3,4-Dibromo-5-(5-(4-(p-tolyloxy)phenyl)oxazol-2-yl)benzene-1,2-diol

ID: ALA4513341

PubChem CID: 155538861

Max Phase: Preclinical

Molecular Formula: C22H15Br2NO4

Molecular Weight: 517.17

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(Oc2ccc(-c3cnc(-c4cc(O)c(O)c(Br)c4Br)o3)cc2)cc1

Standard InChI:  InChI=1S/C22H15Br2NO4/c1-12-2-6-14(7-3-12)28-15-8-4-13(5-9-15)18-11-25-22(29-18)16-10-17(26)21(27)20(24)19(16)23/h2-11,26-27H,1H3

Standard InChI Key:  RWNXHFJDYZGYKR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   30.8758  -19.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6930  -19.7860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9473  -19.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2844  -18.5271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6256  -19.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7211  -18.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3276  -19.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1045  -19.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2761  -18.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6647  -17.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8901  -17.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8505  -18.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6813  -17.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9048  -17.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2969  -18.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4706  -19.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2468  -19.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8329  -16.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0533  -18.0026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7108  -19.6029    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   27.5192  -18.0030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3479  -17.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9562  -16.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7854  -15.8608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0070  -15.6089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3993  -16.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5733  -16.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1557  -20.1047    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   26.8347  -14.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  5 12  1  0
 10 18  1  0
  9 19  1  0
  8 20  1  0
 15 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  7 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513341

   ---

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: 517.17

Molecular Weight (Monoisotopic): 514.9368

AlogP: 7.05

#Rotatable Bonds: 4

Polar Surface Area: 75.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.87

CX Basic pKa: 0.50

CX LogP: 6.45

CX LogD: 5.82

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.28

Np Likeness Score: -0.09

References

1. Li X, Xu Q, Li C, Luo J, Li X, Wang L, Jiang B, Shi D..  (2019)  Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors.,  166  [PMID:30711829] [10.1016/j.ejmech.2019.01.057]

Source

Source(1):

• Scientific Literature