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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 02:51:54 UTC

HMDB ID

HMDB0015240

Secondary Accession Numbers

HMDB15240

Metabolite Identification

Common Name

Trilostane

Description

Trilostane is only found in individuals that have used or taken this drug. It is an inhibitor of 3 beta-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It was withdrawn from the United States market in April 1994. [Wikipedia ]Trilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.

Structure

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

1108
  Mrv0541 02231215152D          

 28 32  0  0  1  0            999 V2000
    5.1232   -1.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3475    3.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981   -3.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -2.8376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078   -0.8126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3977   -1.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3977    0.3825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4106    1.2122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6951    1.6327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4106   -2.0408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0878   -0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878   -0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    1.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0264    1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    2.4379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0178   -0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6962    2.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -2.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0082    2.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -2.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584   -0.3388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522    0.6969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.9470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356   -2.5890    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 11  1  0  0  0  0
 18  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 24  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 16  1  0  0  0  0
  5 19  1  1  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  7 25  1  6  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 26  1  1  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
  9 27  1  6  0  0  0
 10 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 22  1  1  0  0  0
 11 21  1  0  0  0  0
 11 28  1  1  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 23  1  0  0  0  0
 17 20  1  0  0  0  0
 18 20  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
M  END

HMDB0015240
     RDKit          3D
Trilostane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.2469   -0.0269   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1491    0.7562   -0.8321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1504    1.8439   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    1.2603   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339    0.2339   -0.1809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4977   -0.8643   -0.0602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1984   -1.9128    0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -2.2526    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1451   -1.0563    1.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6625   -0.1434    2.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -0.5425    1.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7400    0.7109    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4392    1.4225    2.3871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999    1.1958    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530    2.4282   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840    3.4163   -0.4450 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733    0.4613   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.4225   -0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7239   -1.4847   -1.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -0.1454    0.3568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9686   -1.0413    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451   -0.1813   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332    1.1722   -0.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2114    1.7518   -1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9351    0.5614   -2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -1.0107   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.1393   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816    2.3259    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    2.6527   -1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9675   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9196    2.1263   -1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409    0.7400    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7655   -1.2985   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -1.6550    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -2.8692    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -2.6153    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -3.1340    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -1.0725    2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0731    2.2688    2.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -0.1776   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647    1.1023   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967   -1.9570   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.9531   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -2.2664   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525    0.4748    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705   -1.2755    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819   -1.9730   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6305   -0.6007   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722    0.0008    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417    1.8042    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    1.3940   -1.5041 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  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  6
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  1
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  1
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  1
 24 51  1  0
M  END

1108
  Mrv0541 02231215152D          

 28 32  0  0  1  0            999 V2000
    5.1232   -1.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3475    3.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6981   -3.2579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -2.8376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078   -0.8126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3977   -1.2109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7078   -0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3977    0.3825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4106    1.2122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6951    1.6327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4106   -2.0408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0878   -0.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0878   -0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764    1.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828   -1.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0264    1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8750    2.4379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0178   -0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6962    2.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -2.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0082    2.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9764   -2.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -2.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584   -0.3388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9522    0.6969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    0.9470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7356   -2.5890    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  6  0  0  0
  1 11  1  0  0  0  0
 18  2  1  1  0  0  0
  3 21  1  0  0  0  0
  4 24  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 16  1  0  0  0  0
  5 19  1  1  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  7 25  1  6  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  8 26  1  1  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
  9 27  1  6  0  0  0
 10 15  1  0  0  0  0
 10 18  1  0  0  0  0
 10 22  1  1  0  0  0
 11 21  1  0  0  0  0
 11 28  1  1  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 23  1  0  0  0  0
 17 20  1  0  0  0  0
 18 20  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015240

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1

> <INCHI_KEY>
KVJXBPDAXMEYOA-CXANFOAXSA-N

> <FORMULA>
C20H27NO3

> <MOLECULAR_WEIGHT>
329.4333

> <EXACT_MASS>
329.199093735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.96495621972632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0²,⁸.0⁶,⁸.0¹²,¹⁶]octadec-4-ene-4-carbonitrile

