1-(2-((2R,3S)-2-(((R)-5-(aminomethyl)-2-oxooxazolidin-3-yl)methyl)-4-oxo-1-sulfoazetidin-3-ylamino)-1-(2-aminothiazol-4-yl)-2-oxoethylideneaminooxy)cyclopropanecarboxylic acid

ID: ALA4213450

PubChem CID: 118379578

Max Phase: Preclinical

Molecular Formula: C17H21N7O10S2

Molecular Weight: 547.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC[C@@H]1CN(C[C@@H]2[C@H](NC(=O)/C(=N\OC3(C(=O)O)CC3)c3csc(N)n3)C(=O)N2S(=O)(=O)O)C(=O)O1

Standard InChI:  InChI=1S/C17H21N7O10S2/c18-3-7-4-23(16(29)33-7)5-9-11(13(26)24(9)36(30,31)32)21-12(25)10(8-6-35-15(19)20-8)22-34-17(1-2-17)14(27)28/h6-7,9,11H,1-5,18H2,(H2,19,20)(H,21,25)(H,27,28)(H,30,31,32)/b22-10-/t7-,9-,11+/m1/s1

Standard InChI Key:  USNQSQVXOXARQK-VARFGCAOSA-N

Molfile:  

     RDKit          2D

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    6.9626  -11.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6990  -15.7619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6910  -14.5098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6494  -13.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3266  -15.1575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6814  -14.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4808  -14.3543    0.0000 N   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
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  8  9  2  0
  9 10  1  0
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  9 13  1  0
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  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  1
 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
 31 35  1  6
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213450

   1-[(Z)-[2-[[(2R,3S)-2-[[(5R)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-1-(2-amino-1,3-thiazol-4-yl)-2-oxoethylidene]amino]oxycyclopropane-1-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: 547.53

Molecular Weight (Monoisotopic): 547.0791

AlogP: -2.66

#Rotatable Bonds: 10

Polar Surface Area: 257.14

Molecular Species: ZWITTERION

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -2.01

CX Basic pKa: 8.82

CX LogP: -3.97

CX LogD: -6.65

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.09

Np Likeness Score: 0.02

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