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

ID: ALA3559476

PubChem CID: 118753798

Max Phase: Preclinical

Molecular Formula: C17H30N2O3

Molecular Weight: 310.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCC[N+](C)(C)C)C(=O)[O-]

Standard InChI:  InChI=1S/C17H30N2O3/c1-17(2)12-13(17)15(20)18-14(16(21)22)10-8-6-7-9-11-19(3,4)5/h10,13H,6-9,11-12H2,1-5H3,(H-,18,20,21,22)/b14-10-/t13-/m1/s1

Standard InChI Key:  NOSQAJGISWGCEY-JFBXQDQPSA-N

Molfile:  

     RDKit          2D

 23 23  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
    0.4253   -3.8447    0.0000 C   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
   -0.8214   -3.1442    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
    2.8648   -2.3769    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
    6.4522   -2.4571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  1  4  1  1
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8 15  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 20  1  0
 16  8  1  0
 17  8  1  0
 18  8  1  0
 19 11  1  0
 20 22  1  0
 21 19  1  0
 22 21  1  0
  2  3  1  0
  1 23  1  6
M  CHG  2   8   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3559476

   ---

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: 310.44

Molecular Weight (Monoisotopic): 310.2256

AlogP: 1.05

#Rotatable Bonds: 9

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: 3.75

CX Basic pKa: ┄

CX LogP: -2.16

CX LogD: -1.39

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.39

Np Likeness Score: 0.91

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