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.300783866666666

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.3777053517066

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.231169873958983

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8838175250659647

> <JCHEM_POLAR_SURFACE_AREA>
76.78

> <JCHEM_REFRACTIVITY>
90.17459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trilostane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015240
     RDKit          3D
Trilostane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.2469   -0.0269   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1491    0.7562   -0.8321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1504    1.8439   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    1.2603   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339    0.2339   -0.1809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4977   -0.8643   -0.0602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1984   -1.9128    0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -2.2526    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1451   -1.0563    1.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6625   -0.1434    2.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -0.5425    1.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7400    0.7109    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4392    1.4225    2.3871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999    1.1958    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530    2.4282   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840    3.4163   -0.4450 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733    0.4613   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.4225   -0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7239   -1.4847   -1.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -0.1454    0.3568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9686   -1.0413    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451   -0.1813   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332    1.1722   -0.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2114    1.7518   -1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9351    0.5614   -2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -1.0107   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.1393   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816    2.3259    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    2.6527   -1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9675   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9196    2.1263   -1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409    0.7400    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7655   -1.2985   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -1.6550    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -2.8692    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -2.6153    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -3.1340    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -1.0725    2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0731    2.2688    2.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -0.1776   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647    1.1023   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967   -1.9570   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.9531   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -2.2664   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525    0.4748    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705   -1.2755    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819   -1.9730   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6305   -0.6007   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722    0.0008    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417    1.8042    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    1.3940   -1.5041 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  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  6
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  1
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  1
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  1
 24 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1108                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.563  -3.014   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.249   5.665   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.903  -6.081   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.974  -5.297   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.921  -1.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.209  -2.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.921  -0.030   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.209   0.714   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.233   2.263   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.898   3.048   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.233  -3.809   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.497  -1.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.497  -0.030   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.568   0.724   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.556   2.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.568  -2.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.383   3.287   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.233   4.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.633  -0.773   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.766   4.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.898  -4.594   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.615   3.801   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.556  -3.820   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.265  -4.558   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       5.896  -0.632   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       9.244   1.301   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       9.315   1.768   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.840  -4.833   0.000  0.00  0.00           H+0
CONECT    1    6   11                                                       
CONECT    2   18                                                            
CONECT    3   21                                                            
CONECT    4   24                                                            
CONECT    5    6    7   16   19                                             
CONECT    6    1    5   11   12                                             
CONECT    7    5    8   14   25                                             
CONECT    8    7    9   13   26                                             
CONECT    9    8   10   17   27                                             
CONECT   10    9   15   18   22                                             
CONECT   11    1    6   21   28                                             
CONECT   12    6   13                                                       
CONECT   13    8   12                                                       
CONECT   14    7   15                                                       
CONECT   15   10   14                                                       
CONECT   16    5   23                                                       
CONECT   17    9   20                                                       
CONECT   18    2   10   20                                                  
CONECT   19    5                                                            
CONECT   20   17   18                                                       
CONECT   21    3   11   23                                                  
CONECT   22   10                                                            
CONECT   23   16   21   24                                                  
CONECT   24    4   23                                                       
CONECT   25    7                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0015240
HETATM    1  C1  UNL     1      -2.247  -0.027  -2.111  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.149   0.756  -0.832  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.150   1.844  -0.886  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.209   1.260  -1.182  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.534   0.234  -0.181  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.498  -0.864  -0.060  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.198  -1.913   0.926  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.255  -2.253   1.136  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.145  -1.056   1.037  1.00  0.00           C  
HETATM   10  O1  UNL     1       1.663  -0.143   2.144  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.089  -0.542   1.862  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.740   0.711   1.436  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.439   1.422   2.387  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.700   1.196   0.216  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.353   2.428  -0.152  1.00  0.00           C  
HETATM   16  N1  UNL     1       4.884   3.416  -0.445  1.00  0.00           N  
HETATM   17  C14 UNL     1       2.973   0.461  -0.811  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.883  -0.422  -0.313  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.724  -1.485  -1.386  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.788  -0.145   0.357  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.969  -1.041   0.414  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.145  -0.181  -0.048  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.533   1.172  -0.432  1.00  0.00           C  
HETATM   24  O3  UNL     1      -4.211   1.752  -1.492  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.935   0.561  -2.786  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.701  -1.011  -1.949  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.313  -0.139  -2.655  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.082   2.326   0.111  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.411   2.653  -1.603  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.347   0.967  -2.232  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.920   2.126  -1.022  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.541   0.740   0.831  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.765  -1.299  -1.069  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.682  -1.655   1.891  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.694  -2.869   0.590  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.328  -2.615   2.209  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.601  -3.134   0.555  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.544  -1.072   2.702  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.073   2.269   2.842  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.740  -0.178  -1.349  1.00  0.00           H  
HETATM   41  H17 UNL     1       2.565   1.102  -1.616  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.697  -1.957  -1.641  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.396  -0.953  -2.307  1.00  0.00           H  
HETATM   44  H20 UNL     1       1.012  -2.266  -1.177  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.652   0.475   1.238  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.170  -1.276   1.490  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.882  -1.973  -0.160  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.631  -0.601  -0.940  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.872   0.001   0.742  1.00  0.00           H  
HETATM   50  H26 UNL     1      -3.542   1.804   0.484  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.131   1.394  -1.504  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   20   23
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   18   32
CONECT    6    7   20   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   11   18
CONECT   10   11
CONECT   11   12   38
CONECT   12   13   14   14
CONECT   13   39
CONECT   14   15   17
CONECT   15   16   16   16
CONECT   17   18   40   41
CONECT   18   19
CONECT   19   42   43   44
CONECT   20   21   45
CONECT   21   22   46   47
CONECT   22   23   48   49
CONECT   23   24   50
CONECT   24   51
END

