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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

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

HMDB0015258

Secondary Accession Numbers

HMDB15258

Metabolite Identification

Common Name

Dutasteride

Description

Dutasteride belongs to a class of drugs called 5-alpha-reductase inhibitors, which block the action of the 5-alpha-reductase enzymes that convert testosterone into dihydrotestosterone (DHT). Finasteride also belongs to this group, but while dutasteride inhibits both isoforms of 5-alpha reductase, finasteride inhibits only one. Even so, a clinical study done by GlaxoSmithKline, the EPICS trial, did not find dutasteride to be more effective than finasteride in treating BPH. [Wikipedia ]

Structure

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


  Mrv0541 04191212172D          

 42 46  0  0  1  0            999 V2000
    5.5645   -5.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5645   -6.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766   -6.8698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766   -5.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9851   -6.4614    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6938   -6.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4106   -6.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7008   -5.2247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.4312   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8507   -6.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6586   -4.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4062   -4.8198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  6  1  0  0  0  0
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  5  6  1  0  0  0  0
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 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
M  END

HMDB0015258
     RDKit          3D
Dutasteride
 67 71  0  0  0  0  0  0  0  0999 V2000
    0.5594    1.0835    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1220    0.2154   -3.0674 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    2.0585   -1.8074 F   0  0  0  0  0  0  0  0  0  0  0  0
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 32 67  1  0
M  END


  Mrv0541 04191212172D          

 42 46  0  0  1  0            999 V2000
    5.5645   -5.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5645   -6.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766   -6.8698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766   -5.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9886   -5.6364    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    7.6938   -6.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4312   -3.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0755   -5.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 17  1  0  0  0  0
  5  6  1  0  0  0  0
 17 22  1  1  0  0  0
  9 15  1  0  0  0  0
  5 23  1  1  0  0  0
 10 18  1  0  0  0  0
 21 24  1  0  0  0  0
 17 11  1  0  0  0  0
 24 25  2  0  0  0  0
 11 15  1  0  0  0  0
 24 26  1  0  0  0  0
  1  2  1  0  0  0  0
 26 27  1  0  0  0  0
  1  4  2  0  0  0  0
 27 28  2  0  0  0  0
  2  3  1  0  0  0  0
 28 29  1  0  0  0  0
  5  9  1  0  0  0  0
 29 30  2  0  0  0  0
  2 12  2  0  0  0  0
 30 31  1  0  0  0  0
  6 13  1  6  0  0  0
 31 32  2  0  0  0  0
 32 27  1  0  0  0  0
  6  7  1  0  0  0  0
 32 33  1  0  0  0  0
 18 14  1  6  0  0  0
  7  8  1  0  0  0  0
 10 16  1  1  0  0  0
 17 18  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
  9 34  1  6  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 33 37  1  0  0  0  0
 21 38  1  6  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 39 42  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015258

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1

> <INCHI_KEY>
JWJOTENAMICLJG-QWBYCMEYSA-N

> <FORMULA>
C27H30F6N2O2

> <MOLECULAR_WEIGHT>
528.5297

> <EXACT_MASS>
528.221147444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
50.12870007399721

