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4,5,6,7-Tetrafluoro-2-((R)-1-naphthalen-1-yl-ethyl)-isoindole-1,3-dione

ID: ALA37162

PubChem CID: 12043696

Max Phase: Preclinical

Molecular Formula: C20H11F4NO2

Molecular Weight: 373.31

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  C[C@H](c1cccc2ccccc12)N1C(=O)c2c(F)c(F)c(F)c(F)c2C1=O

Standard InChI:  InChI=1S/C20H11F4NO2/c1-9(11-8-4-6-10-5-2-3-7-12(10)11)25-19(26)13-14(20(25)27)16(22)18(24)17(23)15(13)21/h2-9H,1H3/t9-/m1/s1

Standard InChI Key:  IMUGXJFOMQCMRN-SECBINFHSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
   -1.2208   -1.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2125   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2125   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -3.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2125   -3.2000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    0.1083    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -0.7250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -2.3750    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -0.8292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  1  1  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8  7  2  0
  9  6  2  0
 10  1  1  1
 11 10  1  0
 12 11  1  0
 13  5  2  0
 14  4  2  0
 15  7  1  0
 16  6  1  0
 17  9  1  0
 18  8  1  0
 19 12  1  0
 20 10  1  0
 21 11  2  0
 22 12  2  0
 23 21  1  0
 24 23  2  0
 25 19  2  0
 26 22  1  0
 27 26  2  0
 10 28  1  6
  2  3  2  0
  8  9  1  0
 24 19  1  0
 27 25  1  0
M  END

Associated Targets(Human)

HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WI-38 (2654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AR Tclin Androgen Receptor (11781 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

SC-3 (21 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

Biocomponents

Calculated Properties

Molecular Weight: 373.31Molecular Weight (Monoisotopic): 373.0726AlogP: 4.75#Rotatable Bonds: 2
Polar Surface Area: 37.38Molecular Species: HBA: 2HBD:
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 4.62CX LogD: 4.62
Aromatic Rings: 3Heavy Atoms: 27QED Weighted: 0.28Np Likeness Score: -0.55

References

1. Miyachi H, Azuma A, Kitamoto T, Hayashi K, Kato S, Koga M, Sato B, Hashimoto Y.  (1997)  Potent novel nonsteroidal androgen antagonists with a phthalimide skeleton,  (11): [10.1016/S0960-894X(97)00249-7]
2. Miyachi H, Azuma A, Hioki E, Iwasaki S, Hashimoto Y.  (1996)  Enantio-dependence of inducer-specific bidirectional regulation of tumor necrosis factor (TNF)-alpha production: Potent TNF- production inhibitors,  (19): [10.1016/0960-894X(96)00409-X]
3. Miyachi H, Azuma A, Ogasawara A, Uchimura E, Watanabe N, Kobayashi Y, Kato F, Kato M, Hashimoto Y..  (1997)  Novel biological response modifiers: phthalimides with tumor necrosis factor-alpha production-regulating activity.,  40  (18): [PMID:9288167] [10.1021/jm970109q]

Source