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Chemical Structure| 124-30-1 Chemical Structure| 124-30-1

Structure of 124-30-1

Chemical Structure| 124-30-1

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Product Details of [ 124-30-1 ]

CAS No. :124-30-1
Formula : C18H39N
M.W : 269.51
SMILES Code : CCCCCCCCCCCCCCCCCCN
MDL No. :MFCD00008159
InChI Key :REYJJPSVUYRZGE-UHFFFAOYSA-N
Pubchem ID :15793

Safety of [ 124-30-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H303-H304-H315-H318-H373-H410
Precautionary Statements:P260-P264-P273-P280-P301+P310-P302+P352-P305+P351+P338+P310-P312-P331-P332+P313-P391-P405-P501
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 124-30-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 16
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 91.35
TPSA ?

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

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

5.12
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

4.3
Log Po/w (WLOGP)?

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

6.21
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.

4.93
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

6.3
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.37

Water Solubility

Log S (ESOL):?

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

-3.16
Solubility 0.185 mg/ml ; 0.000686 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.

-4.56
Solubility 0.00743 mg/ml ; 0.0000276 mol/l
Class?

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

Moderately 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

-6.79
Solubility 0.0000437 mg/ml ; 0.000000162 mol/l
Class?

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

Poorly 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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

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

-4.89 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

1.0
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

1.0
Egan?

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

1.0
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

2.0
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<2.0
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)

2.3

Application In Synthesis of [ 124-30-1 ]

* 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 [ 124-30-1 ]

[ 124-30-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 7113-10-2 ]
  • [ 124-30-1 ]
  • N-octadecyl-2-phenylthiazole-4-carboxamide [ No CAS ]
  • 2
  • [ 6914-79-0 ]
  • [ 124-30-1 ]
  • [ 1266666-38-9 ]
  • 3
  • [ 6914-79-0 ]
  • [ 124-30-1 ]
  • [ 1266665-37-5 ]
  • 4
  • [ 3543-75-7 ]
  • [ 124-30-1 ]
  • [ 1609623-16-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 2 - 20℃;Inert atmosphere; 4-{5-[Bis-(2-chloro-ethyl)-amino]-l-methyl-lH-benzoimidazol-2-yl}-N-octadecyl-butyramide (<strong>[3543-75-7]bendamustine</strong> Cjg amide): A 250 mL three neck round bottom flask equipped with a stir bar, thermocouple, cooling bath, 60 mL pressure equalizing dropping funnel and nitrogen in/outlet was charged with 10.0 g (25.3 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 10.6 g (27.8 mmol) of HATU and 100 mL of Nu,Nu-dimethylfomramide (DMF). To this stirred yellow solution was added 4.41 mL (3.27 g, 25.3 mmol) of Nu,Nu-diisopropylethyelamine (DIPEA). An exotherm to 27.1C was noted and the solution became a darker yellow. The reaction was cooled to 2.0C where a suspension of 6.2 mL (4.59 g, 35.5 mmol) of DIPEA, 7.65 g (25.6 mmol) of octadecyl amine in 0 mL of DMF was added via pipet. Once addition was complete the reaction became very thick and difficult to stir. It was warmed to room temperature and the magnetic stir bar was replaced with an overhead stirrer. The batch was stirred at RT overnight after which time an in process analysis indicated the reaction was complete. The batch was quenched onto 300 mL of DI water and extracted with dichloromethane (2 X 150 mL). The organic phases were combined, washed with 10% sodium hydrogen phosphate (1 X 300 mL), 8% aqueous sodium bicarbonate (1 X 300 mL) and brine (1 X 300 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo. The residue was purified by chromatography using lOOg of silica gel 60, 230-400 mesh, eluting with 1% MeOH/MDC (2 L), 2.5 % MeOH/MDC (1L) and 5% MeOH/MDC (1L) collecting -100 mL fractions. The product containing fractions were combined and concentrated to dryness in vacuo to yield 5.1 1 g (8.38 mmol, 33%) of the desired product as a white solid with an HPLC purity of 90.9A%. The major impurity was shown to be the C-16 amide which results from an impurity in the starting amine. XH NMR (400 MHz, DMSO-d6) delta 7.72 (s, b, 1H), 7.33 (d, J= 8.84 Hz, 1H), 6.91 (d, J= 2.22 Hz, 1H), 6.80 (dd, J= 2.36, 8.84 Hz), 3.71 (s, 8H), 3.70 (s, 3H), 3.01 (q, J= 6.8, 12.68, 2H), 2.79 (t, J= 7.44 Hz, 2H), 2.18 (t, J= 7.36 Hz, 2H), 1.97 (m, 2H), 1.36 (m, 2H), 1.28 (s, b, 30H), 0.85 (t, J= 6.32 Hz, 3H).
  • 5
  • [ 117-78-2 ]
  • [ 124-30-1 ]
  • [ 143657-39-0 ]
  • 6
  • [ 104091-08-9 ]
  • [ 124-30-1 ]
  • C42H64N2O5 [ No CAS ]
  • 7
  • [ 6492-86-0 ]
  • [ 124-30-1 ]
  • 4-amino-N-octadecyl-1,8-naphthalimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.3% In ethanol; for 12h;Reflux; n-Octadecylamine (538 mg,1.2 mmol)was added into a solutionof <strong>[6492-86-0]4-amino-1,8-naphthalic anhydride</strong> (213 mg,1.0 mmol) in ethanol(30 mL). The reaction mixture was stirred at reflux for 12 h. Afterthe mixture was cooled to room temperature, the solvent wasremoved under reduced pressure. The crude product was purifiedvia column chromatography (silica gel, dichloromethane) to give350 mg of 2a as a yellow solid in 75.3% yield. M.p. 132-133 C; 1HNMR (500 MHz, CDCl3): delta 8.59 (dd, 1H, J 1.0 Hz), 8.41 (d, 1H,J 8.5 Hz), 8.10 (dd, 1H, J 1.0 Hz), 7.65 (dd, 1H,J 7.0 Hz J 7.5 Hz), 6.88 (d, 1H, J 8.0 Hz), 4.95 (s, 2H), 4.15 (t, 2H,J 7.3 Hz), 1.71 (m, 2H), 1.41 (m, 2H), 1.26 (m, 28H), 0.88 (t, 3H,J 7.0 Hz); 13C NMR (125 MHz, CDCl3): delta 164.6, 164.0, 148.9, 133.7,131.4, 129.8, 126.7, 125.0, 123.3, 120.1, 112.1, 109.6, 77.3, 77.0, 76.8,40.3, 31.9, 29.7, 29.7, 29.6, 29.6, 29.5, 29.4, 28.2, 27.2, 22.7, 14.1; EPIMSC30H44N2O2 ([M+H]+): calcd 465.3, found 465.5; Elem. anal. forC30H44N2O2: calcd C 77.54, H 9.54, O 6.89; found C 77.34, H 9.76, O6.92%.
  • 8
  • [ 6492-86-0 ]
  • [ 124-30-1 ]
  • C58H88N2O4 [ No CAS ]
 

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