{7-Carboxy-7-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-6-enyl}-(2-hydroxy-ethyl)-dimethyl-ammonium

ID: ALA3559622

PubChem CID: 118753924

Max Phase: Preclinical

Molecular Formula: C18H32N2O4

Molecular Weight: 340.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H32N2O4/c1-18(2)13-14(18)16(22)19-15(17(23)24)9-7-5-6-8-10-20(3,4)11-12-21/h9,14,21H,5-8,10-13H2,1-4H3,(H-,19,22,23,24)/b15-9-

Standard InChI Key:  LZXNOKQBOBWIFK-DHDCSXOGSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.7712   -3.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7921   -3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4968   -3.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3334   -2.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078   -2.3435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -1.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4577   -0.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003   -3.8572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526   -1.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2834   -0.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -4.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9914   -3.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0266   -5.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8006   -4.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4253   -3.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2260   -3.8572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -3.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648   -2.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6263   -4.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299   -3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0558   -2.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -3.1150    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  7  1  0
 13  2  1  0
 14  2  1  0
 15 21  1  0
 16  8  1  0
 17 22  1  0
 18  8  1  0
 19  8  1  0
 20 11  1  0
 21 16  1  0
 22 24  1  0
 23 20  1  0
 24 23  1  0
  2  3  1  0
M  CHG  2   8   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559622

   ---

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: 340.46

Molecular Weight (Monoisotopic): 340.2362

AlogP: 0.41

#Rotatable Bonds: 11

Polar Surface Area: 89.46

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.75

CX Basic pKa: ┄

CX LogP: -2.85

CX LogD: -2.08

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.32

Np Likeness Score: 0.86

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