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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014838

Secondary Accession Numbers

HMDB14838

Metabolite Identification

Common Name

Eplerenone

Description

Eplerenone, an aldosterone receptor antagonist similar to spironolactone, has been shown to produce sustained increases in plasma renin and serum aldosterone, consistent with inhibition of the negative regulatory feedback of aldosterone on renin secretion. The resulting increased plasma renin activity and aldosterone circulating levels do not overcome the effects of eplerenone. Eplerenone selectively binds to recombinant human mineralocorticoid receptors relative to its binding to recombinant human glucocorticoid, progesterone and androgen receptors.

Structure

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


  Mrv0541 04191212142D          

 32 37  0  0  1  0            999 V2000
    9.3804   -5.1874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3762   -6.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0933   -5.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2303   -6.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2303   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466   -7.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466   -6.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6586   -6.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6550   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3677   -7.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0841   -7.2496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0841   -6.4263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0975   -4.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8067   -5.1978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8013   -6.0238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5853   -6.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0750   -5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5937   -4.9466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4180   -4.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6736   -4.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0072   -3.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3398   -4.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4585   -3.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7976   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7959   -8.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5130   -7.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2266   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5161   -7.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6512   -5.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3637   -6.8310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8013   -4.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7971   -6.8476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  7  4  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 14  1  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  2  3  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  6  0  0  0
 10 11  1  0  0  0  0
 20 23  2  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  6  0  0  0
  2  8  1  0  0  0  0
 24 25  2  0  0  0  0
  4  5  1  0  0  0  0
 24 26  1  0  0  0  0
  5  6  1  0  0  0  0
 26 27  1  0  0  0  0
  2 12  1  0  0  0  0
  5 28  2  0  0  0  0
 12 15  1  0  0  0  0
  8 29  1  1  0  0  0
 14 13  1  0  0  0  0
 12 30  1  1  0  0  0
 13  1  1  0  0  0  0
 14 31  1  1  0  0  0
  6  9  2  0  0  0  0
 15 32  1  6  0  0  0
M  END

HMDB0014838
     RDKit          3D
Eplerenone
 60 65  0  0  0  0  0  0  0  0999 V2000
   -0.6114    4.3829    1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    3.0217    1.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    2.6451   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    3.5399   -1.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    1.2279   -0.4269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8031    0.7413    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663   -0.6444    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -1.1072    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477   -2.4901    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9614   -2.8641    0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023   -3.4732   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -2.9482    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341   -1.5466   -0.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2146   -1.6290   -1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -0.9779    0.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7048   -1.0743    1.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404   -1.7726    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5794   -1.3305    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2224   -0.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7442   -0.7960   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    0.8856   -0.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3723    1.9352   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.6716   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.4768   -0.0666 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4785    0.9722    1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    0.3154    1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2565   -0.2640    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3881   -0.6557   -0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2990   -0.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345    0.3369   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3922    4.9323    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    4.8390    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    4.4578    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192    1.2608   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6805    1.4315    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    0.9226    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222   -0.4762    0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -4.4062    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -3.7813   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.8861    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -3.6066   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.8517   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -2.5983   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.6185   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -2.8824    0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -2.1666    0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743   -1.1028    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -1.6854   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.0317   -2.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -1.1748   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    1.1794    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    1.9211   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    2.9152   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773    2.5302   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    1.4119   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    0.7277    2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6462    2.0722    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5819    1.0386    1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200   -0.5180    2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3268    0.0889   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 21 30  1  0
 30  5  1  0
 13  7  1  0
 17 15  1  0
 24 19  1  0
 30 15  1  0
 24 29  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  6
  6 35  1  0
  6 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 30 60  1  6
M  END


