2-Benzyl-4-(1-carboxy-ethylcarbamoyl)-5-phenyl-pentanoic acid

ID: ALA2114199

PubChem CID: 14557664

Max Phase: Preclinical

Molecular Formula: C22H25NO5

Molecular Weight: 383.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CCNC(=O)[C@@H](Cc1ccccc1)C[C@H](Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C22H25NO5/c24-20(25)11-12-23-21(26)18(13-16-7-3-1-4-8-16)15-19(22(27)28)14-17-9-5-2-6-10-17/h1-10,18-19H,11-15H2,(H,23,26)(H,24,25)(H,27,28)/t18-,19-/m0/s1

Standard InChI Key:  JUUGRNXBMBREMY-OALUTQOASA-N

Molfile:  

     RDKit          2D

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    1.6688   -2.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -4.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -3.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -4.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0673   -5.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3342   -4.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -5.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -4.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992   -6.1031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -2.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0494   -6.1746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8442   -4.8455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -2.3959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773   -5.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301   -4.9051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2384   -3.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -6.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -6.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4589   -4.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503   -2.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -6.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -3.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4649   -2.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536   -7.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -7.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -7.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1741   -2.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  6
  3  1  1  1
  4  5  1  0
  5  3  1  0
  6  7  1  0
  7 15  1  0
  8  3  1  0
  9  4  1  0
 10  1  2  0
 11  2  2  0
 12  6  2  0
 13  1  1  0
 14  2  1  0
 15 13  1  0
 16  6  1  0
 17  9  1  0
 18  8  1  0
 19 18  1  0
 20 17  1  0
 21 17  2  0
 22 18  2  0
 23 20  2  0
 24 21  1  0
 25 22  1  0
 26 19  2  0
 27 25  2  0
 28 24  2  0
 26 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114199

   N-[(R*,R*)-2,4-dibenzyl-4-carboxybutyryl]-3-aminopropionic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 383.44

Molecular Weight (Monoisotopic): 383.1733

AlogP: 2.77

#Rotatable Bonds: 11

Polar Surface Area: 103.70

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.95

CX Basic pKa: ┄

CX LogP: 3.42

CX LogD: -2.45

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.04

References

1. Ksander GM, Diefenbacher CG, Yuan AM, Clark F, Sakane Y, Ghai RD..  (1989)  Enkephalinase inhibitors. 1. 2,4-Dibenzylglutaric acid derivatives.,  32  (12): [PMID:2585440] [10.1021/jm00132a005]

Source

Source(1):

• Scientific Literature