(S)-2-[(2,2-Dimethyl-cyclopropanecarbonyl)-amino]-8-(1-phosphono-ethylamino)-oct-2-enoic acid

ID: ALA1907822

PubChem CID: 57400993

Max Phase: Preclinical

Molecular Formula: C16H29N2O6P

Molecular Weight: 376.39

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H29N2O6P/c1-11(25(22,23)24)17-9-7-5-4-6-8-13(15(20)21)18-14(19)12-10-16(12,2)3/h8,11-12,17H,4-7,9-10H2,1-3H3,(H,18,19)(H,20,21)(H2,22,23,24)/b13-8-/t11?,12-/m1/s1

Standard InChI Key:  JGWBZZGFKONACH-KZPJGYJXSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    5.7820   -3.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028   -3.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089   -3.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7896   -5.2932    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3433   -2.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5161   -2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775   -1.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4660   -0.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021   -4.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -5.2932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7318   -1.6084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0357   -0.2173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586   -1.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0293   -5.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718   -6.0076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011   -3.8644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2932   -0.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0007   -3.6388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814   -4.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4261   -3.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596   -2.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314   -3.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -3.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2922   -2.3846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  9  1  0
  1  5  1  1
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9 16  1  0
 10  4  2  0
 11  5  2  0
 12  8  2  0
 13  7  2  0
 14  4  1  0
 15  4  1  0
 16 22  1  0
 17  8  1  0
 18  2  1  0
 19  2  1  0
 20  9  1  0
 21 13  1  0
 22 24  1  0
 23 21  1  0
 24 25  1  0
 25 23  1  0
  2  3  1  0
  1 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1907822

   (Z)-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]-8-(1-phosphonoethylamino)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: 376.39

Molecular Weight (Monoisotopic): 376.1763

AlogP: 1.79

#Rotatable Bonds: 11

Polar Surface Area: 135.96

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -0.63

CX Basic pKa: 9.33

CX LogP: -0.90

CX LogD: -4.66

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.21

Np Likeness Score: 0.72

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