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

ID: ALA4875678

PubChem CID: 15117610

Max Phase: Preclinical

Molecular Formula: C18H19N5O9S2

Molecular Weight: 513.51

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H19N5O9S2/c1-17(2,14(27)28)32-22-9(7-5-34-16(19)20-7)11(25)21-10-12(26)23-13(10)33-4-6-3-8(24)31-18(6,23)15(29)30/h5-6,10,13H,3-4H2,1-2H3,(H2,19,20)(H,21,25)(H,27,28)(H,29,30)/b22-9-/t6-,10+,13+,18+/m0/s1

Standard InChI Key:  DLGMVQXWJRCHMV-BFAIENCSSA-N

Molfile:  

 
     RDKit          2D

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    3.9015  -11.9190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3866  -10.2744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5386   -8.8229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6626  -13.2571    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4584  -11.8302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
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 11 17  1  1
 17 18  2  0
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  4 20  1  1
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  2 27  1  0
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 10 35  1  1
  6 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4875678

   (1R,4R,5R,8R)-4-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)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: 513.51

Molecular Weight (Monoisotopic): 513.0624

AlogP: -0.95

#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: 2.26

CX Basic pKa: 3.92

CX LogP: -0.75

CX LogD: -6.25

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 0.45

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