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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015260

Secondary Accession Numbers

HMDB15260

Metabolite Identification

Common Name

Bicalutamide

Description

Bicalutamide, also known as casodex or cosudex, belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Bicalutamide is a drug which is used for treatment (together with surgery or lhrh analogue) of advanced prostatic cancer. Based on a literature review a significant number of articles have been published on Bicalutamide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

2375
  Mrv0541 02231215162D          

 29 30  0  0  1  0            999 V2000
    7.3659   -1.6900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239   -0.0400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8476    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.0225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    2.0225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245   -2.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -2.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534   -0.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1 13  1  0  0  0  0
  1 16  1  0  0  0  0
  2 25  1  0  0  0  0
  3 28  1  0  0  0  0
  4 28  1  0  0  0  0
  5 28  1  0  0  0  0
  6 12  1  0  0  0  0
  9 15  2  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  0  0  0  0
 11 29  3  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 17 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 27  2  0  0  0  0
 24 26  2  0  0  0  0
 24 28  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
M  END

HMDB0015260
     RDKit          3D
Bicalutamide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.9724   -2.4738   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -1.8377    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -2.6771    1.5920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.5383    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -0.8492    0.2196 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.4377   -1.6009   -1.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253   -1.7212    1.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.6503    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    1.1117    1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    2.2994    1.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908    2.9839    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2914    4.1522    0.1196 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    2.5102   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3051    1.3287   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.6204    0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319   -2.2060    1.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.8114   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.5234    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950   -1.0170    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.6711    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942    0.1617    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853    0.5242    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039    0.8154    0.0721 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557    0.6599   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2499    1.5623   -1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2360    0.8569   -2.5864 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081    2.6741   -1.3223 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2825    1.9029   -2.8370 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363    0.3273   -0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -3.0313   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.7132   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -3.2318   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -2.9881    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989    0.1121   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    0.0241    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6596    0.5511    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    2.6799    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1160    3.0670   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368    0.9153   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -0.3611   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2483   -1.6769    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -1.0663    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    0.7453   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  3  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 24 29  2  0
 14  8  1  0
 29 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 29 43  1  0
M  END

2375
  Mrv0541 02231215162D          

 29 30  0  0  1  0            999 V2000
    7.3659   -1.6900    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.2239   -0.0400    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8476    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    2.0225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    2.0225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245   -2.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -2.4045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534   -0.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495   -0.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094   -0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1 13  1  0  0  0  0
  1 16  1  0  0  0  0
  2 25  1  0  0  0  0
  3 28  1  0  0  0  0
  4 28  1  0  0  0  0
  5 28  1  0  0  0  0
  6 12  1  0  0  0  0
  9 15  2  0  0  0  0
 10 15  1  0  0  0  0
 10 17  1  0  0  0  0
 11 29  3  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 17 23  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 24  1  0  0  0  0
 21 25  2  0  0  0  0
 22 25  1  0  0  0  0
 23 27  2  0  0  0  0
 24 26  2  0  0  0  0
 24 28  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015260

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

> <INCHI_KEY>
LKJPYSCBVHEWIU-UHFFFAOYSA-N

> <FORMULA>
C18H14F4N2O4S

> <MOLECULAR_WEIGHT>
430.373

> <EXACT_MASS>
430.061040456

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.684939604390834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.70929555

