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

ID: ALA3326184

PubChem CID: 118711434

Max Phase: Preclinical

Molecular Formula: C18H12ClN3O6

Molecular Weight: 401.76

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H12ClN3O6/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:  CNYARJOQCNHFTG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   14.1602   -9.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4139   -8.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8666   -9.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2747  -10.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0741   -9.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6794  -10.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5074  -11.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1135  -11.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8918  -11.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0606  -10.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4532  -10.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9418  -10.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1290  -10.8549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4217  -11.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7961  -11.6012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9833  -11.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6504  -12.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5035  -11.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8372  -12.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043  -13.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9843  -13.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8010  -13.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1302  -13.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6524  -14.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6941  -13.3442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3620  -14.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2124  -12.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4994  -12.0419    0.0000 Cl  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:

   

   ALA3326184

   ---

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: 401.76

Molecular Weight (Monoisotopic): 401.0415

AlogP: 3.29

#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: 3.04

CX LogD: 1.22

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -1.26

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