2-(3-(4-bromobenzyloxy)benzoyl)-3-hydroxycyclohex-2-en-1-one

ID: ALA4554387

PubChem CID: 155555934

Max Phase: Preclinical

Molecular Formula: C20H17BrO4

Molecular Weight: 401.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1cccc(OCc2ccc(Br)cc2)c1

Standard InChI:  InChI=1S/C20H17BrO4/c21-15-9-7-13(8-10-15)12-25-16-4-1-3-14(11-16)20(24)19-17(22)5-2-6-18(19)23/h1,3-4,7-11,22H,2,5-6,12H2

Standard InChI Key:  XZKNWZIKSNAUIS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   21.9513   -3.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9502   -4.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6582   -4.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3679   -4.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3650   -3.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6564   -3.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2435   -3.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2433   -2.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5359   -3.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8262   -3.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1207   -3.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1167   -4.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8244   -4.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5360   -4.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8296   -2.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2429   -4.8904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0712   -3.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7805   -3.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4866   -3.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1943   -3.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9000   -3.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8973   -2.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1831   -2.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4803   -2.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6029   -2.0174    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  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 14 16  2  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554387

   ---

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: 401.26

Molecular Weight (Monoisotopic): 400.0310

AlogP: 4.78

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.50

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 1.52

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.23

References

1. Ndikuryayo F, Kang WM, Wu FX, Yang WC, Yang GF..  (2019)  Hydrophobicity-oriented drug design (HODD) of new human 4-hydroxyphenylpyruvate dioxygenase inhibitors.,  166  [PMID:30684868] [10.1016/j.ejmech.2019.01.032]

Source

Source(1):

• Scientific Literature