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.849797583664763

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.947143367840106

> <JCHEM_PKA_STRONGEST_BASIC>
-4.044979783200156

> <JCHEM_POLAR_SURFACE_AREA>
107.25999999999999

> <JCHEM_REFRACTIVITY>
96.58950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bicalutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015260
     RDKit          3D
Bicalutamide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.9724   -2.4738   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -1.8377    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -2.6771    1.5920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.5383    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -0.8492    0.2196 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.4377   -1.6009   -1.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253   -1.7212    1.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.6503    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    1.1117    1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    2.2994    1.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908    2.9839    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2914    4.1522    0.1196 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    2.5102   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3051    1.3287   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.6204    0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319   -2.2060    1.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.8114   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.5234    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950   -1.0170    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.6711    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942    0.1617    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853    0.5242    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039    0.8154    0.0721 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557    0.6599   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2499    1.5623   -1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2360    0.8569   -2.5864 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081    2.6741   -1.3223 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2825    1.9029   -2.8370 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363    0.3273   -0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -3.0313   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.7132   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -3.2318   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -2.9881    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989    0.1121   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    0.0241    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6596    0.5511    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    2.6799    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1160    3.0670   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368    0.9153   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -0.3611   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2483   -1.6769    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -1.0663    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    0.7453   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  3  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 24 29  2  0
 14  8  1  0
 29 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 29 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2375                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.750  -3.155   0.000  0.00  0.00           S+0
HETATM    2  F   UNK     0      19.085  -0.075   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.081   5.316   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       8.621   3.775   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       5.541   3.775   0.000  0.00  0.00           F+0
HETATM    6  O   UNK     0      10.312  -4.488   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.520  -4.488   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.980  -1.821   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.415  -3.155   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       9.748  -0.845   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       3.080   3.005   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      11.082  -3.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416  -3.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.852  -1.821   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -2.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.083  -2.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -0.075   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.083  -0.845   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.417  -3.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   1.465   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.417  -0.075   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.751  -2.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -0.845   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.081   2.235   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.751  -0.845   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.747   1.465   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.747  -0.075   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.081   3.775   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414   2.235   0.000  0.00  0.00           C+0
CONECT    1    7    8   13   16                                             
CONECT    2   25                                                            
CONECT    3   28                                                            
CONECT    4   28                                                            
CONECT    5   28                                                            
CONECT    6   12                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   15                                                            
CONECT   10   15   17                                                       
CONECT   11   29                                                            
CONECT   12    6   13   14   15                                             
CONECT   13    1   12                                                       
CONECT   14   12                                                            
CONECT   15    9   10   12                                                  
CONECT   16    1   18   19                                                  
CONECT   17   10   20   23                                                  
CONECT   18   16   21                                                       
CONECT   19   16   22                                                       
CONECT   20   17   24                                                       
CONECT   21   18   25                                                       
CONECT   22   19   25                                                       
CONECT   23   17   27                                                       
CONECT   24   20   26   28                                                  
CONECT   25    2   21   22                                                  
CONECT   26   24   27   29                                                  
CONECT   27   23   26                                                       
CONECT   28    3    4    5   24                                             
CONECT   29   11   26                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0243673
HETATM    1  C1  UNL     1       0.852   2.794  -1.810  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.740   1.963  -0.529  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.595   2.841   0.515  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.995   1.145  -0.485  1.00  0.00           C  
HETATM    5  S1  UNL     1       2.133   0.081   0.901  1.00  0.00           S  
HETATM    6  O2  UNL     1       1.012  -0.882   1.041  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.184   0.888   2.188  1.00  0.00           O  
HETATM    8  C4  UNL     1       3.634  -0.770   0.772  1.00  0.00           C  
HETATM    9  C5  UNL     1       4.779  -0.248   1.328  1.00  0.00           C  
HETATM   10  C6  UNL     1       5.991  -0.900   1.243  1.00  0.00           C  
HETATM   11  C7  UNL     1       6.044  -2.100   0.585  1.00  0.00           C  
HETATM   12  F1  UNL     1       7.211  -2.790   0.468  1.00  0.00           F  
HETATM   13  C8  UNL     1       4.915  -2.667   0.007  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.703  -1.970   0.117  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.479   1.118  -0.703  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.538   0.261  -1.599  1.00  0.00           O  
HETATM   17  N1  UNL     1      -1.549   1.319   0.170  1.00  0.00           N  
HETATM   18  C11 UNL     1      -2.793   0.678   0.232  1.00  0.00           C  
HETATM   19  C12 UNL     1      -3.742   1.031   1.195  1.00  0.00           C  
HETATM   20  C13 UNL     1      -4.962   0.400   1.253  1.00  0.00           C  
HETATM   21  C14 UNL     1      -5.299  -0.594   0.378  1.00  0.00           C  
HETATM   22  C15 UNL     1      -6.594  -1.256   0.450  1.00  0.00           C  
HETATM   23  N2  UNL     1      -7.628  -1.774   0.492  1.00  0.00           N  
HETATM   24  C16 UNL     1      -4.380  -0.952  -0.572  1.00  0.00           C  
HETATM   25  C17 UNL     1      -4.725  -2.019  -1.522  1.00  0.00           C  
HETATM   26  F2  UNL     1      -5.854  -1.601  -2.217  1.00  0.00           F  
HETATM   27  F3  UNL     1      -5.001  -3.159  -0.788  1.00  0.00           F  
HETATM   28  F4  UNL     1      -3.659  -2.225  -2.361  1.00  0.00           F  
HETATM   29  C18 UNL     1      -3.149  -0.311  -0.626  1.00  0.00           C  
HETATM   30  H1  UNL     1       1.706   3.481  -1.728  1.00  0.00           H  
HETATM   31  H2  UNL     1      -0.092   3.268  -2.077  1.00  0.00           H  
HETATM   32  H3  UNL     1       1.116   2.054  -2.608  1.00  0.00           H  
HETATM   33  H4  UNL     1       0.640   2.460   1.407  1.00  0.00           H  
HETATM   34  H5  UNL     1       2.036   0.535  -1.407  1.00  0.00           H  
HETATM   35  H6  UNL     1       2.851   1.840  -0.476  1.00  0.00           H  
HETATM   36  H7  UNL     1       4.738   0.714   1.856  1.00  0.00           H  
HETATM   37  H8  UNL     1       6.878  -0.497   1.673  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.989  -3.615  -0.506  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.851  -2.448  -0.347  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.422   2.086   0.925  1.00  0.00           H  
HETATM   41  H12 UNL     1      -3.526   1.813   1.914  1.00  0.00           H  
HETATM   42  H13 UNL     1      -5.700   0.683   2.012  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.501  -0.675  -1.418  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   15
CONECT    3   33
CONECT    4    5   34   35
CONECT    5    6    6    7    7
CONECT    5    8
CONECT    8    9    9   14
CONECT    9   10   36
CONECT   10   11   11   37
CONECT   11   12   13
CONECT   13   14   14   38
CONECT   14   39
CONECT   15   16   16   17
CONECT   17   18   40
CONECT   18   19   19   29
CONECT   19   20   41
CONECT   20   21   21   42
CONECT   21   22   24
CONECT   22   23   23   23
CONECT   24   25   29   29
CONECT   25   26   27   28
CONECT   29   43
END

