acifluorfen

ID: ALA222440

Cas Number: 50594-66-6

PubChem CID: 44073

Product Number: A114785M, Order Now?

Max Phase: Preclinical

Molecular Formula: C14H7ClF3NO5

Molecular Weight: 361.66

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Acifluorfen | Acifluorfen|50594-66-6|Acifluorfene|Acifluorofen|Tackle|5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid|5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid|Blazer|C14H7ClF3NO5|Acifluorfen [BSI:ISO]|5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid|Carbofluorfen|2-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid|Benzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-|OI60IB203A|DTXSID0020022|CHEBI:73172|MFCD00143541|5-(2-Chloro-4-(trifluorShow More⌵

Canonical SMILES:  O=C(O)c1cc(Oc2ccc(C(F)(F)F)cc2Cl)ccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)

Standard InChI Key:  NUFNQYOELLVIPL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.5980   -1.2121    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8055    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -0.4910    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3145   -1.9332    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826   -2.8768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -0.4066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1652   -1.6494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4518   -1.2351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499   -1.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0172   -1.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038   -2.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -1.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307   -1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1711   -1.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3038   -1.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4499   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1711   -2.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0172   -2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7307   -2.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0172   -0.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0
  2 16  1  0
  3 16  1  0
  4 16  1  0
  5 12  1  0
  5 14  1  0
  6 24  1  0
  7 24  2  0
  8 10  1  0
  9 10  2  0
 10 17  1  0
 11 16  1  0
 11 18  1  0
 11 20  2  0
 12 15  1  0
 12 21  2  0
 13 17  2  0
 13 19  1  0
 13 24  1  0
 14 19  2  0
 14 22  1  0
 15 18  2  0
 17 23  1  0
 20 21  1  0
 22 23  2  0
M  CHG  2   8  -1  10   1
M  END

Alternative Forms

1. Parent:

   

   ALA222440

   ACIFLUORFEN

2. Alternative Forms:

   

   ALA222440

   ACIFLUORFEN-NA

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: 361.66

Molecular Weight (Monoisotopic): 360.9965

AlogP: 4.76

#Rotatable Bonds: 4

Polar Surface Area: 89.67

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.86

CX Basic pKa: ┄

CX LogP: 4.55

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -1.37

References

1. Ramya TN, Mishra S, Karmodiya K, Surolia N, Surolia A..  (2007)  Inhibitors of nonhousekeeping functions of the apicoplast defy delayed death in Plasmodium falciparum.,  51  (1): [PMID:17060533] [10.1128/aac.00808-06]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. Zuo Y, Yang SG, Jiang LL, Hao GF, Wang ZF, Wu QY, Xi Z, Yang GF..  (2012)  Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors.,  20  (1): [PMID:22130420] [10.1016/j.bmc.2011.10.079]

6. Yu H, Yang H, Cui D, Lv L, Li B..  (2011)  Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates.,  59  (21): [PMID:21958315] [10.1021/jf2039444]

7. Sun Y, Li Z, Yan X, Wang L, Meng F.  (2009)  Study on the quantitative structuretoxicity relationships of benzoic acid derivatives in rats via oral LD50,  18  (9): [10.1007/s00044-009-9162-3]

8. ISHIDA S, IIDA T, KOHNO H, SATO Y, KUBO H, BOGER P, WAKABAYASHI K.  (1999)  Comparison of Phytotoxicities between 4-Fluorinated and Non-fluorinated 2-Chloro-5-(3, 4, 5, 6-tetrahydrophthalimido)benzoates,  24  (1): [10.1584/jpestics.24.28]

9. MATSUNARI K, YOSHIDA F, NAKAMURA Y, FUJITA T.  (1999)  Quantitative Structure-Activity Relationships of Herbicidal N-Alkyl-N-(4-substituted benzyl)-4-chloro-2-pentenamides against Echinochloa oryzicola,  24  (1): [10.1584/jpestics.24.7]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

13. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• SARS-CoV-2 Screening Data 2020-21