2-((S)-4-((Z)-2-(2-aminothiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetamido)-3-oxoisoxazolidin-2-yl)-5-oxotetrahydrofuran-2-carboxylic acid

ID: ALA3265220

PubChem CID: 14095866

Max Phase: Preclinical

Molecular Formula: C17H19N5O10S

Molecular Weight: 485.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O/N=C(\C(=O)N[C@H]1CON(C2(C(=O)O)CCC(=O)O2)C1=O)c1csc(N)n1)C(=O)O

Standard InChI:  InChI=1S/C17H19N5O10S/c1-16(2,13(26)27)32-21-10(8-6-33-15(18)20-8)11(24)19-7-5-30-22(12(7)25)17(14(28)29)4-3-9(23)31-17/h6-7H,3-5H2,1-2H3,(H2,18,20)(H,19,24)(H,26,27)(H,28,29)/b21-10-/t7-,17?/m0/s1

Standard InChI Key:  MXXZEBJOWBKAOL-NXDUIBFMSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   12.8068   -1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5167   -1.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5156   -1.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5492   -4.8495    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3664   -4.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6207   -4.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9578   -3.5907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2990   -4.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5217   -3.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3983   -3.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0048   -4.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7823   -4.1176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8338   -5.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5693   -3.0223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3468   -2.7708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3321   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7921   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6934   -1.1769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3889   -4.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2996   -5.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0457   -5.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5933   -5.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1856   -4.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5906   -5.8823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2166   -6.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6690   -7.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0766   -7.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8762   -7.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9626   -6.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7432   -8.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0045   -6.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5782   -6.9800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2205   -5.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  4  1  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 10 14  2  0
 14 15  1  0
 15  2  1  0
  2 16  1  0
 16 17  1  0
 16 18  2  0
 19 12  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 20 24  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 21 25  1  0
 27 30  2  0
 25 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3265220

   2-[(4S)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-oxo-1,2-oxazolidin-2-yl]-5-oxooxolane-2-carboxylic 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: 485.43

Molecular Weight (Monoisotopic): 485.0853

AlogP: -1.31

#Rotatable Bonds: 8

Polar Surface Area: 220.04

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.20

CX Basic pKa: 3.92

CX LogP: -1.24

CX LogD: -6.81

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.19

Np Likeness Score: 0.29

References

1. Starr J, Brown MF, Aschenbrenner L, Caspers N, Che Y, Gerstenberger BS, Huband M, Knafels JD, Lemmon MM, Li C, McCurdy SP, McElroy E, Rauckhorst MR, Tomaras AP, Young JA, Zaniewski RP, Shanmugasundaram V, Han S..  (2014)  Siderophore receptor-mediated uptake of lactivicin analogues in gram-negative bacteria.,  57  (9): [PMID:24694215] [10.1021/jm500219c]

2. Sato J, Kusano H, Aoki T, Shibuya S, Yokoo K, Komano K, Oguma T, Matsumoto S, Sato T, Yasuo K, Yamawaki K..  (2021)  A novel tricyclic β-lactam exhibiting potent antibacterial activities against carbapenem-resistant Enterobacterales: Synthesis and structure-activity-relationships.,  46  [PMID:34450571] [10.1016/j.bmc.2021.116343]

Source

Source(1):

• Scientific Literature