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Chemical Structure| 14618-78-1 Chemical Structure| 14618-78-1

Structure of 14618-78-1

Chemical Structure| 14618-78-1

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Product Details of [ 14618-78-1 ]

CAS No. :14618-78-1
Formula : C6H11NO2
M.W : 129.16
SMILES Code : N#CCCC(OC)OC
MDL No. :MFCD00019883
InChI Key :XJHNCGVHPLDMRK-UHFFFAOYSA-N
Pubchem ID :84558

Safety of [ 14618-78-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332
Precautionary Statements:P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312

Computational Chemistry of [ 14618-78-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 4
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 32.88
TPSA ?

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

42.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.53
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

0.14
Log Po/w (WLOGP)?

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

0.91
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.

-0.01
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

0.53
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.62

Water Solubility

Log S (ESOL):?

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

-0.46
Solubility 44.3 mg/ml ; 0.343 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.

-0.58
Solubility 33.7 mg/ml ; 0.261 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

-1.04
Solubility 11.8 mg/ml ; 0.091 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

Yes
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.

-6.99 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

1.0 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)

1.87

Application In Synthesis of [ 14618-78-1 ]

* 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.

  • Downstream synthetic route of [ 14618-78-1 ]

[ 14618-78-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 14618-78-1 ]
  • [ 35661-51-9 ]
  • C19H17N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In ethanol; water;Reflux; General procedure: One equiv. of carbazate was suspended in EtOH containing 10percent (by vol.) of water(approx. 5 ml per mmol of the carbazate) and 1.05 equiv. of the acetal or ketal wasadded, followed by the addition of 0.05 equiv. of TFA. The reaction mixture was heatedto reflux and the progress of the reaction was monitored by TLC (thin layer chromatographyon silica gel) using ethyl acetate or a mixture of ethyl acetate-light petroleummixture (for the correct eluent, see characterization data of the compounds). After thereaction was complete, the reaction mixture was cooled to about 45C and three (3)equiv. of acetic acid was added, followed by the dropwise addition of a THF solutionof three (3) equiv. of NaBH3CN (approx. 1 ml of THF per 1.5 mmol of NaBH3CN).The reaction mixture was stirred at approx. 45C for 80 min. Subsequently, the reactionmixture was cooled to room temperature, acidified using 0.5 M HCl aqueous solution(6 ml of 0.5 M HCl per 1 mmol of starting carbazate) and stirred until the liberation ofhydrogen ceased. The reaction mixture was neutralized (to pH 8) by the dropwise additionof a saturated NaHCO3 solution (4 ml per 1 mmol of carbazate). The volatileswere removed under reduced pressure at approx. 40C. The residue was dissolved inethyl acetate, washed with saturated NaHCO3, twice with water and finally with saturatedaqueous sodium chloride. The combined aqueous washes were extracted twicewith ethyl acetate (25 ml per 1 mmol of expected product) and the extracts werewashed with saturated aqueous sodium chloride and combined with the organic phase. After drying over anhydrous Na2SO4 and evaporation of the solvent under reduced pressure,the residue was purified by column chromatography on silica gel using ethyl acetate-light petroleum (1:1 or 1:2) or ethyl acetate as eluent. For specific informationabout the eluent used to monitor the progress of the reaction and for purification, seethe Rf data for each compound.
 

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