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-14-carboxamide

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.792817784000001

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.400348116718117

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.561340514066647

> <JCHEM_PKA_STRONGEST_BASIC>
2.172701917237566

> <JCHEM_POLAR_SURFACE_AREA>
58.2

> <JCHEM_REFRACTIVITY>
127.89620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dutasteride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015258
     RDKit          3D
Dutasteride
 67 71  0  0  0  0  0  0  0  0999 V2000
    0.5594    1.0835    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -0.3398    0.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2683   -0.7464   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632   -0.6919   -1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.4768   -0.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2142    0.2927    0.9068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2784    0.4779    1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4872    1.1749    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0008    0.2568    0.2620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2775    0.6153   -0.2744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8600   -0.3484   -1.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0963   -0.4871   -1.2825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8823   -1.1275   -1.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895   -0.9480   -1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    0.0664   -0.8531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8380    1.3291   -1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0861   -0.5689    1.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5371   -0.2511    2.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060   -0.9842    2.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026   -1.2236    1.1999 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5054   -0.8469    1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.9329    2.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.4110   -0.1599 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935   -0.0756   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4832   -0.5060    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8271   -0.2091    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8715   -0.6693    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1268   -0.1898    0.8729 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6278   -0.2177    2.5380 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9353   -2.0644    1.3303 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498    0.5109   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    0.9385   -1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8472    0.6553   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    1.1738   -2.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5343    1.8715   -3.4625 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    0.2154   -3.0674 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    2.0585   -1.8074 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390    1.7268    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385    1.0969    0.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    1.5388   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125   -0.0711   -1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -1.7565   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039   -1.6379   -1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361    0.1091   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -1.4975    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    1.2791    0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646    1.0957    2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6407   -0.5128    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2420    1.2215    2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2353    2.1443    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -0.7580    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999    1.4978   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -1.8844   -2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383   -1.5826   -2.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6935    2.0287   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9217    1.8799   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    1.1343   -2.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -1.6519    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750   -0.7784    3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4213    0.8059    2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899   -1.9731    3.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051   -0.3864    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -2.3153    0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313   -0.3064   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471   -1.0955    1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2188    0.7344   -0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844    1.5105   -2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 26 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
 17  2  1  0
 33 24  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  1
  6 46  1  6
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  1
 10 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  6
 23 64  1  0
 25 65  1  0
 31 66  1  0
 32 67  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      10.387 -10.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.387 -12.061   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      11.716 -12.824   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      11.716  -9.744   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.045 -10.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.039 -12.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.362 -12.833   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.700 -12.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.375  -9.753   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.707 -10.542   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.738  -7.452   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.055 -12.833   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      13.024 -13.594   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0      17.029 -11.330   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      14.296  -8.359   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      15.692  -8.997   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      17.076  -8.239   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.045  -9.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.510 -10.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.448  -9.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.562  -7.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.068  -6.788   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.032  -8.974   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.569  -6.248   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.240  -5.471   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      19.907  -5.486   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      21.237  -6.263   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.223  -7.801   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.550  -8.578   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.890  -7.816   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.894  -6.268   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.565  -5.498   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.567  -3.958   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      14.362 -11.291   0.000  0.00  0.00           H+0
HETATM   35  F   UNK     0      23.902  -3.189   0.000  0.00  0.00           F+0
HETATM   36  F   UNK     0      21.235  -3.186   0.000  0.00  0.00           F+0
HETATM   37  F   UNK     0      22.562  -2.412   0.000  0.00  0.00           F+0
HETATM   38  H   UNK     0      20.038  -8.201   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0      22.541 -10.118   0.000  0.00  0.00           C+0
HETATM   40  F   UNK     0      21.203 -10.880   0.000  0.00  0.00           F+0
HETATM   41  F   UNK     0      23.870 -10.897   0.000  0.00  0.00           F+0
HETATM   42  F   UNK     0      22.543 -11.652   0.000  0.00  0.00           F+0
CONECT    1    2    4                                                       
CONECT    2    1    3   12                                                  
CONECT    3    6    2                                                       
CONECT    4    5    1                                                       
CONECT    5    4    6   23    9                                             
CONECT    6    3    5   13    7                                             
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9   15    5   10   34                                             
CONECT   10   18   16    8    9                                             
CONECT   11   17   15                                                       
CONECT   12    2                                                            
CONECT   13    6                                                            
CONECT   14   18                                                            
CONECT   15    9   11                                                       
CONECT   16   10                                                            
CONECT   17   21   22   11   18                                             
CONECT   18   19   10   14   17                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   24   38                                             
CONECT   22   17                                                            
CONECT   23    5                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27   33                                                  
CONECT   33   32   35   36   37                                             
CONECT   34    9                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   33                                                            
CONECT   38   21                                                            
CONECT   39   29   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

