2-{[2-ammonio-3-(1H-indol-2-yl)propanoyl]amino}propanoate

ID: ALA2371156

PubChem CID: 73354637

Max Phase: Preclinical

Molecular Formula: C14H17N3O3

Molecular Weight: 275.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@@H](N)Cc1cc2ccccc2[nH]1)C(=O)O

Standard InChI:  InChI=1S/C14H17N3O3/c1-8(14(19)20)16-13(18)11(15)7-10-6-9-4-2-3-5-12(9)17-10/h2-6,8,11,17H,7,15H2,1H3,(H,16,18)(H,19,20)/t8-,11-/m0/s1

Standard InChI Key:  SEFYPIWRSANQPZ-KWQFWETISA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -2.4333    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875    0.8708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -0.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7208   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3250    2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -0.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -0.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083   -1.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5625    1.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7375    2.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9833    2.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5708    2.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4  3  1  0
  5  1  2  0
  6 11  1  0
  7  2  1  0
  8  1  1  0
  9  8  1  1
 10  5  1  0
 11  4  1  0
 12  9  1  0
 13  6  1  0
 14  3  2  0
 15  6  2  0
 16  7  1  0
 17 10  1  0
 11 18  1  6
 19 16  2  0
 20 17  2  0
  7 10  2  0
 20 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371156

   (2S)-2-[[(2S)-2-amino-3-(1H-indol-2-yl)propanoyl]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: 275.31

Molecular Weight (Monoisotopic): 275.1270

AlogP: 0.63

#Rotatable Bonds: 5

Polar Surface Area: 108.21

Molecular Species: ACID

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.71

CX Basic pKa: 8.08

CX LogP: -1.93

CX LogD: -2.01

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: -0.18

References

1. Gebauer S, Knütter I, Hartrodt B, Brandsch M, Neubert K, Thondorf I..  (2003)  Three-dimensional quantitative structure-activity relationship analyses of peptide substrates of the mammalian H+/peptide cotransporter PEPT1.,  46  (26): [PMID:14667225] [10.1021/jm030976x]

Source

Source(1):

• Scientific Literature