(2R,2aR,4aR,7aR)-2-{2-(2-Amino-thiazol-4-yl)-2-[carboxymethoxyimino]-acetylamino}-1,3,3,6-tetraoxo-octahydro-7-oxa-3lambda(6)-thia-7b-aza-cyclobuta[e]indene-7a-carboxylic acid

ID: ALA4847598

PubChem CID: 135196775

Max Phase: Preclinical

Molecular Formula: C16H15N5O11S2

Molecular Weight: 517.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(/C(=N/OCC(=O)O)C(=O)N[C@@H]2C(=O)N3[C@@H]2S(=O)(=O)C[C@@H]2CC(=O)O[C@@]23C(=O)O)cs1

Standard InChI:  InChI=1S/C16H15N5O11S2/c17-15-18-6(3-33-15)9(20-31-2-7(22)23)11(25)19-10-12(26)21-13(10)34(29,30)4-5-1-8(24)32-16(5,21)14(27)28/h3,5,10,13H,1-2,4H2,(H2,17,18)(H,19,25)(H,22,23)(H,27,28)/b20-9-/t5-,10+,13+,16+/m0/s1

Standard InChI Key:  VDPURUJYIPVCQC-OGELVBSKSA-N

Molfile:  

 
     RDKit          2D

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   42.9727  -19.8726    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   43.3811  -19.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6998  -20.5447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4503  -20.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4503  -21.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2716  -20.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2649  -21.0952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   43.1382  -22.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.9421  -22.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2752  -21.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8744  -21.6828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   39.4979  -19.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8673  -20.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.7111  -18.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7064  -19.5461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4974  -20.3376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.4927  -21.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7022  -21.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.0721  -21.9232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4704  -18.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4262  -17.4270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.6346  -17.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1916  -17.9015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3435  -16.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.4675  -20.8842    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   42.2633  -19.4573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  5  6  1  0
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  9  2  1  0
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 13 16  2  0
 11 17  1  1
 17 18  2  0
 17 19  1  0
  5 20  1  1
 20 21  1  0
 21 22  1  0
 21 23  2  0
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 25 26  1  0
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  4 27  1  0
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 32 34  1  0
 10 35  1  1
  7 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4847598

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 517.45

Molecular Weight (Monoisotopic): 517.0209

AlogP: -3.04

#Rotatable Bonds: 7

Polar Surface Area: 244.95

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.08

CX Basic pKa: 3.59

CX LogP: -3.40

CX LogD: -8.97

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.12

Np Likeness Score: -0.16

References

1. 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