2-(4-Phenyl-butyrylamino)-but-2-enoic acid

ID: ALA12049

PubChem CID: 44267722

Max Phase: Preclinical

Molecular Formula: C14H17NO3

Molecular Weight: 247.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\NC(=O)CCCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C14H17NO3/c1-2-12(14(17)18)15-13(16)10-6-9-11-7-4-3-5-8-11/h2-5,7-8H,6,9-10H2,1H3,(H,15,16)(H,17,18)/b12-2-

Standard InChI Key:  QNGYLHKGSNNZBB-OIXVIMQBSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    3.4750   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -1.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750    0.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -1.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -0.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  2  2  0
  6  1  2  0
  7  4  2  0
  8  2  1  0
  9 13  1  0
 10  4  1  0
 11 10  1  0
 12  6  1  0
 13 11  1  0
 14  9  2  0
 15  9  1  0
 16 15  2  0
 17 14  1  0
 18 16  1  0
 17 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA12049

   2-(4-Phenyl-butyrylamino)-but-2-enoic 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: 247.29

Molecular Weight (Monoisotopic): 247.1208

AlogP: 2.11

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: -0.81

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.76

Np Likeness Score: -0.24

References

1. Graham DW, Ashton WT, Barash L, Brown JE, Brown RD, Canning LF, Chen A, Springer JP, Rogers EF..  (1987)  Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids.,  30  (6): [PMID:3495664] [10.1021/jm00389a018]

Source

Source(1):

• Scientific Literature