(6R,7R)-7-((2R)-2-(4-hydroxy-5-isobutyl-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxamido)-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ID: ALA4247419

PubChem CID: 145986247

Max Phase: Preclinical

Molecular Formula: C25H28N4O7S

Molecular Weight: 528.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](NC(=O)C3=C(O)C(CC(C)C)NC3=O)c3ccccc3)[C@H]2SC1

Standard InChI:  InChI=1S/C25H28N4O7S/c1-11(2)9-14-19(30)15(20(31)26-14)21(32)27-16(13-7-5-4-6-8-13)22(33)28-17-23(34)29-18(25(35)36)12(3)10-37-24(17)29/h4-8,11,14,16-17,24,30H,9-10H2,1-3H3,(H,26,31)(H,27,32)(H,28,33)(H,35,36)/t14?,16-,17-,24-/m1/s1

Standard InChI Key:  PIRVNVGJXQUSDJ-RLOMDYAQSA-N

Molfile:  

     RDKit          2D

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    4.3555  -32.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6968  -31.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318  -26.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7490  -26.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4876  -28.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0767  -28.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5308  -28.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9368  -28.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7440  -24.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9251  -24.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159  -25.1248    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709  -25.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810  -25.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780  -24.4087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7186  -30.1857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195  -31.9180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2437  -30.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3543  -32.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0614  -33.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0601  -34.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
 21  6  1  0
  6  7  1  0
  7 22  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 14 12  1  6
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  6 18  1  1
  7 19  2  0
 21 20  1  6
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 23 27  1  0
 27 28  2  0
 27 29  1  0
 24 30  1  0
 15 31  1  0
 31  1  1  0
 31 32  2  0
  5 33  1  0
  2 34  2  0
  4 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4247419

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 528.59

Molecular Weight (Monoisotopic): 528.1679

AlogP: 0.96

#Rotatable Bonds: 8

Polar Surface Area: 165.14

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.50

CX Basic pKa: ┄

CX LogP: 0.32

CX LogD: -5.28

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.25

Np Likeness Score: 0.24

References

1. Cherian PT, Cheramie MN, Marreddy RKR, Fernando DM, Hurdle JG, Lee RE..  (2018)  New β-lactam - Tetramic acid hybrids show promising antibacterial activities.,  28  (18): [PMID:30097368] [10.1016/j.bmcl.2018.07.018]

Source

Source(1):

• Scientific Literature