Structure of 7-Aminoheptanoic acid
CAS No.: 929-17-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
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 |
63.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.41 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-3.03 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.75 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.59 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
1.56 |
Solubility | 5330.0 mg/ml ; 36.7 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (Ali)? Ali: Topological method implemented from |
2.26 |
Solubility | 26600.0 mg/ml ; 183.0 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.3 |
Solubility | 7.26 mg/ml ; 0.05 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-9.34 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
2.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.3 |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |