(1S)-2-[(2S)-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-1-carboxylic acid

ID: ALA5287967

Max Phase: Preclinical

Molecular Formula: C23H26N2O5

Molecular Weight: 410.47

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N1CCc2ccccc2[C@H]1C(=O)O

Standard InChI:  InChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-13-17-9-5-6-10-18(17)20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19-,20-/m0/s1

Standard InChI Key:  ZQEUYWFUMYARGJ-YSSFQJQWSA-N

Molfile:  

 
     RDKit          2D

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    2.1433   -2.6803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -1.0302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0001   -1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -2.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4291   -1.4428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -1.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1437   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8582    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    2.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719    2.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5719    1.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580   -1.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -1.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8580   -2.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  4  2  1  1
  5  4  1  0
  6  5  1  0
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  9  8  2  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  8 13  1  0
 14  5  1  0
 14 15  2  0
 16 14  1  0
 16 17  1  1
 18 16  1  0
 19 18  1  0
 19 20  1  6
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 22  2  0
 28 19  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287967

   ---

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: 410.47

Molecular Weight (Monoisotopic): 410.1842

AlogP: 2.26

#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: 3.04

CX Basic pKa: 7.80

CX LogP: 0.37

CX LogD: -2.71

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: 0.00

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