(2R,2aR,3S,4aR,7aR)-2-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[carboxymethoxyimino]-acetylamino}-1,3,6-trioxo-hexahydro-7-oxa-3-thia-7b-aza-cyclobuta[e]indene-7a-carboxylic acid

ID: ALA4849265

PubChem CID: 135196967

Max Phase: Preclinical

Molecular Formula: C15H14N6O10S2

Molecular Weight: 502.44

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H14N6O10S2/c16-14-18-9(20-32-14)7(19-30-2-5(22)23)10(25)17-8-11(26)21-12(8)33(29)3-4-1-6(24)31-15(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+,33-/m0/s1

Standard InChI Key:  KWRDULPOBLZFNN-IRCGDWLSSA-N

Molfile:  

 
     RDKit          2D

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   14.4082   -5.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1603   -4.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1603   -5.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9817   -4.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9749   -5.6346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3914   -4.8275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6865   -4.4131    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.3846   -5.6421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6814   -6.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8482   -6.8410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6522   -6.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9852   -6.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5844   -6.2222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0605   -7.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0990   -6.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3053   -6.4048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.2080   -3.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5773   -5.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4211   -3.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4165   -4.0855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2075   -4.8770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2028   -5.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4123   -6.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7821   -6.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1804   -2.7861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1363   -1.9664    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3447   -1.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9016   -2.4409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0536   -0.9894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1775   -5.4236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9733   -3.9967    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6897   -3.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
  4  2  1  0
  4  5  1  0
  4  7  1  0
  5  9  1  0
  8  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
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 11 12  1  0
 12  8  1  0
  3 13  2  0
 11 14  2  0
  9 15  1  1
 15 16  2  0
 15 17  1  0
  2 18  1  1
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 20 23  2  0
 23 24  1  0
 24  1  1  0
  1 25  1  0
 25 26  1  0
 25 27  2  0
 22 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 22  1  0
 30 32  1  0
  8 33  1  1
  4 34  1  6
  7 35  1  1
M  CHG  2   7   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4849265

   ---

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: 502.44

Molecular Weight (Monoisotopic): 502.0213

AlogP: -3.31

#Rotatable Bonds: 7

Polar Surface Area: 246.76

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.11

CX Basic pKa: 0.07

CX LogP: -1.94

CX LogD: -9.06

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.09

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