(R)-2-[(2,2-Dimethyl-cyclopropanecarbonyl)-amino]-oct-2-enoic acid

ID: ALA2092843

PubChem CID: 70693401

Max Phase: Preclinical

Molecular Formula: C14H23NO3

Molecular Weight: 253.34

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H23NO3/c1-4-5-6-7-8-11(13(17)18)15-12(16)10-9-14(10,2)3/h8,10H,4-7,9H2,1-3H3,(H,15,16)(H,17,18)/b11-8-/t10-/m0/s1

Standard InChI Key:  WIESNNVNXBYTFK-DFYQSJSGSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.6113   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -2.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3402   -2.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782   -1.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3536   -1.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9163   -0.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3036    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5655   -0.6164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917   -0.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282    0.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -2.6405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4156   -3.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2957   -1.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203   -1.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3322   -2.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5076   -2.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7320   -2.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  1  4  1  6
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  4  2  0
  9  7  2  0
 10  6  2  0
 11  7  1  0
 12  2  1  0
 13  2  1  0
 14 10  1  0
 15 14  1  0
 16 17  1  0
 17 15  1  0
 18 16  1  0
  2  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2092843

   (Z)-2-[[(1R)-2,2-dimethylcyclopropanecarbonyl]amino]oct-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: 253.34

Molecular Weight (Monoisotopic): 253.1678

AlogP: 2.70

#Rotatable Bonds: 7

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.40

CX Basic pKa: ┄

CX LogP: 2.73

CX LogD: -0.16

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.54

Np Likeness Score: 0.93

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