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Structure of 39745-39-6

Chemical Structure| 39745-39-6

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Product Details of [ 39745-39-6 ]

CAS No. :39745-39-6
Formula : C6H6N2O3
M.W : 154.12
SMILES Code : CC1=CC=C(C(O)=N1)[N+]([O-])=O
MDL No. :MFCD03001414
InChI Key :YVYDGIGILRUPED-UHFFFAOYSA-N
Pubchem ID :543029

Safety of [ 39745-39-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 39745-39-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 40.05
TPSA ?

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

78.94 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.1
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

1.61
Log Po/w (WLOGP)?

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

1.0
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.

-0.56
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

-0.81
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.47

Water Solubility

Log S (ESOL):?

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

-2.15
Solubility 1.1 mg/ml ; 0.00712 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.88
Solubility 0.203 mg/ml ; 0.00132 mol/l
Class?

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

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

-1.2
Solubility 9.66 mg/ml ; 0.0627 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.

-6.1 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

2.0 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)

1.85

Application In Synthesis of [ 39745-39-6 ]

* 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 [ 39745-39-6 ]
  • Downstream synthetic route of [ 39745-39-6 ]

[ 39745-39-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 21901-29-1 ]
  • [ 39745-39-6 ]
YieldReaction ConditionsOperation in experiment
77% at 0℃; for 16 h; Synthesis of the compound 25 The compound 24 (10g, 0.065 mol) was added into 100 mL of water, a concentrated sulphuric acid (12 mL) was slowly added with agitation and cooled to 0 °C in an ice bath. Sodium nitrite (6.9 g, 0.098 mol) was added in batches, reacted at 0°C for 4h, and left standing for 12 h. A large amount of yellow precipitate was precipitated, filtrated under the reduced pressure, vacuum-dried to obtain 7.7 g of a yellow product with a yield of 77percent. The melting point is 216.5-218.5°C (water).
References: [1] Patent: EP2366691, 2011, A1, . Location in patent: Page/Page column 11.
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 3828,3830.
  • 2
  • [ 14011-21-3 ]
  • [ 41125-09-1 ]
  • [ 39745-39-6 ]
References: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4288 - 4312.
  • 3
  • [ 21901-29-1 ]
  • [ 39745-39-6 ]
  • [ 56057-19-3 ]
References: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66.
[2] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821.
[3] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66.
[4] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821.
  • 4
  • [ 1824-81-3 ]
  • [ 39745-39-6 ]
References: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66.
[2] Patent: EP2366691, 2011, A1, .
  • 5
  • [ 109-06-8 ]
  • [ 39745-39-6 ]
References: [1] Journal of the American Chemical Society, 1947, vol. 69, p. 63,66.
  • 6
  • [ 56057-19-3 ]
  • [ 21203-68-9 ]
  • [ 39745-39-6 ]
References: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 596,598.
  • 7
  • [ 70959-85-2 ]
  • [ 39745-39-6 ]
  • [ 39073-14-8 ]
References: [1] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 6, p. 1815 - 1821.
  • 8
  • [ 3279-76-3 ]
  • [ 39745-39-6 ]
References: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 1013,1024.
 

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