COMPND    HMDB0015258
HETATM    1  C1  UNL     1       0.559   1.084   0.505  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.096  -0.340   0.514  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.268  -0.746  -0.861  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.663  -0.692  -1.305  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.733  -0.477  -0.271  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.214   0.293   0.907  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.278   0.478   1.945  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.487   1.175   1.332  1.00  0.00           C  
HETATM    9  C9  UNL     1      -5.001   0.257   0.262  1.00  0.00           C  
HETATM   10  N1  UNL     1      -6.277   0.615  -0.274  1.00  0.00           N  
HETATM   11  C10 UNL     1      -6.860  -0.348  -1.175  1.00  0.00           C  
HETATM   12  O1  UNL     1      -8.096  -0.487  -1.282  1.00  0.00           O  
HETATM   13  C11 UNL     1      -5.882  -1.127  -1.932  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.590  -0.948  -1.793  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.983   0.066  -0.853  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.838   1.329  -1.663  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.086  -0.569   1.427  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.537  -0.251   2.747  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.806  -0.984   2.707  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.103  -1.224   1.200  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.505  -0.847   1.025  1.00  0.00           C  
HETATM   22  O2  UNL     1       3.256  -0.933   2.076  1.00  0.00           O  
HETATM   23  N2  UNL     1       3.122  -0.411  -0.160  1.00  0.00           N  
HETATM   24  C20 UNL     1       4.493  -0.076  -0.350  1.00  0.00           C  
HETATM   25  C21 UNL     1       5.483  -0.506   0.537  1.00  0.00           C  
HETATM   26  C22 UNL     1       6.827  -0.209   0.316  1.00  0.00           C  
HETATM   27  C23 UNL     1       7.872  -0.669   1.262  1.00  0.00           C  
HETATM   28  F1  UNL     1       9.127  -0.190   0.873  1.00  0.00           F  
HETATM   29  F2  UNL     1       7.628  -0.218   2.538  1.00  0.00           F  
HETATM   30  F3  UNL     1       7.935  -2.064   1.330  1.00  0.00           F  
HETATM   31  C24 UNL     1       7.150   0.511  -0.790  1.00  0.00           C  
HETATM   32  C25 UNL     1       6.188   0.938  -1.669  1.00  0.00           C  
HETATM   33  C26 UNL     1       4.847   0.655  -1.468  1.00  0.00           C  
HETATM   34  C27 UNL     1       3.868   1.174  -2.441  1.00  0.00           C  
HETATM   35  F4  UNL     1       4.534   1.872  -3.463  1.00  0.00           F  
HETATM   36  F5  UNL     1       3.122   0.215  -3.067  1.00  0.00           F  
HETATM   37  F6  UNL     1       3.013   2.059  -1.807  1.00  0.00           F  
HETATM   38  H1  UNL     1       0.039   1.727   1.261  1.00  0.00           H  
