3-(7-(4-bromo-2-fluorobenzyloxy)-4,8-dimethyl-2-oxo-2H-chromen-3-yl)propanoic acid

ID: ALA540680

Cas Number: 701931-60-4

PubChem CID: 1296013

Max Phase: Preclinical

Molecular Formula: C21H18BrFO5

Molecular Weight: 449.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CCC(=O)O)c(=O)oc2c(C)c(OCc3ccc(Br)cc3F)ccc12

Standard InChI:  InChI=1S/C21H18BrFO5/c1-11-15-5-7-18(27-10-13-3-4-14(22)9-17(13)23)12(2)20(15)28-21(26)16(11)6-8-19(24)25/h3-5,7,9H,6,8,10H2,1-2H3,(H,24,25)

Standard InChI Key:  IMVNNUIMTGKSKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    0.9487   -1.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3777   -0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632   -1.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3777   -1.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8066   -0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5211   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5211    0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356    0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500    0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3790    0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3790   -0.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935   -0.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0935    0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645    1.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8079    0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5224    0.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2369    0.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5224    1.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -1.8906    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.6632    0.5844    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -1.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 13 14  1  0
  4  7  1  0
 14 15  1  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
 18 13  1  0
  8  9  1  0
 17 19  2  0
  4  6  2  0
 16 20  1  0
  9 10  2  0
 15 21  1  0
  1  2  1  0
 20 22  1  0
 10 11  1  0
 22 23  1  0
 11 14  2  0
 23 24  2  0
  5  1  2  0
 23 25  1  0
 13 12  2  0
  1 26  1  0
 12  9  1  0
  3 27  1  0
  5  6  1  0
 12 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA540680

   3-{7-[(4-bromo-2-fluorobenzyl)oxy]-4,8-dimethyl-2-oxo-2H-chromen-3-yl}propanoic acid

Molecule Features

Natural Product: Yes

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: 449.27

Molecular Weight (Monoisotopic): 448.0322

AlogP: 4.91

#Rotatable Bonds: 6

Polar Surface Area: 76.74

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.80

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 1.78

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.70

References

1. Aiello D, Barnes MH, Biswas EE, Biswas SB, Gu S, Williams JD, Bowlin TL, Moir DT..  (2009)  Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases.,  17  (13): [PMID:19477652] [10.1016/j.bmc.2009.05.014]

Source

Source(1):

• Scientific Literature