1-[2-ammonio-3-(1H-indol-2-yl)propanoyl]pyrrolidine-2-carboxylate

ID: ALA2371155

PubChem CID: 73345537

Max Phase: Preclinical

Molecular Formula: C16H19N3O3

Molecular Weight: 301.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](Cc1cc2ccccc2[nH]1)C(=O)N1CCC[C@H]1C(=O)O

Standard InChI:  InChI=1S/C16H19N3O3/c17-12(15(20)19-7-3-6-14(19)16(21)22)9-11-8-10-4-1-2-5-13(10)18-11/h1-2,4-5,8,12,14,18H,3,6-7,9,17H2,(H,21,22)/t12-,14-/m0/s1

Standard InChI Key:  MMBUAIXQUYZHKE-JSGCOSHPSA-N

Molfile:  

     RDKit          2D

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   -0.4456    0.3831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3484    1.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3041    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6820    2.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7039   -0.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8741    1.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9064    1.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    2.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -0.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874   -1.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5284   -0.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    1.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8538    0.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4415    1.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    1.8991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9064    3.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1558    2.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7310    3.3359    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  1  0
  6  2  1  0
  7  3  2  0
  5  8  1  1
  6  9  1  1
 10  4  1  0
 11  7  1  0
 12  6  1  0
 13  2  2  0
 14  8  1  0
 15  8  2  0
 16  1  1  0
 17  5  1  0
 18 16  1  0
 19 10  1  0
 20 11  1  0
 21 19  2  0
 22 20  2  0
 17 18  1  0
 10 11  2  0
 22 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2371155

   (2S)-1-[(2S)-2-amino-3-(1H-indol-2-yl)propanoyl]pyrrolidine-2-carboxylic 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: 301.35

Molecular Weight (Monoisotopic): 301.1426

AlogP: 1.11

#Rotatable Bonds: 4

Polar Surface Area: 99.42

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: 8.07

CX LogP: -1.66

CX LogD: -1.73

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.32

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