(6R,7R)-Methyl 3-methyl-8-oxo-7-(3-phenylpropanamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

ID: ALA4483411

PubChem CID: 155540737

Max Phase: Preclinical

Molecular Formula: C18H20N2O4S

Molecular Weight: 360.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(C)CS[C@@H]2[C@H](NC(=O)CCc3ccccc3)C(=O)N12

Standard InChI:  InChI=1S/C18H20N2O4S/c1-11-10-25-17-14(16(22)20(17)15(11)18(23)24-2)19-13(21)9-8-12-6-4-3-5-7-12/h3-7,14,17H,8-10H2,1-2H3,(H,19,21)/t14-,17-/m1/s1

Standard InChI Key:  DBGCGDTYXPKCSE-RHSMWYFYSA-N

Molfile:  

 
     RDKit          2D

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   34.4128  -10.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1181  -10.7679    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.1181   -9.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8234   -9.5463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8244  -10.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6461  -10.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6451   -9.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7039   -9.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1181   -8.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8258   -7.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2247  -10.9441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0138  -10.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2243   -9.9420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2222   -8.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8202  -11.1848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.5923  -11.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4104   -7.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3814  -11.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9600  -11.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7468  -12.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3246  -13.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1146  -12.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3237  -12.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7444  -11.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4104   -7.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  4  1  0
  5  6  1  0
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  7  8  1  0
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  7 12  1  1
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  8 15  2  0
  6 16  1  6
 13 17  1  0
 10 18  1  0
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 20 21  2  0
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 23 24  1  0
 24 25  2  0
 25 20  1  0
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483411

   ---

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: 360.44

Molecular Weight (Monoisotopic): 360.1144

AlogP: 1.47

#Rotatable Bonds: 5

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.12

CX Basic pKa: ┄

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.64

Np Likeness Score: -0.18

References

1. Gold B, Smith R, Nguyen Q, Roberts J, Ling Y, Lopez Quezada L, Somersan S, Warrier T, Little D, Pingle M, Zhang D, Ballinger E, Zimmerman M, Dartois V, Hanson P, Mitscher LA, Porubsky P, Rogers S, Schoenen FJ, Nathan C, Aubé J..  (2016)  Novel Cephalosporins Selectively Active on Nonreplicating Mycobacterium tuberculosis.,  59  (13): [PMID:27144688] [10.1021/acs.jmedchem.5b01833]

Source

Source(1):

• Scientific Literature