1-(1-(2-aminothiazol-4-yl)-2-((2R,3S)-2-((4-(guanidinomethyl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxo-1-sulfoazetidin-3-ylamino)-2-oxoethylideneaminooxy)cyclopropanecarboxylic acid

ID: ALA4217850

PubChem CID: 118379827

Max Phase: Preclinical

Molecular Formula: C17H21N11O8S2

Molecular Weight: 571.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCc1cn(C[C@@H]2[C@H](NC(=O)/C(=N\OC3(C(=O)O)CC3)c3csc(N)n3)C(=O)N2S(=O)(=O)O)nn1

Standard InChI:  InChI=1S/C17H21N11O8S2/c18-15(19)21-3-7-4-27(26-24-7)5-9-11(13(30)28(9)38(33,34)35)23-12(29)10(8-6-37-16(20)22-8)25-36-17(1-2-17)14(31)32/h4,6,9,11H,1-3,5H2,(H2,20,22)(H,23,29)(H,31,32)(H4,18,19,21)(H,33,34,35)/b25-10-/t9-,11+/m1/s1

Standard InChI Key:  CPIJWDRKSSBKSO-XAQFASHASA-N

Molfile:  

     RDKit          2D

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   32.5473  -13.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   30.0766  -11.0554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   31.4977  -11.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1750  -13.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9234  -12.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0447  -10.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8440  -11.1230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   33.4500  -10.5728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5339  -12.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3333  -12.2187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   36.6793  -12.6566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
  3  2  1  0
  1  3  1  0
  5  4  2  0
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  7  8  1  0
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  9 10  1  0
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  9 13  1  0
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  2 17  1  0
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 14 20  2  0
 14 21  1  0
 22 21  1  1
 22 23  1  0
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  5 27  1  0
 25 28  1  1
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
 31 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4217850

   1-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2R,3S)-2-[[4-[(diaminomethylideneamino)methyl]triazol-1-yl]methyl]-4-oxo-1-sulfoazetidin-3-yl]amino]-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: 571.56

Molecular Weight (Monoisotopic): 571.1016

AlogP: -3.16

#Rotatable Bonds: 11

Polar Surface Area: 294.19

Molecular Species: ZWITTERION

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -2.04

CX Basic pKa: 11.38

CX LogP: -3.59

CX LogD: -6.25

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.05

Np Likeness Score: -0.44

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