2-(4-Thiophen-2-yl-butyrylamino)-but-2-enoic acid

ID: ALA11953

PubChem CID: 44267721

Max Phase: Preclinical

Molecular Formula: C12H15NO3S

Molecular Weight: 253.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C(\NC(=O)CCCc1cccs1)C(=O)O

Standard InChI:  InChI=1S/C12H15NO3S/c1-2-10(12(15)16)13-11(14)7-3-5-9-6-4-8-17-9/h2,4,6,8H,3,5,7H2,1H3,(H,13,14)(H,15,16)/b10-2-

Standard InChI Key:  KIUKBQIQQWESNM-SGAXSIHGSA-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
    3.8875   -4.8792    0.0000 S   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
    4.7042   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.6917    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
    5.0417   -5.5542    0.0000 C   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
    4.4250   -6.1042    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   -2.6542    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
    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
  2  1  1  0
  3  1  1  0
  4  6  1  0
  5  3  1  0
  6 15  1  0
  7  4  1  0
  8  2  2  0
  9  6  2  0
 10  1  2  0
 11  9  1  0
 12  5  2  0
 13  2  1  0
 14  5  1  0
 15 16  1  0
 16 14  1  0
 17 10  1  0
  7 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA11953

   2-(4-Thiophen-2-yl-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: 253.32

Molecular Weight (Monoisotopic): 253.0773

AlogP: 2.18

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: -1.03

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.76

Np Likeness Score: -1.34

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