3-(4-fluorophenyl)-N'-(4-hydroxy-3-nitrobenzoyl)furan-2-carbohydrazide

ID: ALA3326183

PubChem CID: 118711433

Max Phase: Preclinical

Molecular Formula: C18H12FN3O6

Molecular Weight: 385.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NNC(=O)c1occc1-c1ccc(F)cc1)c1ccc(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H12FN3O6/c19-12-4-1-10(2-5-12)13-7-8-28-16(13)18(25)21-20-17(24)11-3-6-15(23)14(9-11)22(26)27/h1-9,23H,(H,20,24)(H,21,25)

Standard InChI Key:  CPDZXQLZWXDRGY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    7.1357   -3.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3894   -3.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8421   -3.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2502   -4.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0496   -4.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6549   -4.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4828   -5.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0889   -6.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8673   -5.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0361   -5.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4286   -4.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173   -5.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1045   -5.1635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3971   -5.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7716   -5.9098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9588   -5.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259   -6.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789   -5.3332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8127   -6.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4798   -7.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -8.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7765   -8.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -7.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6279   -8.9755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6696   -7.6527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -8.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879   -6.9960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4749   -6.3504    0.0000 F   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  2  0
  5  1  1  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
  5  6  1  0
  4 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 21 24  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
  9 28  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326183

   ---

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: 385.31

Molecular Weight (Monoisotopic): 385.0710

AlogP: 2.77

#Rotatable Bonds: 4

Polar Surface Area: 134.71

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.75

CX Basic pKa: ┄

CX LogP: 2.58

CX LogD: 0.76

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.34

References

1. Hasegawa F, Niidome K, Migihashi C, Murata M, Negoro T, Matsumoto T, Kato K, Fujii A..  (2014)  Discovery of furan-2-carbohydrazides as orally active glucagon receptor antagonists.,  24  (17): [PMID:25127101] [10.1016/j.bmcl.2014.07.025]

Source

Source(1):

• Scientific Literature