HMDB0015260
     RDKit          3D
Bicalutamide
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.9724   -2.4738   -0.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8299   -1.8377    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -2.6771    1.5920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -0.5383    0.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3017   -0.8492    0.2196 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.4377   -1.6009   -1.0833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9253   -1.7212    1.2854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.6503    0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7645    1.1117    1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4754    2.2994    1.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5908    2.9839    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2914    4.1522    0.1196 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0128    2.5102   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3051    1.3287   -1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.6204    0.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1319   -2.2060    1.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.8114   -0.0182 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533   -0.5234    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950   -1.0170    1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9533   -0.6711    1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4942    0.1617    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8853    0.5242    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039    0.8154    0.0721 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557    0.6599   -0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2499    1.5623   -1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2360    0.8569   -2.5864 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8081    2.6741   -1.3223 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2825    1.9029   -2.8370 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363    0.3273   -0.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -3.0313   -1.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.7132   -1.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -3.2318   -0.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -2.9881    2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1989    0.1121   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5425    0.0241    1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6596    0.5511    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9333    2.6799    2.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1160    3.0670   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8368    0.9153   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544   -0.3611   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2483   -1.6769    1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -1.0663    1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222    0.7453   -1.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  2  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  3  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 24 29  2  0
 14  8  1  0
 29 18  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  9 36  1  0
 10 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 29 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Casodex	Kegg
Zeneca brand OF bicalutamide	HMDB
4'-Cyano-3-(4-fluorophenylsulfonyl)-2-hydroxy-2-methyl-3'-(trifluoromethyl)propionanilide	HMDB
Astra brand OF bicalutamide	HMDB
Cosudex	HMDB
AstraZeneca brand OF bicalutamide	HMDB

