(S)-2-((S)-2-benzamido-3-phenylpropanamido)propanoic acid

ID: ALA214174

Cas Number: 65049-90-3

PubChem CID: 2282458

Max Phase: Preclinical

Molecular Formula: C19H20N2O4

Molecular Weight: 340.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C19H20N2O4/c1-13(19(24)25)20-18(23)16(12-14-8-4-2-5-9-14)21-17(22)15-10-6-3-7-11-15/h2-11,13,16H,12H2,1H3,(H,20,23)(H,21,22)(H,24,25)/t13-,16-/m0/s1

Standard InChI Key:  RTSMBLLZBBYZQP-BBRMVZONSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  1  0  0  0  0  0999 V2000
   10.4421  -27.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7107  -25.9743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7218  -26.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0146  -27.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4552  -28.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1513  -26.7789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9905  -25.5720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2571  -24.3473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774  -24.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6866  -24.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4068  -24.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1160  -24.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8363  -24.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8474  -25.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1382  -25.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4179  -25.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2813  -25.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5499  -24.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8296  -24.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1204  -24.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4002  -24.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891  -23.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0963  -23.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8165  -23.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5610  -25.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  3  1  0
  3  4  1  6
  1  5  2  0
  1  6  1  0
  9  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
  7 17  2  0
  2  7  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 18 25  2  0
  8 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214174

   (2S)-2-[[(2S)-2-benzamido-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: 340.38

Molecular Weight (Monoisotopic): 340.1423

AlogP: 1.62

#Rotatable Bonds: 7

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.67

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: -1.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.31

References

1. Biegel A, Gebauer S, Brandsch M, Neubert K, Thondorf I..  (2006)  Structural requirements for the substrates of the H+/peptide cotransporter PEPT2 determined by three-dimensional quantitative structure-activity relationship analysis.,  49  (14): [PMID:16821788] [10.1021/jm0601811]

Source

Source(1):

• Scientific Literature