Penicillin V methyl ester

ID: ALA3114798

Cas Number: 2315-05-1

PubChem CID: 638030

Max Phase: Preclinical

Molecular Formula: C17H20N2O5S

Molecular Weight: 364.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@H]1N2C(=O)[C@@H](NC(=O)COc3ccccc3)[C@H]2SC1(C)C

Standard InChI:  InChI=1S/C17H20N2O5S/c1-17(2)13(16(22)23-3)19-14(21)12(15(19)25-17)18-11(20)9-24-10-7-5-4-6-8-10/h4-8,12-13,15H,9H2,1-3H3,(H,18,20)/t12-,13+,15-/m1/s1

Standard InChI Key:  JYVSRPXYJNDSQP-VNHYZAJKSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   28.7929   -4.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7929   -3.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9686   -4.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9686   -3.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5798   -4.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5673   -3.3472    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.0627   -4.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3816   -3.0225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0039   -5.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6571   -3.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3816   -5.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8325   -5.3803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6405   -4.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2333   -3.3847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9578   -2.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5993   -6.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7788   -4.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6414   -3.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5214   -2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8095   -3.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5547   -2.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8470   -1.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1059   -2.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1225   -2.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7804   -2.7810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.0302   -6.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  1  1  0
  6  2  1  0
  7  5  1  0
  4  8  1  1
  5  9  1  6
 10  8  1  0
 11  3  2  0
 12  9  2  0
 13 10  2  0
 14 15  1  0
 15 10  1  0
 16  9  1  0
 17  7  1  0
 18  7  1  0
 19 14  1  0
 20 19  1  0
 21 19  2  0
 22 21  1  0
 23 20  2  0
 24 22  2  0
  2 25  1  6
  7  6  1  0
  2  4  1  0
 23 24  1  0
 16 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3114798

   4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(phenoxyacetamido)-, methyl ester

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: 364.42

Molecular Weight (Monoisotopic): 364.1093

AlogP: 0.79

#Rotatable Bonds: 5

Polar Surface Area: 84.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.73

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.07

References

1. Dave K, Palzkill T, Pratt RF..  (2014)  Neutral β-Lactams Inactivate High Molecular Mass Penicillin-Binding Proteins of Class B1, Including PBP2a of MRSA.,  5  (2): [PMID:24900789] [10.1021/ml400408c]

Source

Source(1):

• Scientific Literature