HETATM   39  H2  UNL     1       1.638   1.097   0.755  1.00  0.00           H  
HETATM   40  H3  UNL     1       0.497   1.539  -0.523  1.00  0.00           H  
HETATM   41  H4  UNL     1       0.313  -0.071  -1.567  1.00  0.00           H  
HETATM   42  H5  UNL     1       0.206  -1.757  -1.058  1.00  0.00           H  
HETATM   43  H6  UNL     1      -1.904  -1.638  -1.841  1.00  0.00           H  
HETATM   44  H7  UNL     1      -1.836   0.109  -2.082  1.00  0.00           H  
HETATM   45  H8  UNL     1      -2.991  -1.498   0.147  1.00  0.00           H  
HETATM   46  H9  UNL     1      -1.807   1.279   0.667  1.00  0.00           H  
HETATM   47  H10 UNL     1      -2.865   1.096   2.780  1.00  0.00           H  
HETATM   48  H11 UNL     1      -3.641  -0.513   2.300  1.00  0.00           H  
HETATM   49  H12 UNL     1      -5.242   1.221   2.137  1.00  0.00           H  
HETATM   50  H13 UNL     1      -4.235   2.144   0.877  1.00  0.00           H  
HETATM   51  H14 UNL     1      -5.093  -0.758   0.751  1.00  0.00           H  
HETATM   52  H15 UNL     1      -6.800   1.498  -0.066  1.00  0.00           H  
HETATM   53  H16 UNL     1      -6.270  -1.884  -2.628  1.00  0.00           H  
HETATM   54  H17 UNL     1      -3.938  -1.583  -2.398  1.00  0.00           H  
HETATM   55  H18 UNL     1      -4.693   2.029  -1.424  1.00  0.00           H  
HETATM   56  H19 UNL     1      -2.922   1.880  -1.539  1.00  0.00           H  
HETATM   57  H20 UNL     1      -3.966   1.134  -2.771  1.00  0.00           H  
HETATM   58  H21 UNL     1      -1.330  -1.652   1.353  1.00  0.00           H  
HETATM   59  H22 UNL     1      -1.175  -0.778   3.518  1.00  0.00           H  
HETATM   60  H23 UNL     1      -0.421   0.806   2.988  1.00  0.00           H  
HETATM   61  H24 UNL     1       0.690  -1.973   3.184  1.00  0.00           H  
HETATM   62  H25 UNL     1       1.605  -0.386   3.177  1.00  0.00           H  
HETATM   63  H26 UNL     1       0.920  -2.315   0.964  1.00  0.00           H  
HETATM   64  H27 UNL     1       2.531  -0.306  -1.051  1.00  0.00           H  
HETATM   65  H28 UNL     1       5.247  -1.096   1.413  1.00  0.00           H  
HETATM   66  H29 UNL     1       8.219   0.734  -0.954  1.00  0.00           H  
HETATM   67  H30 UNL     1       6.484   1.511  -2.538  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3   17   20
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6   15   45
CONECT    6    7   17   46
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   10   15   51
CONECT   10   11   52
CONECT   11   12   12   13
CONECT   13   14   14   53
CONECT   14   15   54
CONECT   15   16
CONECT   16   55   56   57
CONECT   17   18   58
CONECT   18   19   59   60
CONECT   19   20   61   62
CONECT   20   21   63
CONECT   21   22   22   23
CONECT   23   24   64
CONECT   24   25   25   33
CONECT   25   26   65
CONECT   26   27   31   31
CONECT   27   28   29   30
CONECT   31   32   66
CONECT   32   33   33   67
CONECT   33   34
CONECT   34   35   36   37
END

