N'-(4-hydroxy-3-nitrobenzoyl)-3-m-tolylfuran-2-carbohydrazide

ID: ALA3326180

PubChem CID: 11632336

Max Phase: Preclinical

Molecular Formula: C19H15N3O6

Molecular Weight: 381.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)c1

Standard InChI:  InChI=1S/C19H15N3O6/c1-11-3-2-4-12(9-11)14-7-8-28-17(14)19(25)21-20-18(24)13-5-6-16(23)15(10-13)22(26)27/h2-10,23H,1H3,(H,20,24)(H,21,25)

Standard InChI Key:  LNKZJKAEWJRGOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   13.8011   -1.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0549   -1.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5076   -1.6886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9156   -2.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7150   -2.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3203   -2.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1483   -3.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7544   -4.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5327   -3.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7015   -3.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0941   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5827   -3.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7700   -3.2278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0626   -3.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4370   -3.9741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6243   -4.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2914   -4.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1444   -3.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4782   -4.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1453   -5.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6253   -6.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4420   -6.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7712   -5.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2933   -7.0398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3350   -5.7170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0029   -6.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8534   -5.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4780   -2.8097    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
 10 28  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326180

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

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: 381.34

Molecular Weight (Monoisotopic): 381.0961

AlogP: 2.94

#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: 2.95

CX LogD: 1.13

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.29

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