  Mrv0541 04191212142D          

 32 37  0  0  1  0            999 V2000
    9.3804   -5.1874    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3762   -6.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0933   -5.5990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2303   -6.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2303   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466   -7.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466   -6.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6586   -6.4185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6550   -7.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3677   -7.6590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0841   -7.2496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0841   -6.4263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0975   -4.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8067   -5.1978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8013   -6.0238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5853   -6.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0750   -5.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5937   -4.9466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4180   -4.9476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6736   -4.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0072   -3.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3398   -4.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4585   -3.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7976   -7.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7959   -8.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5130   -7.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2266   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5161   -7.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6512   -5.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3637   -6.8310    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8013   -4.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7971   -6.8476    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  7  4  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 14  1  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  2  3  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  6  0  0  0
 10 11  1  0  0  0  0
 20 23  2  0  0  0  0
 11 12  1  0  0  0  0
 11 24  1  6  0  0  0
  2  8  1  0  0  0  0
 24 25  2  0  0  0  0
  4  5  1  0  0  0  0
 24 26  1  0  0  0  0
  5  6  1  0  0  0  0
 26 27  1  0  0  0  0
  2 12  1  0  0  0  0
  5 28  2  0  0  0  0
 12 15  1  0  0  0  0
  8 29  1  1  0  0  0
 14 13  1  0  0  0  0
 12 30  1  1  0  0  0
 13  1  1  0  0  0  0
 14 31  1  1  0  0  0
  6  9  2  0  0  0  0
 15 32  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0014838

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O6/c1-21-7-4-14(25)10-13(21)11-15(20(27)28-3)19-16-5-8-23(9-6-18(26)30-23)22(16,2)12-17-24(19,21)29-17/h10,15-17,19H,4-9,11-12H2,1-3H3/t15-,16+,17-,19+,21+,22+,23-,24-/m1/s1

> <INCHI_KEY>
JUKPWJGBANNWMW-VWBFHTRKSA-N

> <FORMULA>
C24H30O6

> <MOLECULAR_WEIGHT>
414.4914

> <EXACT_MASS>
414.204238692

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.79478208771363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1'R,2R,2'S,9'R,10'R,11'S,15'S,17'R)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0¹,¹⁷.0²,⁷.0¹¹,¹⁵]octadecan]-6'-ene-9'-carboxylate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
2.331412885333333

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.113572089829304

> <JCHEM_PKA_STRONGEST_BASIC>
-4.183612891330253

> <JCHEM_POLAR_SURFACE_AREA>
82.19999999999999

> <JCHEM_REFRACTIVITY>
106.67769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eplerenone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014838
     RDKit          3D
Eplerenone
 60 65  0  0  0  0  0  0  0  0999 V2000
   -0.6114    4.3829    1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    3.0217    1.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    2.6451   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    3.5399   -1.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    1.2279   -0.4269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8031    0.7413    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663   -0.6444    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -1.1072    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477   -2.4901    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9614   -2.8641    0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023   -3.4732   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -2.9482    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341   -1.5466   -0.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2146   -1.6290   -1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -0.9779    0.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7048   -1.0743    1.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404   -1.7726    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5794   -1.3305    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2224   -0.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7442   -0.7960   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    0.8856   -0.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3723    1.9352   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.6716   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.4768   -0.0666 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4785    0.9722    1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    0.3154    1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2565   -0.2640    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3881   -0.6557   -0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2990   -0.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345    0.3369   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3922    4.9323    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    4.8390    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    4.4578    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192    1.2608   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6805    1.4315    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    0.9226    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222   -0.4762    0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -4.4062    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -3.7813   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.8861    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -3.6066   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.8517   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -2.5983   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.6185   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -2.8824    0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -2.1666    0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743   -1.1028    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -1.6854   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.0317   -2.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -1.1748   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    1.1794    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    1.9211   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    2.9152   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773    2.5302   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    1.4119   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    0.7277    2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6462    2.0722    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5819    1.0386    1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200   -0.5180    2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3268    0.0889   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 21 30  1  0
 30  5  1  0
 13  7  1  0
 17 15  1  0
 24 19  1  0
 30 15  1  0
 24 29  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  6
  6 35  1  0
  6 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 30 60  1  6
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      17.510  -9.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.502 -11.223   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      18.841 -10.451   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      13.497 -11.981   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.497 -13.521   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.834 -14.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.834 -11.211   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.163 -11.981   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.156 -13.521   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.486 -14.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.824 -13.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.824 -11.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.849  -8.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.173  -9.703   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.162 -11.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.626 -11.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.540 -10.489   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.642  -9.234   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      23.180  -9.236   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      23.657  -7.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.413  -6.867   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.168  -7.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      25.123  -7.298   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.156 -14.305   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.152 -15.845   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      21.491 -13.538   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      22.823 -14.311   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.163 -14.292   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.149 -10.441   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      17.479 -12.751   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0      20.162  -8.162   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      20.155 -12.782   0.000  0.00  0.00           H+0
CONECT    1    2    3   13                                                  
CONECT    2    1    3    8   12                                             
CONECT    3    1    2                                                       
CONECT    4    7    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    9                                                       
CONECT    7    8    4                                                       
CONECT    8    7    9    2   29                                             
CONECT    9    8   10    6                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11    2   15   30                                             
CONECT   13   14    1                                                       
CONECT   14   15   18   13   31                                             
CONECT   15   14   16   12   32                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19   22                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   18                                                       
CONECT   23   20                                                            
CONECT   24   11   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28    5                                                            
CONECT   29    8                                                            
CONECT   30   12                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

