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

ID: ALA4237839

PubChem CID: 145984190

Max Phase: Preclinical

Molecular Formula: C28H33N5O8S

Molecular Weight: 599.67

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H33N5O8S/c1-13(2)11-16-22(35)18(24(37)30-16)23(36)29-10-9-17(34)31-19(15-7-5-4-6-8-15)25(38)32-20-26(39)33-21(28(40)41)14(3)12-42-27(20)33/h4-8,13,16,19-20,27,35H,9-12H2,1-3H3,(H,29,36)(H,30,37)(H,31,34)(H,32,38)(H,40,41)/t16?,19-,20-,27-/m1/s1

Standard InChI Key:  YDKUWOLIEUTFEY-NPTINWMTSA-N

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
    9.9821  -33.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8071  -33.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0639  -33.8590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3946  -34.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7296  -33.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9449  -34.1136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2913  -32.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3934  -35.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1071  -35.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1059  -36.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8223  -35.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9567  -25.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7817  -25.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4892  -27.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0743  -28.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868  -28.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3140  -28.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7269  -28.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3120  -27.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5518  -28.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9669  -28.7881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9618  -27.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7868  -27.3563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5468  -26.6463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3651  -26.5137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2374  -25.5120    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9550  -25.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7817  -25.1054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1902  -24.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7766  -23.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9499  -23.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5368  -24.3978    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0152  -24.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4292  -25.1038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4262  -23.6749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1876  -22.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5569  -29.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7319  -29.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9719  -30.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5620  -30.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9771  -31.6460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5671  -32.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7421  -32.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  5  6  1  0
  2  7  2  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 27 12  1  0
 12 13  1  0
 13 28  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 20 18  1  6
 20 21  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 12 24  1  1
 13 25  2  0
 27 26  1  6
 27 28  1  0
 27 32  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 29 33  1  0
 33 34  2  0
 33 35  1  0
 30 36  1  0
 21 37  1  0
 37 38  2  0
 37 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42  1  1  0
 42 43  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4237839

   ---

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: 599.67

Molecular Weight (Monoisotopic): 599.2050

AlogP: 0.47

#Rotatable Bonds: 11

Polar Surface Area: 194.24

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.50

CX Basic pKa: ┄

CX LogP: -0.54

CX LogD: -6.03

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.15

Np Likeness Score: -0.01

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