2-(3-Phenyl-acryloylamino)-but-2-enoic acid

ID: ALA269648

PubChem CID: 44267720

Max Phase: Preclinical

Molecular Formula: C13H13NO3

Molecular Weight: 231.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\NC(=O)/C=C/c1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C13H13NO3/c1-2-11(13(16)17)14-12(15)9-8-10-6-4-3-5-7-10/h2-9H,1H3,(H,14,15)(H,16,17)/b9-8+,11-2-

Standard InChI Key:  YUMSWZVJJPYPJL-JHCROYGQSA-N

Molfile:  

     RDKit          2D

 17 17  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
    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
    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
    5.1167   -4.0792    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
    4.7042   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9417   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3542   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -5.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -5.5125    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  4  1  0
  6  5  2  0
  7  2  2  0
  8  1  2  0
  9  4  2  0
 10  2  1  0
 11  6  1  0
 12  8  1  0
 13 11  2  0
 14 11  1  0
 15 14  2  0
 16 13  1  0
 17 15  1  0
 16 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA269648

   (Z)-2-[[(E)-3-phenylprop-2-enoyl]amino]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: 231.25

Molecular Weight (Monoisotopic): 231.0895

AlogP: 1.80

#Rotatable Bonds: 4

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: 4.00

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: -1.21

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.78

Np Likeness Score: -0.11

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