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

ID: ALA3326186

PubChem CID: 11704225

Max Phase: Preclinical

Molecular Formula: C21H19N3O6

Molecular Weight: 409.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C21H19N3O6/c1-12(2)13-3-5-14(6-4-13)16-9-10-30-19(16)21(27)23-22-20(26)15-7-8-18(25)17(11-15)24(28)29/h3-12,25H,1-2H3,(H,22,26)(H,23,27)

Standard InChI Key:  LXZWYGKYMHGWRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5074   -5.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9601   -5.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3681   -6.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1676   -6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7728   -7.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6008   -7.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2069   -8.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9853   -8.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2225   -7.5160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151   -8.0926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895   -8.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768   -8.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0778  -10.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945  -10.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -9.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7459  -11.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2168  -10.0052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5450  -10.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -9.3485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5929   -8.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4234   -9.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3699   -8.4499    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
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  9 10  1  0
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  5  6  1  0
  4 12  1  0
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 12 14  2  0
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 15 16  1  0
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 16 18  2  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
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 21 24  1  0
 20 25  1  0
 25 26  2  0
 25 27  1  0
  9 28  1  0
 28 29  1  0
 28 30  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326186

   N'-(4-hydroxy-3-nitrobenzoyl)-3-(4-propan-2-ylphenyl)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: 409.40

Molecular Weight (Monoisotopic): 409.1274

AlogP: 3.76

#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: 5.75

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 1.86

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -1.05

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