N'-(4-hydroxy-3-nitrobenzoyl)-3,4-diphenylfuran-2-carbohydrazide

ID: ALA3326175

PubChem CID: 11532336

Max Phase: Preclinical

Molecular Formula: C24H17N3O6

Molecular Weight: 443.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NNC(=O)c1occ(-c2ccccc2)c1-c1ccccc1)c1ccc(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C24H17N3O6/c28-20-12-11-17(13-19(20)27(31)32)23(29)25-26-24(30)22-21(16-9-5-2-6-10-16)18(14-33-22)15-7-3-1-4-8-15/h1-14,28H,(H,25,29)(H,26,30)

Standard InChI Key:  HWMNYSSRAMHIFI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.1851  -26.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8932  -26.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029  -26.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6000  -25.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8914  -24.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4775  -26.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7312  -26.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1839  -26.6831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5920  -27.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3914  -27.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9967  -27.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8247  -28.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4308  -29.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4463  -28.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7390  -28.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1134  -28.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3006  -29.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9677  -29.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8208  -28.3920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1545  -29.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216  -30.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3016  -31.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1183  -31.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4475  -30.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9697  -32.0343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0041  -30.7120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6708  -31.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5246  -30.0503    0.0000 O   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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  2  7  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
 11 12  1  0
 10 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 23  1  0
 27 30  1  0
 31 32  2  0
 31 33  1  0
 26 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326175

   3,4-Diphenyl-2-furancarboxylic acid 2-(4-hydroxy-3-nitrobenzoyl)hydrazide

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: 443.42

Molecular Weight (Monoisotopic): 443.1117

AlogP: 4.30

#Rotatable Bonds: 5

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: 5.76

CX Basic pKa: ┄

CX LogP: 4.08

CX LogD: 2.39

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.69

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