1-(1-(2-aminothiazol-4-yl)-2-oxo-2-((3S,4S)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3-ylamino)ethylideneaminooxy)cyclopropanecarboxylic acid

ID: ALA4218376

PubChem CID: 145970072

Max Phase: Preclinical

Molecular Formula: C16H18N6O10S2

Molecular Weight: 518.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(/C(=N/OC2(C(=O)O)CC2)C(=O)N[C@@H]2C(=O)N(S(=O)(=O)O)[C@H]2CN2CCOC2=O)cs1

Standard InChI:  InChI=1S/C16H18N6O10S2/c17-14-18-7(6-33-14)9(20-32-16(1-2-16)13(25)26)11(23)19-10-8(5-21-3-4-31-15(21)27)22(12(10)24)34(28,29)30/h6,8,10H,1-5H2,(H2,17,18)(H,19,23)(H,25,26)(H,28,29,30)/b20-9-/t8-,10-/m0/s1

Standard InChI Key:  FWTGYTRQUBRVDW-FKKDBYOTSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    6.3270  -17.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1195  -18.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091  -17.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8558  -22.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4514  -22.0188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0424  -22.7219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1520  -20.8838    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9692  -20.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2235  -20.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5606  -19.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018  -20.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245  -19.8549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0011  -19.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6076  -20.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1721  -19.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9496  -18.8051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8982  -17.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0692  -16.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5047  -18.3022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4366  -21.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3851  -20.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917  -20.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0317  -21.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8478  -21.4724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8062  -20.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4835  -22.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2319  -21.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3532  -20.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1525  -20.2194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4789  -20.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2917  -20.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4619  -20.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7543  -19.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6666  -18.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  5  4  2  0
  6  5  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  2  1  0
  2 17  1  0
 17 18  1  0
 17 19  2  0
 14 20  2  0
 14 21  1  0
 22 21  1  1
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 22  1  0
 23 26  2  0
 24  5  1  0
  5 27  1  0
 25 28  1  6
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 29  1  0
 33 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4218376

   ---

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: 518.49

Molecular Weight (Monoisotopic): 518.0526

AlogP: -1.99

#Rotatable Bonds: 9

Polar Surface Area: 231.12

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.48

CX Basic pKa: 3.87

CX LogP: -4.05

CX LogD: -7.12

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -0.28

References

1. Reck F, Bermingham A, Blais J, Capka V, Cariaga T, Casarez A, Colvin R, Dean CR, Fekete A, Gong W, Growcott E, Guo H, Jones AK, Li C, Li F, Lin X, Lindvall M, Lopez S, McKenney D, Metzger L, Moser HE, Prathapam R, Rasper D, Rudewicz P, Sethuraman V, Shen X, Shaul J, Simmons RL, Tashiro K, Tang D, Tjandra M, Turner N, Uehara T, Vitt C, Whitebread S, Yifru A, Zang X, Zhu Q..  (2018)  Optimization of novel monobactams with activity against carbapenem-resistant Enterobacteriaceae - Identification of LYS228.,  28  (4): [PMID:29336873] [10.1016/j.bmcl.2018.01.006]

Source

Source(1):

• Scientific Literature