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

ID: ALA4871662

PubChem CID: 135193946

Max Phase: Preclinical

Molecular Formula: C16H17N5O8S2

Molecular Weight: 471.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1[S@@+]([O-])C[C@@H]1CC(=O)O[C@@]12C(=O)O)c1csc(N)n1

Standard InChI:  InChI=1S/C16H17N5O8S2/c1-2-28-20-9(7-4-30-15(17)18-7)11(23)19-10-12(24)21-13(10)31(27)5-6-3-8(22)29-16(6,21)14(25)26/h4,6,10,13H,2-3,5H2,1H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t6-,10+,13+,16+,31-/m0/s1

Standard InChI Key:  KEYVOENCZUPOKD-OTDXEMGKSA-N

Molfile:  

 
     RDKit          2D

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   13.7849  -12.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5371  -12.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5371  -13.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3585  -12.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3517  -13.2576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7682  -12.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0633  -12.0361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7614  -13.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0581  -13.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2250  -14.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0290  -14.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3620  -13.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9612  -13.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4373  -15.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4758  -14.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6821  -14.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6809  -15.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9588  -11.8647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1673  -12.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5848  -11.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9541  -12.8694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7979  -10.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7933  -11.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5842  -12.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5796  -13.5047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5572  -10.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5130   -9.5894    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7214   -9.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2784  -10.0639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4303   -8.6124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5543  -13.0466    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.3501  -11.6197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0665  -11.2189    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
 10 11  1  0
 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
 22 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 22  1  0
 28 30  1  0
  8 31  1  1
  4 32  1  6
  7 33  1  1
M  CHG  2   7   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4871662

   ---

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: 471.47

Molecular Weight (Monoisotopic): 471.0519

AlogP: -1.77

#Rotatable Bonds: 6

Polar Surface Area: 196.57

Molecular Species: ACID

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.00

CX Basic pKa: 3.46

CX LogP: -2.55

CX LogD: -4.77

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.14

Np Likeness Score: 0.13

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