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

ID: ALA4861857

PubChem CID: 135196801

Max Phase: Preclinical

Molecular Formula: C17H17N5O9S2

Molecular Weight: 499.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](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/C17H17N5O9S2/c1-5(14(26)27)31-21-9(7-4-33-16(18)19-7)11(24)20-10-12(25)22-13(10)32-3-6-2-8(23)30-17(6,22)15(28)29/h4-6,10,13H,2-3H2,1H3,(H2,18,19)(H,20,24)(H,26,27)(H,28,29)/b21-9-/t5-,6+,10-,13-,17-/m1/s1

Standard InChI Key:  XVAXYUIMQCBLNZ-VRYCXASFSA-N

Molfile:  

 
     RDKit          2D

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   18.6845  -12.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.7269  -13.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.7046  -10.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.5777   -8.4473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7017  -12.8815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4975  -11.4546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3562  -11.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 15  1  1
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  2 18  1  1
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  1 25  1  0
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  8 33  1  1
  4 34  1  6
  1 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4861857

   ---

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: 499.48

Molecular Weight (Monoisotopic): 499.0468

AlogP: -1.34

#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: 2.26

CX Basic pKa: 3.92

CX LogP: -1.20

CX LogD: -6.69

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.15

Np Likeness Score: 0.12

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