Chemical Formula

C₁₈H₁₄F₄N₂O₄S

Average Molecular Weight

430.373

Monoisotopic Molecular Weight

430.061040456

IUPAC Name

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

Traditional Name

bicalutamide

CAS Registry Number

90357-06-5

SMILES

CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F

InChI Identifier

InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)

InChI Key

LKJPYSCBVHEWIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Benzenesulfonyl group
Anilide
Benzonitrile
N-arylamide
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Tertiary alcohol
Sulfonyl
Sulfone
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carbonitrile
Nitrile
Organohalogen compound
Alkyl halide
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Alkyl fluoride
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0243673)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 - 193 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0093 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0093 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.71	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	107.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	96.59 m³·mol⁻¹	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	189.277	30932474
DeepCCS	[M-H]-	186.882	30932474
DeepCCS	[M-2H]-	220.108	30932474
DeepCCS	[M+Na]+	195.227	30932474
AllCCS	[M+H]+	191.9	32859911
AllCCS	[M+H-H2O]+	189.5	32859911
AllCCS	[M+NH4]+	194.1	32859911
AllCCS	[M+Na]+	194.8	32859911
AllCCS	[M-H]-	186.4	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	186.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bicalutamide	CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F	4632.6	Standard polar	33892256
Bicalutamide	CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F	2616.5	Standard non polar	33892256
Bicalutamide	CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F	2899.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bicalutamide,1TMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1	2924.1	Semi standard non polar	33892256
Bicalutamide,1TMS,isomer #2	CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C	2701.6	Semi standard non polar	33892256
Bicalutamide,2TMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C	2751.4	Semi standard non polar	33892256
Bicalutamide,2TMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C	3025.5	Standard non polar	33892256
Bicalutamide,2TMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C	3195.1	Standard polar	33892256
Bicalutamide,1TBDMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1	3168.1	Semi standard non polar	33892256
Bicalutamide,1TBDMS,isomer #2	CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	2958.0	Semi standard non polar	33892256
Bicalutamide,2TBDMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	3226.6	Semi standard non polar	33892256
Bicalutamide,2TBDMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	3523.2	Standard non polar	33892256
Bicalutamide,2TBDMS,isomer #1	CC(CS(=O)(=O)C1=CC=C(F)C=C1)(O[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C(C#N)C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	3324.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-08g3-8980200000-64d743e9fc999bfbcba9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (1 TMS) - 70eV, Positive	splash10-01p9-7953200000-a9b28d0415e04d7763bb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bicalutamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide LC-ESI-qTof , Positive-QTOF	splash10-014r-2950100000-4088c17274bcf0f095d4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide LC-ESI-qTof , Positive-QTOF	splash10-014r-0980100000-89a3faa58e22068394b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide LC-ESI-QFT , negative-QTOF	splash10-0a4r-0890000000-f2bd2727ffd1da47c463	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide , positive-QTOF	splash10-014r-2950100000-4088c17274bcf0f095d4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide , positive-QTOF	splash10-014r-0980100000-89a3faa58e22068394b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 45V, Negative-QTOF	splash10-000i-0910000000-975ab1680640ca2a45c6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 30V, Negative-QTOF	splash10-0a4i-0490000000-00705a3a1e877739adf9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 75V, Negative-QTOF	splash10-000i-1900000000-60b4010d9b8ad8f0e26a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 90V, Negative-QTOF	splash10-000i-2900000000-7653549d4fe376f62086	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 10V, Positive-QTOF	splash10-004i-0090000000-3d84326cb0f72ab380c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 35V, Positive-QTOF	splash10-02wr-0955700000-11e04cf7044e0290a38f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 30V, Positive-QTOF	splash10-0a4i-0920000000-9f948999a5a5c5b2a75c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 60V, Negative-QTOF	splash10-000i-1900000000-f4bca804dd2ab10d7ef6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 15V, Negative-QTOF	splash10-0a4i-0090000000-a5ddb76f73f4e1b74477	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 35V, Negative-QTOF	splash10-0a4i-0490000000-7f317ef8f9b7c134dd09	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 40V, Negative-QTOF	splash10-000i-0910000000-669162759e37780fd0ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 30V, Negative-QTOF	splash10-0a4i-0590000000-e34e938c197e8ec6a6a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 10V, Negative-QTOF	splash10-0a6r-0090600000-c6eaa8e8c0b2a3b7c032	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bicalutamide 45V, Positive-QTOF	splash10-000i-0910000000-a2e77819318784e0c2a0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 10V, Positive-QTOF	splash10-001i-0010900000-bb82a6e39969d267c6a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 20V, Positive-QTOF	splash10-00lr-0271900000-7c988dbd6f49d03a1406	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 40V, Positive-QTOF	splash10-0002-2920000000-26680dccacad423296a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 10V, Negative-QTOF	splash10-056r-0060900000-6a1879b598e45a16fa3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 20V, Negative-QTOF	splash10-0a4i-0090300000-b3a4c9df0fffd868683d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bicalutamide 40V, Negative-QTOF	splash10-01ot-9270000000-2d4ba654071403ab6b99	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01128	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01128	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01128