HMDB0015240
     RDKit          3D
Trilostane
 51 55  0  0  0  0  0  0  0  0999 V2000
   -2.2469   -0.0269   -2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1491    0.7562   -0.8321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1504    1.8439   -0.8863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2089    1.2603   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339    0.2339   -0.1809 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4977   -0.8643   -0.0602 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1984   -1.9128    0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2550   -2.2526    1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1451   -1.0563    1.0366 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6625   -0.1434    2.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -0.5425    1.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7400    0.7109    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4392    1.4225    2.3871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999    1.1958    0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3530    2.4282   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840    3.4163   -0.4450 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733    0.4613   -0.8110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -0.4225   -0.3134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7239   -1.4847   -1.3856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7880   -0.1454    0.3568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9686   -1.0413    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451   -0.1813   -0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5332    1.1722   -0.4324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2114    1.7518   -1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9351    0.5614   -2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7015   -1.0107   -1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.1393   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816    2.3259    0.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111    2.6527   -1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3466    0.9675   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9196    2.1263   -1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409    0.7400    0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7655   -1.2985   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6818   -1.6550    1.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -2.8692    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3279   -2.6153    2.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -3.1340    0.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -1.0725    2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0731    2.2688    2.8419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396   -0.1776   -1.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647    1.1023   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967   -1.9570   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3961   -0.9531   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -2.2664   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525    0.4748    1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705   -1.2755    1.4903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819   -1.9730   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6305   -0.6007   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722    0.0008    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417    1.8042    0.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1310    1.3940   -1.5041 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  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  1  0
 18 19  1  6
  6 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20  2  1  0
 23  2  1  0
 18  5  1  0
 11  9  1  0
 18  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  6
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 11 38  1  1
 13 39  1  0
 17 40  1  0
 17 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  1
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  1
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Trilostano	ChEBI
Trilostanum	ChEBI
Desopan	Kegg
Modrenal	Kegg
4alpha,5-Epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile	HMDB

Chemical Formula

C₂₀H₂₇NO₃

Average Molecular Weight

329.4333

Monoisotopic Molecular Weight

329.199093735

IUPAC Name

(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0²,⁸.0⁶,⁸.0¹²,¹⁶]octadec-4-ene-4-carbonitrile

