(R)-3-(4-(4-Bromophenyl)butyl)-4-hydroxy-5-methyl-5-((E)-2-methylbuta-1,3-dienyl)thiophen-2(5H)-one

ID: ALA4458874

PubChem CID: 136624741

Max Phase: Preclinical

Molecular Formula: C20H23BrO2S

Molecular Weight: 407.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/[C@@]1(C)SC(=O)C(CCCCc2ccc(Br)cc2)=C1O

Standard InChI:  InChI=1S/C20H23BrO2S/c1-4-14(2)13-20(3)18(22)17(19(23)24-20)8-6-5-7-15-9-11-16(21)12-10-15/h4,9-13,22H,1,5-8H2,2-3H3/b14-13+/t20-/m1/s1

Standard InChI Key:  CFZCXAQCNBNYJY-FBRRREGBSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   11.7717   -2.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5992   -2.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8442   -1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1667   -1.4414    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5055   -1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6246   -1.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0780   -1.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7546   -2.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0770   -1.8118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3260   -2.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1500   -0.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6526   -1.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2974   -3.3971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0938   -3.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7703   -4.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2650   -4.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9414   -5.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4361   -6.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1098   -6.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6037   -7.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4229   -7.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7457   -6.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2498   -6.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9184   -8.1788    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  3  6  2  0
  5  7  1  6
  5  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 10 12  2  0
  1 13  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4458874

   ---

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: 407.37

Molecular Weight (Monoisotopic): 406.0602

AlogP: 6.14

#Rotatable Bonds: 7

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 6.23

CX LogD: 5.53

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.44

Np Likeness Score: 1.05

References

1. Bommineni GR, Kapilashrami K, Cummings JE, Lu Y, Knudson SE, Gu C, Walker SG, Slayden RA, Tonge PJ..  (2016)  Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity.,  59  (11): [PMID:27187871] [10.1021/acs.jmedchem.6b00236]

Source

Source(1):

• Scientific Literature