Benzyl-{9-carboxy-9-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-non-8-enyl}-dimethyl-ammonium

ID: ALA3559630

PubChem CID: 118753927

Max Phase: Preclinical

Molecular Formula: C25H38N2O3

Molecular Weight: 414.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC1C(=O)N/C(=C\CCCCCCC[N+](C)(C)Cc1ccccc1)C(=O)[O-]

Standard InChI:  InChI=1S/C25H38N2O3/c1-25(2)18-21(25)23(28)26-22(24(29)30)16-12-7-5-6-8-13-17-27(3,4)19-20-14-10-9-11-15-20/h9-11,14-16,21H,5-8,12-13,17-19H2,1-4H3,(H-,26,28,29,30)/b22-16-

Standard InChI Key:  OFXLNPOJWCZAOJ-JWGURIENSA-N

Molfile:  

     RDKit          2D

 30 31  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
    4.4559   -0.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -4.5559    0.0000 N   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
   -2.0591   -5.2687    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
    4.9894   -3.6306    0.0000 C   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
   -2.8844   -5.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -4.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4717   -4.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2341   -3.9682    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
   -3.2970   -4.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2970   -5.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -3.8557    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
    1.6548   -3.1137    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
    0.4252   -3.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1224   -5.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1141   -4.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5350   -5.2437    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  6  1  0
  8 17  1  0
  9  4  2  0
 10  7  2  0
 11  6  2  0
 12  8  1  0
 13  7  1  0
 14  2  1  0
 15  2  1  0
 16 12  1  0
 17 23  1  0
 18  8  1  0
 19  8  1  0
 20 11  1  0
 21 16  2  0
 22 16  1  0
 23 27  1  0
 24 20  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 22  2  0
 29 21  1  0
 30 28  1  0
  2  3  1  0
 29 30  2  0
M  CHG  2   8   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559630

   ---

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: 414.59

Molecular Weight (Monoisotopic): 414.2882

AlogP: 3.40

#Rotatable Bonds: 13

Polar Surface Area: 69.23

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.30

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: 1.22

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: 0.51

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