Traditional Name

trilostane

CAS Registry Number

13647-35-3

SMILES

[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O

InChI Identifier

InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1

InChI Key

KVJXBPDAXMEYOA-CXANFOAXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Cyclic alcohol
Secondary alcohol
Dialkyl ether
Enol
Oxirane
Ether
Carbonitrile
Nitrile
Organoheterocyclic compound
Oxacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

17beta-hydroxy steroid (CHEBI:32260 )
androstanoid (CHEBI:32260 )
3-hydroxy steroid (CHEBI:32260 )

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: HMDB0015240)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	264 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.059 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.3	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.23	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.17 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	5	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-2H]-	209.642	30932474
DeepCCS	[M+Na]+	184.076	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.2	32859911
AllCCS	[M+NH4]+	184.6	32859911
AllCCS	[M+Na]+	185.3	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	185.6	32859911
AllCCS	[M+HCOO]-	185.7	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.	5.18 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4845 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2540.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	774.0 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	617.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1034.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	422.6 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	1535.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	277.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.6 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	93.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trilostane	[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O	3483.5	Standard polar	33892256
Trilostane	[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O	2653.8	Standard non polar	33892256
Trilostane	[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O	3010.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trilostane,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2928.7	Semi standard non polar	33892256
Trilostane,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O[Si](C)(C)C)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O	2841.2	Semi standard non polar	33892256
Trilostane,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CC[C@@]45O[C@@H]4C(O[Si](C)(C)C)=C(C#N)C[C@]35C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2840.5	Semi standard non polar	33892256
Trilostane,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@@]45O[C@@H]4C(O)=C(C#N)C[C@]5(C)[C@H]3CC[C@]12C	3183.6	Semi standard non polar	33892256
Trilostane,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O)CC[C@H]4[C@@H]3CC[C@]23O[C@H]13	3101.2	Semi standard non polar	33892256
Trilostane,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]4[C@@H]3CC[C@]23O[C@H]13	3323.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trilostane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ik9-3697000000-af2f49f13d139eac8699	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trilostane GC-MS (2 TMS) - 70eV, Positive	splash10-0adi-4074900000-0871d982b0c9c78ee04b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trilostane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trilostane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 45V, Negative-QTOF	splash10-002f-9075000000-1da8d2bce11b199e6ae7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 60V, Negative-QTOF	splash10-000x-8490000000-5c94811dae50400973f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 30V, Negative-QTOF	splash10-004i-1009000000-3c90bf59829f923f3ecb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 15V, Negative-QTOF	splash10-004i-0009000000-06fd800fcd666ed6b409	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 75V, Positive-QTOF	splash10-014i-0930000000-724aa1c092e58c7c72c1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 90V, Positive-QTOF	splash10-0006-4950000000-252ada46341ba1485344	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 30V, Positive-QTOF	splash10-0udi-0092000000-03cdb20a05a4dd66ccd5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 15V, Positive-QTOF	splash10-001i-0009000000-5008f2d6d59863b60347	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 45V, Positive-QTOF	splash10-00r7-0191000000-66f49b3ef9aaa33ee43b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 60V, Positive-QTOF	splash10-014i-0590000000-4fa0eb545e6d0b7ed6d9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 45V, Positive-QTOF	splash10-00r7-0191000000-a97ac92908c84413eb43	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 90V, Negative-QTOF	splash10-01b9-4920000000-feacd7efa065a9b6bfcf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 75V, Negative-QTOF	splash10-01dl-5950000000-7b266af2b926fe90bbcd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Trilostane 75V, Positive-QTOF	splash10-014i-0930000000-0e6461981c695c95e322	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 10V, Positive-QTOF	splash10-03e9-0019000000-8b1592dcd1075be8e6c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 20V, Positive-QTOF	splash10-03ea-0289000000-5aba04fec65a6b4e7e80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 40V, Positive-QTOF	splash10-0006-9230000000-a7730c61179e8cf71251	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 10V, Negative-QTOF	splash10-004i-0009000000-2793c8c4f9445fececbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 20V, Negative-QTOF	splash10-01t9-0029000000-98f981d26f779dc0bd6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 40V, Negative-QTOF	splash10-0292-5193000000-a1e424641cac8997b54b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 10V, Positive-QTOF	splash10-001i-0009000000-ae1c08c80815d3354b58	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 20V, Positive-QTOF	splash10-0a59-3986000000-143177beea0b413dd522	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 40V, Positive-QTOF	splash10-0bt9-5955000000-c4f6dc5057a30e34a5de	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 10V, Negative-QTOF	splash10-004i-0009000000-93fb7ff56b0b7a4bf0f2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trilostane 20V, Negative-QTOF	splash10-004i-0009000000-2b46248186d5598f4196	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 DB01108	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01108	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01108

