(2S)-2-[[(4S)-2-(carboxymethyl)-3-oxo-4,5-dihydro-1H-2-benzazepin-4-yl]amino]-4-phenyl-butanoic acid

ID: ALA5279614

Max Phase: Preclinical

Molecular Formula: C22H24N2O5

Molecular Weight: 396.44

Names and Identifiers

Canonical SMILES:  O=C(O)CN1Cc2ccccc2C[C@H](N[C@@H](CCc2ccccc2)C(=O)O)C1=O

Standard InChI:  InChI=1S/C22H24N2O5/c25-20(26)14-24-13-17-9-5-4-8-16(17)12-19(21(24)27)23-18(22(28)29)11-10-15-6-2-1-3-7-15/h1-9,18-19,23H,10-14H2,(H,25,26)(H,28,29)/t18-,19-/m0/s1

Standard InChI Key:  WISWGINCJUEDBR-OALUTQOASA-N

Molfile:  

 
     RDKit          2D

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   -3.1391    2.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275    2.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0057   -1.6418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2946   -1.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4356   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1069    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697    0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9847    1.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671    0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9253    0.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3973   -0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848   -1.3022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7656   -1.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5591   -1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400   -2.2513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.8769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -1.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -2.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0
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  9 10  1  0
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 16 21  2  0
 21 22  1  0
 23 22  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 28 23  1  0
 28 14  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5279614

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 396.44

Molecular Weight (Monoisotopic): 396.1685

AlogP: 1.70

#Rotatable Bonds: 8

Polar Surface Area: 106.94

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.11

CX Basic pKa: 7.92

CX LogP: -0.27

CX LogD: -3.21

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: 0.01

References

1. Van der Poorten O, Knuhtsen A, Sejer Pedersen D, Ballet S, Tourwé D..  (2016)  Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.,  59  (24): [PMID:27690430] [10.1021/acs.jmedchem.6b01029]

Source

Source(1):

• Scientific Literature