(E)-4-(5-((3-methyl-5-oxo-1-p-tolyl-1H-pyrazol-4(5H)-ylidene)methyl)furan-2-yl)benzoic acid

ID: ALA4447199

PubChem CID: 22306611

Max Phase: Preclinical

Molecular Formula: C23H18N2O4

Molecular Weight: 386.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=NN(c2ccc(C)cc2)C(=O)/C1=C/c1ccc(-c2ccc(C(=O)O)cc2)o1

Standard InChI:  InChI=1S/C23H18N2O4/c1-14-3-9-18(10-4-14)25-22(26)20(15(2)24-25)13-19-11-12-21(29-19)16-5-7-17(8-6-16)23(27)28/h3-13H,1-2H3,(H,27,28)/b20-13+

Standard InChI Key:  GAGRGCXCIHIAGE-DEDYPNTBSA-N

Molfile:  

 
     RDKit          2D

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   17.2270   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0442   -4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2986   -3.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6356   -2.8189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9769   -3.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2018   -3.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0326   -2.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2561   -1.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6481   -2.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8218   -3.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5981   -3.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8705   -2.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0761   -3.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7458   -4.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5238   -4.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3366   -4.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8818   -5.2628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6287   -4.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5443   -4.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7451   -3.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3322   -5.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3299   -6.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0363   -6.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7455   -6.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7438   -5.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0368   -4.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4552   -6.5700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4554   -7.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1629   -6.1613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
  9 12  1  0
  3 13  1  0
  1 14  2  0
  2 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 27 28  1  0
 27 29  2  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4447199

   4-[5-[(E)-[3-methyl-1-(4-methylphenyl)-5-oxopyrazol-4-ylidene]methyl]furan-2-yl]benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 386.41

Molecular Weight (Monoisotopic): 386.1267

AlogP: 4.76

#Rotatable Bonds: 4

Polar Surface Area: 83.11

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.90

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.19

References

1. Hayes KE, Batsomboon P, Chen WC, Johnson BD, Becker A, Eschrich S, Yang Y, Robart AR, Dudley GB, Geldenhuys WJ, Hazlehurst LA..  (2019)  Inhibition of the FAD containing ER oxidoreductin 1 (Ero1) protein by EN-460 as a strategy for treatment of multiple myeloma.,  27  (8): [PMID:30850265] [10.1016/j.bmc.2019.02.016]

Source

Source(1):

• Scientific Literature