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

570949

KEGG Compound ID

C12580

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trilostane

METLIN ID

Not Available

PubChem Compound

656583

PDB ID

Not Available

ChEBI ID

32260

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

Komanicky P, Spark RF, Melby JC: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. J Clin Endocrinol Metab. 1978 Nov;47(5):1042-51. [PubMed:233687 ]
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. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Puddefoot JR, Barker S, Vinson GP: Trilostane in advanced breast cancer. Expert Opin Pharmacother. 2006 Dec;7(17):2413-9. [PubMed:17109615 ]
Puddefoot JR, Barker S, Glover HR, Malouitre SD, Vinson GP: Non-competitive steroid inhibition of oestrogen receptor functions. Int J Cancer. 2002 Sep 1;101(1):17-22. [PubMed:12209583 ]
Barker S, Malouitre SD, Glover HR, Puddefoot JR, Vinson GP: Comparison of effects of 4-hydroxy tamoxifen and trilostane on oestrogen-regulated gene expression in MCF-7 cells: up-regulation of oestrogen receptor beta. J Steroid Biochem Mol Biol. 2006 Aug;100(4-5):141-51. Epub 2006 Jun 27. [PubMed:16806905 ]

Enzyme Details

2. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Puddefoot JR, Barker S, Vinson GP: Trilostane in advanced breast cancer. Expert Opin Pharmacother. 2006 Dec;7(17):2413-9. [PubMed:17109615 ]
Puddefoot JR, Barker S, Glover HR, Malouitre SD, Vinson GP: Non-competitive steroid inhibition of oestrogen receptor functions. Int J Cancer. 2002 Sep 1;101(1):17-22. [PubMed:12209583 ]
Barker S, Malouitre SD, Glover HR, Puddefoot JR, Vinson GP: Comparison of effects of 4-hydroxy tamoxifen and trilostane on oestrogen-regulated gene expression in MCF-7 cells: up-regulation of oestrogen receptor beta. J Steroid Biochem Mol Biol. 2006 Aug;100(4-5):141-51. Epub 2006 Jun 27. [PubMed:16806905 ]

