370-63-1 ]
References: [1] Journal of Agricultural and Food Chemistry, 2002, vol. 50, # 5, p. 1081 - 1088.
 

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