4-(5-(2-fluoro-4-hydroxyphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-2-(trifluoromethyl)benzonitrile

ID: ALA1082406

PubChem CID: 15951528

Max Phase: Preclinical

Molecular Formula: C20H13F4N3O2S

Molecular Weight: 435.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(N2C(=O)C3(CCC3)N(c3ccc(O)cc3F)C2=S)cc1C(F)(F)F

Standard InChI:  InChI=1S/C20H13F4N3O2S/c21-15-9-13(28)4-5-16(15)27-18(30)26(17(29)19(27)6-1-7-19)12-3-2-11(10-25)14(8-12)20(22,23)24/h2-5,8-9,28H,1,6-7H2

Standard InChI Key:  STEOIDKTSDJLHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.5558  -24.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5546  -24.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691  -25.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6273  -24.6150    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6526  -25.4762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9252  -25.8773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4347  -25.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971  -26.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6825  -24.4281    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7488  -25.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1686  -26.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9933  -26.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3992  -25.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9744  -25.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1511  -25.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2238  -25.8423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633  -27.2985    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1082406

   4-[5-(2-Fluoro-4-hydroxyphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-7-yl]-2-trifluoromethylbenzonitrile

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: 435.40

Molecular Weight (Monoisotopic): 435.0665

AlogP: 4.48

#Rotatable Bonds: 2

Polar Surface Area: 67.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.60

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.89

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.56

Np Likeness Score: -1.07

References

1. Jung ME, Ouk S, Yoo D, Sawyers CL, Chen C, Tran C, Wongvipat J..  (2010)  Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC).,  53  (7): [PMID:20218717] [10.1021/jm901488g]

Source

Source(1):

• Scientific Literature