(R)-2-(4-Amino-4-carboxybut-1-en-1-yl)benzoic acid

ID: ALA3235236

PubChem CID: 90670681

Max Phase: Preclinical

Molecular Formula: C12H13NO4

Molecular Weight: 235.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@H](C/C=C/c1ccccc1C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C12H13NO4/c13-10(12(16)17)7-3-5-8-4-1-2-6-9(8)11(14)15/h1-6,10H,7,13H2,(H,14,15)(H,16,17)/b5-3+/t10-/m1/s1

Standard InChI Key:  YPRBPHJENZUXOP-RXNUUUNCSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    4.3638   -3.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -5.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3638   -5.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -5.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0688   -2.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547   -2.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7779   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4870   -4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1961   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9010   -4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6101   -3.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6101   -3.1640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3192   -4.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9010   -5.2070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  2  7  2  0
  1  8  2  0
  1  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 14 15  2  0
 14 16  1  0
 13 14  1  0
 13 17  1  6
  3 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3235236

   2-[(E,4R)-4-amino-4-carboxybut-1-enyl]benzoic 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: 235.24

Molecular Weight (Monoisotopic): 235.0845

AlogP: 1.20

#Rotatable Bonds: 5

Polar Surface Area: 100.62

Molecular Species: ZWITTERION

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.78

CX Basic pKa: 9.48

CX LogP: -1.00

CX LogD: -4.18

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.71

Np Likeness Score: 0.61

References

1. Pinto A, Tamborini L, Mastronardi F, Ettari R, Romano D, Nielsen B, De Micheli C, Conti P..  (2014)  Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors.,  24  (8): [PMID:24630559] [10.1016/j.bmcl.2014.02.058]

Source

Source(1):

• Scientific Literature