HMDB0015258
     RDKit          3D
Dutasteride
 67 71  0  0  0  0  0  0  0  0999 V2000
    0.5594    1.0835    0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -0.3398    0.5144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2683   -0.7464   -0.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6632   -0.6919   -1.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.4768   -0.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2142    0.2927    0.9068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2784    0.4779    1.9447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4872    1.1749    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0008    0.2568    0.2620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2775    0.6153   -0.2744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8600   -0.3484   -1.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0963   -0.4871   -1.2825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8823   -1.1275   -1.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895   -0.9480   -1.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    0.0664   -0.8531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8380    1.3291   -1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0861   -0.5689    1.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5371   -0.2511    2.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060   -0.9842    2.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1026   -1.2236    1.1999 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5054   -0.8469    1.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562   -0.9329    2.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.4110   -0.1599 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935   -0.0756   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4832   -0.5060    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8271   -0.2091    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8715   -0.6693    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1268   -0.1898    0.8729 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6278   -0.2177    2.5380 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9353   -2.0644    1.3303 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1498    0.5109   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    0.9385   -1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8472    0.6553   -1.4679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    1.1738   -2.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5343    1.8715   -3.4625 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    0.2154   -3.0674 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0134    2.0585   -1.8074 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0390    1.7268    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6385    1.0969    0.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966    1.5388   -0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125   -0.0711   -1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -1.7565   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9039   -1.6379   -1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361    0.1091   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9911   -1.4975    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8074    1.2791    0.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8646    1.0957    2.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6407   -0.5128    2.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2420    1.2215    2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2353    2.1443    0.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0928   -0.7580    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7999    1.4978   -0.0658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2701   -1.8844   -2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9383   -1.5826   -2.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6935    2.0287   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9217    1.8799   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    1.1343   -2.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -1.6519    1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1750   -0.7784    3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4213    0.8059    2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899   -1.9731    3.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051   -0.3864    3.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205   -2.3153    0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5313   -0.3064   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471   -1.0955    1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2188    0.7344   -0.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844    1.5105   -2.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 26 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
 17  2  1  0
 33 24  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  1
  6 46  1  6
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  1
 10 52  1  0
 13 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  6
 23 64  1  0
 25 65  1  0
 31 66  1  0
 32 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	ChEBI
alpha,alpha,alpha,Alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide	ChEBI
Avodart	Kegg
(5a,17b)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	Generator
(5Α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide	Generator
a,a,a,Alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5a-androst-1-ene-17b-carboxy-2',5'-xylidide	Generator
Α,α,α,alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5α-androst-1-ene-17β-carboxy-2',5'-xylidide	Generator
17beta-N-(2,5-Bis(trifluoromethyl))phenyl-carbamoyl-4-aza-5alpha-androst-1-en-3-one	HMDB
745, GG	HMDB

