(3aR,5aR,6R,8aR)-6-(2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(carboxymethoxyimino)acetamido)-2,7-dioxooctahydroazeto[2,1-b]furo[2,3-d][1,3]thiazine-8a-carboxylic acid

ID: ALA4873728

PubChem CID: 164621212

Max Phase: Preclinical

Molecular Formula: C15H14N6O9S2

Molecular Weight: 486.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1nc(/C(=N/OCC(=O)O)C(=O)N[C@@H]2C(=O)N3[C@@H]2SC[C@@H]2CC(=O)O[C@@]23C(=O)O)ns1

Standard InChI:  InChI=1S/C15H14N6O9S2/c16-14-18-9(20-32-14)7(19-29-2-5(22)23)10(25)17-8-11(26)21-12(8)31-3-4-1-6(24)30-15(4,21)13(27)28/h4,8,12H,1-3H2,(H,17,25)(H,22,23)(H,27,28)(H2,16,18,20)/b19-7-/t4-,8+,12+,15+/m0/s1

Standard InChI Key:  KAJHZGSVKMMXEA-KFQVEHGUSA-N

Molfile:  

 
     RDKit          2D

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   29.7290  -20.2972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.7761  -20.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7714  -21.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.3508  -21.9397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   28.7049  -17.4435    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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   32.7461  -20.9007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.5420  -19.4738    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 15  1  1
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  2 18  1  1
 18 19  1  0
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  1 25  1  0
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 31 22  1  0
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  8 33  1  1
  4 34  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4873728

   ---

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: 486.44

Molecular Weight (Monoisotopic): 486.0264

AlogP: -2.33

#Rotatable Bonds: 7

Polar Surface Area: 223.70

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.31

CX Basic pKa: 0.07

CX LogP: -0.35

CX LogD: -7.44

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.14

Np Likeness Score: 0.07

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