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

ID: ALA3326185

PubChem CID: 11646890

Max Phase: Preclinical

Molecular Formula: C20H17N3O6

Molecular Weight: 395.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(-c2ccoc2C(=O)NNC(=O)c2ccc(O)c([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C20H17N3O6/c1-2-12-3-5-13(6-4-12)15-9-10-29-18(15)20(26)22-21-19(25)14-7-8-17(24)16(11-14)23(27)28/h3-11,24H,2H2,1H3,(H,21,25)(H,22,26)

Standard InChI Key:  SSZMEBZRSSEYHK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3869    0.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407    0.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -0.0707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014   -0.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3008   -0.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9061   -1.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -1.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402   -2.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185   -2.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2873   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6799   -0.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1685   -1.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3557   -1.6099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -2.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0228   -2.3562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2101   -2.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771   -3.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7302   -1.7796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0640   -3.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -4.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111   -4.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -5.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0835   -4.0992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -4.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5676   -3.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -2.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5567   -3.5963    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
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326185

   3-(4-ethylphenyl)-N'-(4-hydroxy-3-nitrobenzoyl)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: 395.37

Molecular Weight (Monoisotopic): 395.1117

AlogP: 3.20

#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: 3.39

CX LogD: 1.58

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -1.14

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