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2284

KEGG Compound ID

C08160

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bicalutamide

METLIN ID

Not Available

PubChem Compound

2375

PDB ID

Not Available

ChEBI ID

144093

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Cockshott ID: Bicalutamide: clinical pharmacokinetics and metabolism. Clin Pharmacokinet. 2004;43(13):855-78. [PubMed:15509184 ]

Enzyme Details

5. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Wang LG, Liu XM, Kreis W, Budman DR: Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor. Biochem Pharmacol. 1998 May 1;55(9):1427-33. [PubMed:10076535 ]
Chang HC, Miyamoto H, Marwah P, Lardy H, Yeh S, Huang KE, Chang C: Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11173-7. [PubMed:10500149 ]
Laufer M, Sinibaldi VJ, Carducci MA, Eisenberger MA: Rapid disease progression after the administration of bicalutamide in patients with metastatic prostate cancer. Urology. 1999 Oct;54(4):745. [PubMed:10754148 ]
Bouchal J, Kolar Z, Mad'arova J, Hlobilkova A, von Angerer E: The effects of natural ligands of hormone receptors and their antagonists on telomerase activity in the androgen sensitive prostatic cancer cell line LNCaP. Biochem Pharmacol. 2002 Mar 15;63(6):1177-81. [PubMed:11931851 ]
Hara T, Miyazaki J, Araki H, Yamaoka M, Kanzaki N, Kusaka M, Miyamoto M: Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome. Cancer Res. 2003 Jan 1;63(1):149-53. [PubMed:12517791 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Bicalutamide (HMDB0015260)

MOL for HMDB0015260 (Bicalutamide)

3D MOL for HMDB0015260 (Bicalutamide)

3D SDF for HMDB0015260 (Bicalutamide)

3D-SDF for HMDB0015260 (Bicalutamide)

PDB for HMDB0015260 (Bicalutamide)

3D PDB for HMDB0015260 (Bicalutamide)

SMILES for HMDB0015260 (Bicalutamide)

INCHI for HMDB0015260 (Bicalutamide)

Structure for HMDB0015260 (Bicalutamide)

3D Structure for HMDB0015260 (Bicalutamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References