Chemical Formula

C₂₇H₃₀F₆N₂O₂

Average Molecular Weight

528.5297

Monoisotopic Molecular Weight

528.221147444

IUPAC Name

(1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-14-carboxamide

Traditional Name

dutasteride

CAS Registry Number

164656-23-9

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F

InChI Identifier

InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1

InChI Key

JWJOTENAMICLJG-QWBYCMEYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxosteroid
3-oxo-4-azasteroid
3-oxo-5-alpha-steroid
Oxosteroid
4-azasteroid
Azasteroid
Trifluoromethylbenzene
Anilide
N-arylamide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

delta-lactam (CHEBI:521033 )
aza-steroid (CHEBI:521033 )
(trifluoromethyl)benzenes (CHEBI:521033 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015258)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00091 g/L	Not Available
LogP	6.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00091 g/L	ALOGPS
logP	5.45	ALOGPS
logP	5.79	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	12.56	ChemAxon
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.9 m³·mol⁻¹	ChemAxon
Polarizability	50.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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-2H]-	249.166	30932474
DeepCCS	[M+Na]+	223.183	30932474
AllCCS	[M+H]+	219.2	32859911
AllCCS	[M+H-H2O]+	217.7	32859911
AllCCS	[M+NH4]+	220.6	32859911
AllCCS	[M+Na]+	221.0	32859911
AllCCS	[M-H]-	215.0	32859911
AllCCS	[M+Na-2H]-	216.0	32859911
AllCCS	[M+HCOO]-	217.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.07 minutes	32390414
Predicted by Siyang on May 30, 2022	21.9426 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3743.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	519.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	262.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	670.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1030.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1072.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1862.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	721.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2001.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	584.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	589.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	191.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	203.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dutasteride	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F	3280.0	Standard polar	33892256
Dutasteride	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F	3433.1	Standard non polar	33892256
Dutasteride	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC1=CC(=CC=C1C(F)(F)F)C(F)(F)F	3508.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dutasteride,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3284.2	Semi standard non polar	33892256
Dutasteride,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3296.4	Standard non polar	33892256
Dutasteride,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3763.8	Standard polar	33892256
Dutasteride,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3261.8	Semi standard non polar	33892256
Dutasteride,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3291.2	Standard non polar	33892256
Dutasteride,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3820.7	Standard polar	33892256
Dutasteride,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3188.4	Semi standard non polar	33892256
Dutasteride,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3383.5	Standard non polar	33892256
Dutasteride,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@H]4N([Si](C)(C)C)C(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)N(C1=CC(C(F)(F)F)=CC=C1C(F)(F)F)[Si](C)(C)C	3553.0	Standard polar	33892256
Dutasteride,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C=C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](C(=O)NC5=CC(C(F)(F)F)=CC=C5C(F)(F)F)CC[C@H]4[C@@H]3CC[C@@H]12	3490.9	Semi standard non polar	33892256
Dutasteride,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C=C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](C(=O)NC5=CC(C(F)(F)F)=CC=C5C(F)(F)F)CC[C@H]4[C@@H]3CC[C@@H]12	3483.3	Standard non polar	33892256
Dutasteride,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C=C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](C(=O)NC5=CC(C(F)(F)F)=CC=C5C(F)(F)F)CC[C@H]4[C@@H]3CC[C@@H]12	3841.1	Standard polar	33892256
Dutasteride,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4NC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3463.5	Semi standard non polar	33892256
Dutasteride,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4NC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3483.4	Standard non polar	33892256
Dutasteride,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4NC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3881.9	Standard polar	33892256
Dutasteride,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4N([Si](C)(C)C(C)(C)C)C(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3548.1	Semi standard non polar	33892256
Dutasteride,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4N([Si](C)(C)C(C)(C)C)C(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3747.9	Standard non polar	33892256
Dutasteride,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4N([Si](C)(C)C(C)(C)C)C(=O)C=C[C@]4(C)[C@H]3CC[C@]12C)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F	3673.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dutasteride GC-MS (Non-derivatized) - 70eV, Positive	splash10-0r00-0695380000-37d765dda5ec5e49b0fd	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 10V, Positive-QTOF	splash10-004i-0010190000-3420a2295d7f96d1d3c8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 20V, Positive-QTOF	splash10-0w4i-0566290000-0b4c4c43a1363f4cde3c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 40V, Positive-QTOF	splash10-0fka-2490010000-583fa26158a6ee3f69db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 10V, Negative-QTOF	splash10-004i-0000090000-6590720379fb16a92f43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 20V, Negative-QTOF	splash10-004i-1050090000-ceadcb8345b10a444f0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 40V, Negative-QTOF	splash10-0kbf-2190000000-a71ffb6ab0e5ccfce59b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 10V, Positive-QTOF	splash10-004i-0001090000-69b701f7be2c2462c87c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 20V, Positive-QTOF	splash10-00b9-0594370000-8a9228b409aa1db36766	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 40V, Positive-QTOF	splash10-00xr-0590000000-e41abf0c7f5b9d8fd56d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 10V, Negative-QTOF	splash10-004i-0000090000-754362aa78fcb9885806	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 20V, Negative-QTOF	splash10-004i-1020090000-9af76f2aa77fb2cdadf5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dutasteride 40V, Negative-QTOF	splash10-004i-0040090000-5354ee6cb84f313f4a81	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB01126	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01126	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01126

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5293502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dutasteride

METLIN ID

Not Available

PubChem Compound

6918296

PDB ID

Not Available

ChEBI ID

521033

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

Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. [PubMed:18318566 ]
Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. doi: 10.1016/j.juro.2008.10.014. Epub 2008 Dec 16. [PubMed:19091347 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. 3-oxo-5-alpha-steroid 4-dehydrogenase 2

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A2
Uniprot ID:: P31213
Molecular weight:: 28407.035

