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Chemical Structure| 929-17-9 Chemical Structure| 929-17-9

Structure of 7-Aminoheptanoic acid
CAS No.: 929-17-9

Chemical Structure| 929-17-9

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Product Details of [ 929-17-9 ]

CAS No. :929-17-9
Formula : C7H15NO2
M.W : 145.20
SMILES Code : O=C(O)CCCCCCN
MDL No. :MFCD00008242
InChI Key :XDOLZJYETYVRKV-UHFFFAOYSA-N
Pubchem ID :13580

Safety of [ 929-17-9 ]

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

Computational Chemistry of [ 929-17-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 0
Fraction Csp3 0.86
Num. rotatable bonds 6
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 40.24
TPSA ?

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

63.32 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.41
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

-3.03
Log Po/w (WLOGP)?

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

0.98
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.

0.75
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

0.59
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.14

Water Solubility

Log S (ESOL):?

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

1.56
Solubility 5330.0 mg/ml ; 36.7 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

2.26
Solubility 26600.0 mg/ml ; 183.0 mol/l
Class?

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

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

-1.3
Solubility 7.26 mg/ml ; 0.05 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.

-9.34 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

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<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)

1.3

Application In Synthesis of [ 929-17-9 ]

* 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.

  • Downstream synthetic route of [ 929-17-9 ]

[ 929-17-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1184-90-3 ]
  • [ 929-17-9 ]
  • [ 73427-55-1 ]
  • 2
  • [ 1184-90-3 ]
  • [ 113-00-8 ]
  • [ 67-63-0 ]
  • [ 929-17-9 ]
  • 7-guanidinoheptanoic acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In hydrogenchloride; water; A. 7-Guanidinoheptanoic acid is prepared essentially by the method of Miller, et al, Synthesis, 777 (1986), which is incorporated herein by reference. 0.50 g of 7-aminoheptanoic acid is dissolved in a solution of 0.475 g of potassium carbonate in 3.5 ml of water. 0.427 g of <strong>[1184-90-3]aminoiminomethanesulfonic acid</strong> is added portionwise over 10 minutes and the mixture stirred at room temperature for 24 hours. The resulting solid is collected by filtration. The guanidine is dissolved in diluted hydrochloric acid and the solution evaporated in vacuo. Two portions of 2-propanol are evaporated from the residue to give 7-guanidinoheptanoic acid hydrochloride.
  • 3
  • [ 4521-22-6 ]
  • [ 929-17-9 ]
  • C18H27NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The carboxylic acid of compound 533 (obtainable from SALOR, catalogue number S532649) is activated with one equivalent of EDC and 1.2 equivalents of NHS in DMSO for 4h at 30 0C prior to addition of ten equivalents of 7-aminoheptanoic acid and triethylamine. The reaction is stirred overnight at 30 C, to yield 533-aminoheptanoic acid. The product is purified by HPLC and analysed by mass-spectrometry.
  • 4
  • [ 27913-58-2 ]
  • [ 929-17-9 ]
  • [ 1023970-53-7 ]
YieldReaction ConditionsOperation in experiment
Figure 1 shows possible building-block reagents, starting from which the compounds of the inventions may be synthesised. The carboxylic acid of compound 428 (obtainable from SIGMA, catalogue number 15634) was activated with one equivalent of EDC and 1.2 equivalents of NHS in DMSO for 4h at 30 0C prior to addition of ten equivalents of 7-aminoheptanoic acid and triethylamine. The reaction was stirred overnight at 30 C, to EPO <DP n="44"/>yield 428-aminoheptanoic acid. The product was purified by HPLC (see Example 21, General Methods) and analysed by mass-spectrometry.
In one preparation, 428-aminoheptanoic acid: 10 mumol of 428 were stirred with 8 mumol of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) and 10 mumol of N- hydroxysuccinimide (NHS) in 50 mul of DMSO for 3 hours at 30 0C followed by addition of 20 mumol of 7-aminoheptanoic acid (Bachem) in 100 mul of 1 M NaHCO3, pH 9. The reaction was allowed to stir overnight at 30 0C. After quenching of remaining reagents with excess of Trizma base the reaction was purified by HPLC and characterized by mass spectrometry.
  • 5
  • [ 1426827-79-3 ]
  • [ 929-17-9 ]
  • C18H27NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In water; acetonitrile; for 4h; To a solution of BCN-OSu derivative 51 in MeCN (5 mL) were added 7-aminoheptanoic acid 50 (145 mg, 1.0 mmol) in 0.1 M aqueous NaHCO3 (30 mL) and MeCN (25 mL). The mixture was stirred for 4 h and partially concentrated. Aqueous saturated NH4C1 (30 mL) was added and after extraction with DCM (2 x 30 mL), the combined organics were dried (Na2SO4) and concentrated. Product 52 was used in the step without furtherpurification. ‘H NIVIR (400 IVIHz, CDC13) (ppm) 4.68 (bs, 1H), 4.14 (d, J 7.9 Hz, 2H),3.17 (dd, J= 12.8, 6.3 Hz, 2H), 2.35 (t, J= 7.5 Hz, 2H), 2.32-2.09 (m, 6H), 1.70-1.25 (m, 1 1H), 0.94 (t, J 9.7 Hz, 2H).
 

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