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

ID: ALA3326182

PubChem CID: 118711432

Max Phase: Preclinical

Molecular Formula: C19H15N3O7

Molecular Weight: 397.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C19H15N3O7/c1-28-13-5-2-11(3-6-13)14-8-9-29-17(14)19(25)21-20-18(24)12-4-7-16(23)15(10-12)22(26)27/h2-10,23H,1H3,(H,20,24)(H,21,25)

Standard InChI Key:  WLWGUKLSXBGTKX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   14.7504   -7.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0041   -7.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4568   -7.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8649   -8.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6643   -8.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2696   -8.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0976   -9.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7037  -10.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4820   -9.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6508   -9.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0434   -8.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5320   -9.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7192   -9.2206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0119   -9.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3863   -9.9669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5735  -10.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2406  -10.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0937   -9.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4274  -10.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0945  -11.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5745  -12.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3912  -12.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7204  -11.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2426  -13.0326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2843  -11.7098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9522  -12.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8026  -11.0531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0896  -10.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9202  -11.2069    0.0000 C   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
 28 29  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326182

   ---

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: 397.34

Molecular Weight (Monoisotopic): 397.0910

AlogP: 2.64

#Rotatable Bonds: 5

Polar Surface Area: 143.94

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.75

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 0.47

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.03

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