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Rathnayake D, Sinclair R: Male androgenetic alopecia. Expert Opin Pharmacother. 2010 Jun;11(8):1295-304. doi: 10.1517/14656561003752730. [PubMed:20426708 ]
Aggarwal S, Thareja S, Verma A, Bhardwaj TR, Kumar M: An overview on 5alpha-reductase inhibitors. Steroids. 2010 Feb;75(2):109-53. doi: 10.1016/j.steroids.2009.10.005. Epub 2009 Oct 30. [PubMed:19879888 ]
Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. [PubMed:19707263 ]
Goldenberg L, So A, Fleshner N, Rendon R, Drachenberg D, Elhilali M: The role of 5-alpha reductase inhibitors in prostate pathophysiology: Is there an additional advantage to inhibition of type 1 isoenzyme? Can Urol Assoc J. 2009 Jun;3(3 Suppl 2):S109-14. [PubMed:19543428 ]
Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. [PubMed:18318566 ]
Xu Y, Dalrymple SL, Becker RE, Denmeade SR, Isaacs JT: Pharmacologic basis for the enhanced efficacy of dutasteride against prostatic cancers. Clin Cancer Res. 2006 Jul 1;12(13):4072-9. [PubMed:16818707 ]
Rittmaster RS, Fleshner NE, Thompson IM: Pharmacological approaches to reducing the risk of prostate cancer. Eur Urol. 2009 May;55(5):1064-73. doi: 10.1016/j.eururo.2009.01.037. Epub 2009 Feb 5. [PubMed:19200641 ]
Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. doi: 10.1016/j.juro.2008.10.014. Epub 2008 Dec 16. [PubMed:19091347 ]

Enzyme Details

2. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A1
Uniprot ID:: P18405
Molecular weight:: 29458.18

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Xu Y, Dalrymple SL, Becker RE, Denmeade SR, Isaacs JT: Pharmacologic basis for the enhanced efficacy of dutasteride against prostatic cancers. Clin Cancer Res. 2006 Jul 1;12(13):4072-9. [PubMed:16818707 ]
Rathnayake D, Sinclair R: Male androgenetic alopecia. Expert Opin Pharmacother. 2010 Jun;11(8):1295-304. doi: 10.1517/14656561003752730. [PubMed:20426708 ]
Aggarwal S, Thareja S, Verma A, Bhardwaj TR, Kumar M: An overview on 5alpha-reductase inhibitors. Steroids. 2010 Feb;75(2):109-53. doi: 10.1016/j.steroids.2009.10.005. Epub 2009 Oct 30. [PubMed:19879888 ]
Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. [PubMed:19707263 ]
Goldenberg L, So A, Fleshner N, Rendon R, Drachenberg D, Elhilali M: The role of 5-alpha reductase inhibitors in prostate pathophysiology: Is there an additional advantage to inhibition of type 1 isoenzyme? Can Urol Assoc J. 2009 Jun;3(3 Suppl 2):S109-14. [PubMed:19543428 ]
Keam SJ, Scott LJ: Dutasteride: a review of its use in the management of prostate disorders. Drugs. 2008;68(4):463-85. [PubMed:18318566 ]
Rittmaster RS, Fleshner NE, Thompson IM: Pharmacological approaches to reducing the risk of prostate cancer. Eur Urol. 2009 May;55(5):1064-73. doi: 10.1016/j.eururo.2009.01.037. Epub 2009 Feb 5. [PubMed:19200641 ]
Shah SK, Trump DL, Sartor O, Tan W, Wilding GE, Mohler JL: Phase II study of Dutasteride for recurrent prostate cancer during androgen deprivation therapy. J Urol. 2009 Feb;181(2):621-6. doi: 10.1016/j.juro.2008.10.014. Epub 2008 Dec 16. [PubMed:19091347 ]

Enzyme Details

3. 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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 3A5

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.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Dutasteride (HMDB0015258)

MOL for HMDB0015258 (Dutasteride)

3D MOL for HMDB0015258 (Dutasteride)

3D SDF for HMDB0015258 (Dutasteride)

3D-SDF for HMDB0015258 (Dutasteride)

PDB for HMDB0015258 (Dutasteride)

3D PDB for HMDB0015258 (Dutasteride)

SMILES for HMDB0015258 (Dutasteride)

INCHI for HMDB0015258 (Dutasteride)

Structure for HMDB0015258 (Dutasteride)

3D Structure for HMDB0015258 (Dutasteride)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References