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

ID: ALA3326187

PubChem CID: 11633206

Max Phase: Preclinical

Molecular Formula: C22H21N3O6

Molecular Weight: 423.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1ccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C22H21N3O6/c1-2-3-4-14-5-7-15(8-6-14)17-11-12-31-20(17)22(28)24-23-21(27)16-9-10-19(26)18(13-16)25(29)30/h5-13,26H,2-4H2,1H3,(H,23,27)(H,24,28)

Standard InChI Key:  FDQHGPBWDBHZML-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.0101   -3.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2639   -3.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166   -3.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246   -4.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9241   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -4.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3573   -5.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9634   -6.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7417   -5.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9105   -5.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3031   -4.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -5.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790   -5.2213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2716   -5.7979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6460   -5.9676    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8333   -6.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004   -6.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3534   -5.3910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6872   -6.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3543   -7.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8343   -8.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6510   -8.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802   -7.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5024   -9.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -7.7105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7885   -8.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9444   -7.0538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3494   -6.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1799   -7.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -7.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -8.5535    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
 29 30  1  0
 30 31  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326187

   3-(4-Butylphenyl)-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: 423.43

Molecular Weight (Monoisotopic): 423.1430

AlogP: 3.98

#Rotatable Bonds: 7

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: 4.28

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.39

Np Likeness Score: -0.93

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