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

ID: ALA3326181

PubChem CID: 11625113

Max Phase: Preclinical

Molecular Formula: C19H15N3O6

Molecular Weight: 381.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)cc1

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

Standard InChI Key:  SHPBKXRTJSRXOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.8120   -7.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -7.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -7.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9265   -8.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7259   -8.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3312   -9.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1592   -9.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7653  -10.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5436  -10.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124   -9.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1050   -8.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5936   -9.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -9.4558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735  -10.0324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479  -10.2021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352  -10.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3022  -11.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553   -9.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891  -11.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561  -11.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362  -12.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529  -12.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7821  -11.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3042  -13.2678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584  -11.9450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866  -12.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425  -11.2883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1513  -10.6427    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
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326181

   N'-(4-hydroxy-3-nitrobenzoyl)-3-(4-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: -1.16

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