3-ammonio-3-(1-benzyloxycarbonylethylcarbamoyl)propanoate

ID: ALA2372648

PubChem CID: 53863424

Max Phase: Preclinical

Molecular Formula: C14H18N2O5

Molecular Weight: 294.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NC(=O)[C@@H](N)CC(=O)O)C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C14H18N2O5/c1-9(16-13(19)11(15)7-12(17)18)14(20)21-8-10-5-3-2-4-6-10/h2-6,9,11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t9-,11+/m1/s1

Standard InChI Key:  GYBJWJZGVCGRAI-KOLCDFICSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   10.4233   -9.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7088   -9.4797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8522   -9.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5667   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9943   -9.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1377  -10.3047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5654   -9.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4233   -8.2422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2811   -9.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2798  -10.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5667  -10.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8509   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -9.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9943   -8.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1364   -8.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -9.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075   -9.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4220   -7.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075   -8.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  5  3  1  6
  4  7  1  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8  5  1  0
  9  4  1  0
 10  1  2  0
 11  6  1  0
 12  4  2  0
 13  6  2  0
 14  9  1  0
 15 14  1  0
  7 16  1  1
 17 15  1  0
 18 15  2  0
 19 18  1  0
 20 17  2  0
 21 19  2  0
 21 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2372648

   (3S)-3-amino-4-oxo-4-[[(2R)-1-oxo-1-phenylmethoxypropan-2-yl]amino]butanoic 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: 294.31

Molecular Weight (Monoisotopic): 294.1216

AlogP: 0.04

#Rotatable Bonds: 7

Polar Surface Area: 118.72

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.42

CX Basic pKa: 8.53

CX LogP: -2.15

CX LogD: -2.18

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: 0.01

References

1. Tsang JW, Schmied B, Nyfeler R, Goodman M..  (1984)  Peptide sweeteners. 6. Structural studies on the C-terminal amino acid of L-aspartyl dipeptide sweeteners.,  27  (12): [PMID:6502595] [10.1021/jm00378a023]

2. 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