(1S)-2-[(2S)-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]propanoyl]isoindoline-1-carboxylic acid

ID: ALA5267769

Max Phase: Preclinical

Molecular Formula: C22H24N2O5

Molecular Weight: 396.44

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1Cc2ccccc2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C22H24N2O5/c1-14(23-18(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-13-16-9-5-6-10-17(16)19(24)22(28)29/h2-10,14,18-19,23H,11-13H2,1H3,(H,26,27)(H,28,29)/t14-,18-,19-/m0/s1

Standard InChI Key:  CUKQMSYVQGXHKG-JVPBZIDWSA-N

Molfile:  

 
     RDKit          2D

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   -1.9856   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    0.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    1.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    2.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    2.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825    2.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825    1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2709   -1.4102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -0.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -0.9976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -0.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786   -0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265   -1.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8401   -2.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6373   -2.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566   -2.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0068   -0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147   -0.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0027    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1584   -2.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001   -2.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4147   -0.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  3  4  1  0
  4  5  1  0
  6  5  2  0
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  9  8  1  0
 10  9  2  0
  5 10  1  0
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 13 14  1  0
 15 14  1  0
 15 16  1  0
 16 17  2  0
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 18 14  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 16 25  1  0
 13 26  2  0
 12 27  1  1
  1 28  2  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5267769

   ---

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: 2.22

#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: 3.00

CX Basic pKa: 7.80

CX LogP: 0.08

CX LogD: -3.03

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -0.03

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