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

ID: ALA4866303

PubChem CID: 145179276

Max Phase: Preclinical

Molecular Formula: C16H14ClN5O9S2

Molecular Weight: 519.90

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)c(Cl)s1

Standard InChI:  InChI=1S/C16H14ClN5O9S2/c17-10-7(20-15(18)33-10)8(21-30-2-5(23)24)11(26)19-9-12(27)22-13(9)32-3-4-1-6(25)31-16(4,22)14(28)29/h4,9,13H,1-3H2,(H2,18,20)(H,19,26)(H,23,24)(H,28,29)/b21-8-/t4-,9+,13+,16+/m0/s1

Standard InChI Key:  ODTKLVLHXPPREX-JQKXTGDSSA-N

Molfile:  

 
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   25.6029  -13.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3534  -12.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3534  -13.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1747  -12.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1680  -13.5919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.5844  -12.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8795  -12.3704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.5777  -13.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8744  -14.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0413  -14.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8452  -14.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1783  -14.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7774  -14.1795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2535  -15.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2921  -14.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4983  -14.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4972  -15.3766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7750  -12.1990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9835  -12.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4010  -11.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7704  -13.2037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6142  -11.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6095  -12.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4005  -12.8343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3958  -13.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6053  -14.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9752  -14.4199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3735  -10.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3293   -9.9237    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.5377   -9.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0947  -10.3982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2466   -8.9467    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3706  -13.3809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.1664  -11.9540    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.0600  -11.1866    0.0000 Cl  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
 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
 28 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866303

   ---

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: 519.90

Molecular Weight (Monoisotopic): 518.9921

AlogP: -1.07

#Rotatable Bonds: 7

Polar Surface Area: 210.81

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.87

CX Basic pKa: 2.57

CX LogP: -0.23

CX LogD: -6.52

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: 0.02

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