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2-(1-Carboxymethyl-2-oxo-azocan-3-ylamino)-4-phenyl-butyric acid

ID: ALA3350294

PubChem CID: 118718824

Max Phase: Preclinical

Molecular Formula: C19H26N2O5

Molecular Weight: 362.43

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(O)CN1CCCCC[C@@H](N[C@H](CCc2ccccc2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C19H26N2O5/c22-17(23)13-21-12-6-2-5-9-15(18(21)24)20-16(19(25)26)11-10-14-7-3-1-4-8-14/h1,3-4,7-8,15-16,20H,2,5-6,9-13H2,(H,22,23)(H,25,26)/t15-,16-/m1/s1

Standard InChI Key:  SLHZGQUSIZGOKT-HZPDHXFCSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    6.3625   -4.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -2.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -5.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -3.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -4.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -4.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -6.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -4.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -5.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  1  6
  7  5  1  1
  6  1  1  0
  7  4  1  0
  8  6  1  0
  9  2  2  0
 10  5  2  0
 11  8  2  0
 12  7  1  0
 13  5  1  0
 14  1  1  0
 15  8  1  0
 16 12  1  0
 17 16  1  0
 18  3  1  0
 19 17  2  0
 20 17  1  0
 21 14  1  0
 22 26  1  0
 23 19  1  0
 24 20  2  0
 25 24  1  0
 26 21  1  0
 18 22  1  0
 25 23  2  0
M  END

Alternative Forms

  1. Parent:

    ALA3350294

    ---

Associated Targets(Human)

ACE Tclin Angiotensin-converting enzyme (1423 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 362.43Molecular Weight (Monoisotopic): 362.1842AlogP: 1.52#Rotatable Bonds: 8
Polar Surface Area: 106.94Molecular Species: ACIDHBA: 4HBD: 3
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 3.20CX Basic pKa: 8.03CX LogP: -0.69CX LogD: -3.60
Aromatic Rings: 1Heavy Atoms: 26QED Weighted: 0.65Np Likeness Score: -0.07

References

1. Thorsett ED, Harris EE, Aster SD, Peterson ER, Snyder JP, Springer JP, Hirshfield J, Tristram EW, Patchett AA, Ulm EH..  (1986)  Conformationally restricted inhibitors of angiotensin converting enzyme: synthesis and computations.,  29  (2): [PMID:3005569] [10.1021/jm00152a014]
2. Gomez-Monterrey, I I, Beaumont, A A, Nemecek, P P, Roques, B P BP and Fournie-Zaluski, M C MC.  1994-06-10  New thiol inhibitors of neutral endopeptidase EC 3.4.24.11: synthesis and enzyme active-site recognition.  [PMID:8021926]
3. Michaud, A A, Williams, T A TA, Chauvet, M T MT and Corvol, P P.  1997-06  Substrate dependence of angiotensin I-converting enzyme inhibition: captopril displays a partial selectivity for inhibition of N-acetyl-seryl-aspartyl-lysyl-proline hydrolysis compared with that of angiotensin I.  [PMID:9187274]
4. Lefebvre, H P HP and 5 more authors.  2007  Angiotensin-converting enzyme inhibitors in veterinary medicine.  [PMID:17506720]
5. Robinson, Dean M DM, Curran, Monique P MP and Lyseng-Williamson, Katherine A KA.  2007  Imidapril: a review of its use in essential hypertension, Type 1 diabetic nephropathy and chronic heart failure.  [PMID:17547476]
6. Ceconi, Claudio C and 5 more authors.  2007-12-22  Angiotensin-converting enzyme (ACE) inhibitors have different selectivity for bradykinin binding sites of human somatic ACE.  [PMID:17716647]
7. Deaton, David N and 5 more authors.  2008-01-15  Thiol-based angiotensin-converting enzyme 2 inhibitors: P1 modifications for the exploration of the S1 subsite.  [PMID:18078750]
8. Deaton, David N; Graham, Kevin P; Gross, Jeffrey W and Miller, Aaron B.  2008-03-01  Thiol-based angiotensin-converting enzyme 2 inhibitors: P1' modifications for the exploration of the S1' subsite.  [PMID:18243695]
9. Grice, Cheryl A CA and 15 more authors.  2008-07-24  Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity.  [PMID:18588282]
10. Madsen, Julie L H JL and 5 more authors.  2012-09-13  Synthesis and evaluation of silanediols as highly selective uncompetitive inhibitors of human neutrophil elastase.  [PMID:22882079]
11. Day, Joshua A and Cohen, Seth M.  2013-10-24  Investigating the selectivity of metalloenzyme inhibitors.  [PMID:24074025]
12. Charton, Julie J and 16 more authors.  2014-05-22  Imidazole-derived 2-[N-carbamoylmethyl-alkylamino]acetic acids, substrate-dependent modulators of insulin-degrading enzyme in amyloid-β hydrolysis.  [PMID:24735644]
13. Sattigeri, Jitendra A JA and 20 more authors.  2017-06-01  Approaches towards the development of chimeric DPP4/ACE inhibitors for treating metabolic syndrome.  [PMID:28442252]
14. Manikandan, A A, Moharil, Pearl P, Sathishkumar, M M, Muñoz-Garay, C C and Sivakumar, A A.  2017-12-01  Therapeutic investigations of novel indoxyl-based indolines: A drug target validation and Structure-Activity Relationship of angiotensin-converting enzyme inhibitors with cardiovascular regulation and thrombolytic potential.  [PMID:29032034]
15. McKinnell, R Murray RM and 13 more authors.  2019-01-10  Discovery of TD-0212, an Orally Active Dual Pharmacology AT1 Antagonist and Neprilysin Inhibitor (ARNI).  [PMID:30655952]
16. Sharma, Urvashi; Cozier, Gyles E; Sturrock, Edward D and Acharya, K Ravi.  2020-05-28  Molecular Basis for Omapatrilat and Sampatrilat Binding to Neprilysin-Implications for Dual Inhibitor Design with Angiotensin-Converting Enzyme.  [PMID:32337993]

Source