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N-(4-(3-(3-nitrophenyl)acryloyl)phenyl)furan-2-carboxamide

ID: ALA3115912

PubChem CID: 5733793

Max Phase: Preclinical

Molecular Formula: C20H14N2O5

Molecular Weight: 362.34

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cccc([N+](=O)[O-])c1)c1ccc(NC(=O)c2ccco2)cc1

Standard InChI:  InChI=1S/C20H14N2O5/c23-18(11-6-14-3-1-4-17(13-14)22(25)26)15-7-9-16(10-8-15)21-20(24)19-5-2-12-27-19/h1-13H,(H,21,24)/b11-6+

Standard InChI Key:  AFQFTGMILSTZMM-IZZDOVSWSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   17.1562   -3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1551   -4.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8699   -5.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5863   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5834   -3.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8681   -3.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2963   -3.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0123   -3.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2932   -2.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7252   -3.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4412   -3.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4411   -4.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1563   -5.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8702   -4.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8645   -3.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1487   -3.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5789   -3.3716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5728   -2.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2963   -3.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4403   -5.0558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7262   -4.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0507   -5.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7269   -3.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2697   -4.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7736   -5.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2469   -6.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0358   -5.9408    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  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  2  0
 17 19  1  0
 15 17  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 26 27  1  0
 24 25  1  0
 22 24  2  0
 25 26  2  0
 27 22  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

  1. Parent:

Associated Targets(Human)

HSPD1 Tbio HSP60/HSP10 (366 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DLD-1 (17511 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FHC (113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSPA14 Tbio Heat shock 70 kDa protein 14 (1 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

groL GroEL/GroES (1042 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae subsp. pneumoniae (55 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter cloacae (7976 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
groEL 60 kDa chaperonin (64 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 362.34Molecular Weight (Monoisotopic): 362.0903AlogP: 4.34#Rotatable Bonds: 6
Polar Surface Area: 102.45Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 13.82CX Basic pKa: CX LogP: 3.98CX LogD: 3.98
Aromatic Rings: 3Heavy Atoms: 27QED Weighted: 0.30Np Likeness Score: -1.44

References

1. Johnson SM, Sharif O, Mak PA, Wang HT, Engels IH, Brinker A, Schultz PG, Horwich AL, Chapman E..  (2014)  A biochemical screen for GroEL/GroES inhibitors.,  24  (3): [PMID:24418775] [10.1016/j.bmcl.2013.12.100]
2. Abdeen S, Salim N, Mammadova N, Summers CM, Frankson R, Ambrose AJ, Anderson GG, Schultz PG, Horwich AL, Chapman E, Johnson SM..  (2016)  GroEL/ES inhibitors as potential antibiotics.,  26  (13): [PMID:27184767] [10.1016/j.bmcl.2016.04.089]
3. Chitre S, Ray AM, Stevens M, Doud EH, Liechty H, Washburn A, Tepper K, Sivinski J, O'Hagan HM, Georgiadis MM, Chapman E, Johnson SM..  (2022)  Bis-aryl-α,β-unsaturated ketone (ABK) chaperonin inhibitors exhibit selective cytotoxicity to colorectal cancer cells that correlates with levels of aberrant HSP60 in the cytosol.,  75  [PMID:36356534] [10.1016/j.bmc.2022.117072]

Source