N'-(4-hydroxy-3-nitrobenzoyl)-3-phenylfuran-2-carbohydrazide

ID: ALA3326178

PubChem CID: 11617576

Max Phase: Preclinical

Molecular Formula: C18H13N3O6

Molecular Weight: 367.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NNC(=O)c1occc1-c1ccccc1)c1ccc(O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C18H13N3O6/c22-15-7-6-12(10-14(15)21(25)26)17(23)19-20-18(24)16-13(8-9-27-16)11-4-2-1-3-5-11/h1-10,22H,(H,19,23)(H,20,24)

Standard InChI Key:  BUDXBKRZWUDJFO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.5348   -2.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7885   -2.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2412   -2.6213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6493   -3.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4487   -3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0540   -3.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8820   -4.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4881   -5.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2664   -4.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4352   -3.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8278   -3.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3164   -4.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5036   -4.1606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7962   -4.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707   -4.9069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579   -4.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -5.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781   -4.3303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2118   -5.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8789   -6.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -7.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -7.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5048   -6.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -7.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687   -6.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366   -7.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5870   -5.9931    0.0000 O   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
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3326178

   N'-(4-hydroxy-3-nitrobenzoyl)-3-phenylfuran-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: 367.32

Molecular Weight (Monoisotopic): 367.0804

AlogP: 2.64

#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: 2.43

CX LogD: 0.62

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -1.12

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