(S)-2-(2-Benzylamino-3-phenyl-propionylamino)-propionic acid

ID: ALA2371834

PubChem CID: 73345599

Max Phase: Preclinical

Molecular Formula: C19H22N2O3

Molecular Weight: 326.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@H](Cc1ccccc1)NCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C19H22N2O3/c1-14(19(23)24)21-18(22)17(12-15-8-4-2-5-9-15)20-13-16-10-6-3-7-11-16/h2-11,14,17,20H,12-13H2,1H3,(H,21,22)(H,23,24)/t14-,17-/m0/s1

Standard InChI Key:  QJQSDYMCCOCSDF-YOEHRIQHSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  1  0  0  0  0  0999 V2000
    1.5375   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -2.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -1.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -3.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  1  0
  4  1  1  0
  5  2  1  0
  6  4  1  0
  7  1  2  0
  8  3  2  0
  4  9  1  6
 10  6  1  0
 11  3  1  0
 12  9  1  0
 13 10  1  0
  5 14  1  6
 15 12  1  0
 16 12  2  0
 17 13  1  0
 18 13  2  0
 19 16  1  0
 20 15  2  0
 21 17  2  0
 22 18  1  0
 23 19  2  0
 24 22  2  0
 23 20  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371834

   (2S)-2-[[(2S)-2-(benzylamino)-3-phenylpropanoyl]amino]propanoic 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: 326.40

Molecular Weight (Monoisotopic): 326.1630

AlogP: 1.98

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.69

CX Basic pKa: 8.18

CX LogP: 0.23

CX LogD: 0.17

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: -0.32

References

1. Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I..  (2005)  Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1.,  48  (13): [PMID:15974593] [10.1021/jm048982w]

Source

Source(1):

• Scientific Literature