Enzyme Details

3. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

References

Naville D, Keeney DS, Jenkin G, Murry BA, Head JR, Mason JI: Regulation of expression of male-specific rat liver microsomal 3 beta-hydroxysteroid dehydrogenase. Mol Endocrinol. 1991 Aug;5(8):1090-100. [PubMed:1944305 ]
Takahashi M, Luu-The V, Labrie F: Inhibitory effect of synthetic progestins, 4-MA and cyanoketone on human placental 3 beta-hydroxysteroid dehydrogenase/5----4-ene-isomerase activity. J Steroid Biochem Mol Biol. 1990 Oct;37(2):231-6. [PubMed:2268554 ]
Suzuki S, Endo Y, Tanaka S, Iizuka R: Indirect immunofluorescence studies on the steroid-producing activity of hamster ova. Am J Obstet Gynecol. 1984 Jan 1;148(1):76-85. [PubMed:6362415 ]
Duffy DM, Hess DL, Stouffer RL: Acute administration of a 3 beta-hydroxysteroid dehydrogenase inhibitor to rhesus monkeys at the midluteal phase of the menstrual cycle: evidence for possible autocrine regulation of the primate corpus luteum by progesterone. J Clin Endocrinol Metab. 1994 Dec;79(6):1587-94. [PubMed:7989460 ]
Mensah-Nyagan AG, Feuilloley M, Dupont E, Do-Rego JL, Leboulenger F, Pelletier G, Vaudry H: Immunocytochemical localization and biological activity of 3 beta-hydroxysteroid dehydrogenase in the central nervous system of the frog. J Neurosci. 1994 Dec;14(12):7306-18. [PubMed:7996177 ]
Cooke GM: Differential effects of trilostane and cyanoketone on the 3 beta-hydroxysteroid dehydrogenase-isomerase reactions in androgen and 16-androstene biosynthetic pathways in the pig testis. J Steroid Biochem Mol Biol. 1996 Apr;58(1):95-101. [PubMed:8809191 ]
Igaz P, Tombol Z, Szabo PM, Liko I, Racz K: Steroid biosynthesis inhibitors in the therapy of hypercortisolism: theory and practice. Curr Med Chem. 2008;15(26):2734-47. [PubMed:18991633 ]

Enzyme Details

4. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

References

Naville D, Keeney DS, Jenkin G, Murry BA, Head JR, Mason JI: Regulation of expression of male-specific rat liver microsomal 3 beta-hydroxysteroid dehydrogenase. Mol Endocrinol. 1991 Aug;5(8):1090-100. [PubMed:1944305 ]
Cooke GM: Differential effects of trilostane and cyanoketone on the 3 beta-hydroxysteroid dehydrogenase-isomerase reactions in androgen and 16-androstene biosynthetic pathways in the pig testis. J Steroid Biochem Mol Biol. 1996 Apr;58(1):95-101. [PubMed:8809191 ]
Takahashi M, Luu-The V, Labrie F: Inhibitory effect of synthetic progestins, 4-MA and cyanoketone on human placental 3 beta-hydroxysteroid dehydrogenase/5----4-ene-isomerase activity. J Steroid Biochem Mol Biol. 1990 Oct;37(2):231-6. [PubMed:2268554 ]
Suzuki S, Endo Y, Tanaka S, Iizuka R: Indirect immunofluorescence studies on the steroid-producing activity of hamster ova. Am J Obstet Gynecol. 1984 Jan 1;148(1):76-85. [PubMed:6362415 ]
Duffy DM, Hess DL, Stouffer RL: Acute administration of a 3 beta-hydroxysteroid dehydrogenase inhibitor to rhesus monkeys at the midluteal phase of the menstrual cycle: evidence for possible autocrine regulation of the primate corpus luteum by progesterone. J Clin Endocrinol Metab. 1994 Dec;79(6):1587-94. [PubMed:7989460 ]
Mensah-Nyagan AG, Feuilloley M, Dupont E, Do-Rego JL, Leboulenger F, Pelletier G, Vaudry H: Immunocytochemical localization and biological activity of 3 beta-hydroxysteroid dehydrogenase in the central nervous system of the frog. J Neurosci. 1994 Dec;14(12):7306-18. [PubMed:7996177 ]
Igaz P, Tombol Z, Szabo PM, Liko I, Racz K: Steroid biosynthesis inhibitors in the therapy of hypercortisolism: theory and practice. Curr Med Chem. 2008;15(26):2734-47. [PubMed:18991633 ]

Showing metabocard for Trilostane (HMDB0015240)

MOL for HMDB0015240 (Trilostane)

3D MOL for HMDB0015240 (Trilostane)

3D SDF for HMDB0015240 (Trilostane)

3D-SDF for HMDB0015240 (Trilostane)

PDB for HMDB0015240 (Trilostane)

3D PDB for HMDB0015240 (Trilostane)

SMILES for HMDB0015240 (Trilostane)

INCHI for HMDB0015240 (Trilostane)

Structure for HMDB0015240 (Trilostane)

3D Structure for HMDB0015240 (Trilostane)

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