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

ID: ALA4852002

PubChem CID: 135196870

Max Phase: Preclinical

Molecular Formula: C16H15N5O10S2

Molecular Weight: 501.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H15N5O10S2/c17-15-18-6(3-32-15)9(20-30-2-7(22)23)11(25)19-10-12(26)21-13(10)33(29)4-5-1-8(24)31-16(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+,33+/m0/s1

Standard InChI Key:  YKKPZZWWZMJNPM-VYBLEGCUSA-N

Molfile:  

 
     RDKit          2D

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   40.9839  -12.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9839  -13.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8052  -12.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7985  -13.2576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   42.6718  -14.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4757  -14.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8088  -13.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4080  -13.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.8841  -15.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   39.4009  -12.8694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2447  -10.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2401  -11.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0310  -12.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0264  -13.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2358  -13.7163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   40.0040  -10.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9598   -9.5894    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   39.1682   -9.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   38.8771   -8.6124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.0011  -13.0466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.7969  -11.6197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   42.5133  -11.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
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  4  2  1  0
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  3 13  2  0
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  9 15  1  1
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  1 25  1  0
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 30 31  2  0
 31 22  1  0
 30 32  1  0
  8 33  1  1
  4 34  1  6
  7 35  1  6
M  CHG  2   7   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4852002

   ---

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: 501.46

Molecular Weight (Monoisotopic): 501.0260

AlogP: -2.71

#Rotatable Bonds: 7

Polar Surface Area: 233.87

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.12

CX Basic pKa: 3.59

CX LogP: -3.49

CX LogD: -9.08

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.10

Np Likeness Score: 0.09

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