2-(2-Bromo-acetylamino)-acrylic acid

ID: ALA57490

PubChem CID: 19100250

Max Phase: Preclinical

Molecular Formula: C5H6BrNO3

Molecular Weight: 208.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)CBr)C(=O)O

Standard InChI:  InChI=1S/C5H6BrNO3/c1-3(5(9)10)7-4(8)2-6/h1-2H2,(H,7,8)(H,9,10)

Standard InChI Key:  IHEIFBUZWCNXJY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 10  9  0  0  0  0  0  0  0  0999 V2000
    1.3125   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0250   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -3.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -4.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -2.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5375   -3.0875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -3.5000    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 10  1  0
 10  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA57490

   2-[(2-Bromoacetyl)amino]prop-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: 208.01

Molecular Weight (Monoisotopic): 206.9531

AlogP: 0.10

#Rotatable Bonds: 3

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: 2.91

CX Basic pKa: ┄

CX LogP: -0.08

CX LogD: -3.57

Aromatic Rings: ┄

Heavy Atoms: 10

QED Weighted: 0.51

Np Likeness Score: 0.14

References

1. Wu YQ, Mobashery S..  (1991)  Targeting renal dipeptidase (dehydropeptidase I) for inactivation by mechanism-based inactivators.,  34  (6): [PMID:2061929] [10.1021/jm00110a025]

Source

Source(1):

• Scientific Literature