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

ID: ALA4863878

PubChem CID: 15117618

Max Phase: Preclinical

Molecular Formula: C16H15N5O9S2

Molecular Weight: 485.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H15N5O9S2/c17-15-18-6(4-32-15)9(20-29-2-7(22)23)11(25)19-10-12(26)21-13(10)31-3-5-1-8(24)30-16(5,21)14(27)28/h4-5,10,13H,1-3H2,(H2,17,18)(H,19,25)(H,22,23)(H,27,28)/b20-9-/t5-,10+,13+,16+/m0/s1

Standard InChI Key:  BJVOKJXLICGBLJ-OGELVBSKSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   15.1858  -20.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9363  -19.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9363  -20.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7576  -19.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7509  -20.5834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1673  -19.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4624  -19.3619    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.1606  -20.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4573  -20.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6242  -21.7898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4281  -21.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7611  -21.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3603  -21.1710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8364  -22.5891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8749  -21.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0812  -21.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0801  -22.3682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3579  -19.1905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5664  -19.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9839  -18.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3532  -20.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1971  -18.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1924  -19.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9834  -19.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9787  -20.8305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1882  -21.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5580  -21.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9563  -17.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9122  -16.9152    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.1206  -16.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6775  -17.3897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8295  -15.9383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9534  -20.3724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7493  -18.9455    0.0000 H   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
M  END

Alternative Forms

1. Parent:

   

   ALA4863878

   (1R,4R,5R,8R)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3,10-dioxo-11-oxa-6-thia-2-azatricyclo[6.3.0.02,5]undecane-1-carboxylic acid

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: 485.46

Molecular Weight (Monoisotopic): 485.0311

AlogP: -1.73

#Rotatable Bonds: 7

Polar Surface Area: 210.81

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.25

CX Basic pKa: 3.91

CX LogP: -1.66

CX LogD: -7.27

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.15

Np Likeness Score: 0.10

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