Home Cart Sign in  
Chemical Structure| 20271-20-9 Chemical Structure| 20271-20-9

Structure of 20271-20-9

Chemical Structure| 20271-20-9

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 20271-20-9 ]

CAS No. :20271-20-9
Formula : C5H5N3O4
M.W : 171.11
SMILES Code : O=C(C1=C([N+]([O-])=O)NC=N1)OC
MDL No. :MFCD01105422
InChI Key :YGTWILAKCGDEML-UHFFFAOYSA-N
Pubchem ID :86222852

Safety of [ 20271-20-9 ]

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

Computational Chemistry of [ 20271-20-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 5
Fraction Csp3 0.2
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 38.69
TPSA ?

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

100.8 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.59
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

0.41
Log Po/w (WLOGP)?

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

0.1
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.

-0.97
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

-1.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.22

Water Solubility

Log S (ESOL):?

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

-1.27
Solubility 9.2 mg/ml ; 0.0538 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.

-2.09
Solubility 1.38 mg/ml ; 0.00806 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

-0.69
Solubility 35.1 mg/ml ; 0.205 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.

-7.05 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)

2.34

Application In Synthesis of [ 20271-20-9 ]

* 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 [ 20271-20-9 ]
  • Downstream synthetic route of [ 20271-20-9 ]

[ 20271-20-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 20271-20-9 ]
  • [ 4919-00-0 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen In methanol; ethanol for 4 h; A solution of Description 17 (1.24g, 7. 25 mmol) in1 : 1 ethanol : methanol (60 ml) was hydrogenated using 10 percent palladium on carbon catalyst under a balloon of hydrogen. After 4 h the reaction mixture was filtered, the filtrate condensed and azeotroped with ethanol. The product was triturated with ethyl acetate and dried to give the title compound as a white solid (0.98 g, 96percent).'H NMR (400 MHz, DMSO)8 12.0(1H, brs), 7.32(1H, s), 5.56 (2H, s), 3.70 (3H, s). Mlz (ES+) 142 (M+H+).
References: [1] Patent: WO2005/49613, 2005, A1, . Location in patent: Page/Page column 44.
[2] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2401;engl.Ausg.S.2366.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 20271-20-9 ]

Esters

Chemical Structure| 51605-32-4

A211377 [51605-32-4]

Ethyl 5-methyl-1H-imidazole-4-carboxylate

Similarity: 0.63

Chemical Structure| 3304-70-9

A344282 [3304-70-9]

Dimethyl 4,5-imidazoledicarboxylate

Similarity: 0.63

Chemical Structure| 137159-36-5

A345095 [137159-36-5]

Ethyl 5-formyl-1H-imidazole-4-carboxylate

Similarity: 0.62

Chemical Structure| 1093261-46-1

A576869 [1093261-46-1]

Methyl 5-bromo-1H-imidazole-4-carboxylate

Similarity: 0.62

Chemical Structure| 1080-79-1

A147481 [1080-79-1]

Diethyl 1H-imidazole-4,5-dicarboxylate

Similarity: 0.62

Nitroes

Chemical Structure| 81246-34-6

A541431 [81246-34-6]

5-Nitro-1H-imidazole-4-carbaldehyde

Similarity: 0.79

Chemical Structure| 14003-66-8

A162282 [14003-66-8]

4-Methyl-5-nitro-1H-imidazole

Similarity: 0.71

Chemical Structure| 40507-59-3

A250070 [40507-59-3]

4-Nitro-1H-imidazole-5-carboxylic acid

Similarity: 0.70

Chemical Structure| 38923-08-9

A126945 [38923-08-9]

Ethyl 6-nitroimidazo[1,2-a]pyridine-2-carboxylate

Similarity: 0.61

Chemical Structure| 865998-46-5

A105132 [865998-46-5]

Ethyl 5-nitro-1H-imidazole-2-carboxylate

Similarity: 0.60