1-{7-Carboxy-7-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-6-enyl}-pyridinium

ID: ALA3559633

PubChem CID: 118753928

Max Phase: Preclinical

Molecular Formula: C19H26N2O3

Molecular Weight: 330.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC1C(=O)N/C(=C\CCCCC[n+]1ccccc1)C(=O)[O-]

Standard InChI:  InChI=1S/C19H26N2O3/c1-19(2)14-15(19)17(22)20-16(18(23)24)10-6-3-4-7-11-21-12-8-5-9-13-21/h5,8-10,12-13,15H,3-4,6-7,11,14H2,1-2H3,(H-,20,22,23,24)/b16-10-

Standard InChI Key:  CLCVEWPDMMVFQY-YBEGLDIGSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    5.7689   -3.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7897   -3.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942   -3.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3312   -2.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5059   -2.3426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0682   -1.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -3.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4559   -0.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189   -1.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0265   -0.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2512   -1.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2812   -0.9003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -4.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9894   -3.6306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -3.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -3.1512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961   -4.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8636   -2.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8295   -3.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -2.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6214   -4.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -3.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548   -3.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -3.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  5  1  0
  7 15  1  0
  8  6  1  0
  9  4  2  0
 10  8  2  0
 11  6  2  0
 12  8  1  0
 13  2  1  0
 14  2  1  0
 15 19  1  0
 16  7  2  0
 17  7  1  0
 18 11  1  0
 19 23  1  0
 20 18  1  0
 21 17  2  0
 22 16  1  0
 23 20  1  0
 24 21  1  0
  2  3  1  0
 22 24  2  0
M  CHG  2   7   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559633

   ---

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: 330.43

Molecular Weight (Monoisotopic): 330.1943

AlogP: 1.33

#Rotatable Bonds: 9

Polar Surface Area: 73.11

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: -1.38

CX LogD: -1.61

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.42

Np Likeness Score: 0.52

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