COMPND    HMDB0014838
HETATM    1  C1  UNL     1      -0.611   4.383   1.434  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.956   3.022   1.132  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.359   2.645  -0.139  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.410   3.540  -1.011  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.711   1.228  -0.427  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.803   0.741   0.499  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.166  -0.644   0.221  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.369  -1.107   0.510  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.748  -2.490   0.239  1.00  0.00           C  
HETATM   10  O3  UNL     1      -5.961  -2.864   0.281  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.702  -3.473  -0.090  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.335  -2.948   0.163  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.134  -1.547  -0.393  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.215  -1.629  -1.874  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.808  -0.978   0.101  1.00  0.00           C  
HETATM   16  O4  UNL     1      -0.705  -1.074   1.492  1.00  0.00           O  
HETATM   17  C13 UNL     1       0.140  -1.773   0.657  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.579  -1.330   0.769  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.801  -0.222  -0.179  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.744  -0.796  -1.595  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.765   0.886  -0.034  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.372   1.935  -0.929  1.00  0.00           C  
HETATM   23  C19 UNL     1       2.869   1.672  -0.991  1.00  0.00           C  
HETATM   24  C20 UNL     1       3.117   0.477  -0.067  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.479   0.972   1.270  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.824   0.315   1.544  1.00  0.00           C  
HETATM   27  C23 UNL     1       5.256  -0.264   0.251  1.00  0.00           C  
HETATM   28  O5  UNL     1       6.388  -0.656  -0.058  1.00  0.00           O  
HETATM   29  O6  UNL     1       4.153  -0.299  -0.589  1.00  0.00           O  
HETATM   30  C24 UNL     1      -0.535   0.337  -0.554  1.00  0.00           C  
HETATM   31  H1  UNL     1      -0.392   4.932   0.488  1.00  0.00           H  
HETATM   32  H2  UNL     1      -1.546   4.839   1.831  1.00  0.00           H  
HETATM   33  H3  UNL     1       0.171   4.458   2.186  1.00  0.00           H  
HETATM   34  H4  UNL     1      -2.219   1.261  -1.440  1.00  0.00           H  
HETATM   35  H5  UNL     1      -3.680   1.431   0.332  1.00  0.00           H  
HETATM   36  H6  UNL     1      -2.541   0.923   1.569  1.00  0.00           H  
HETATM   37  H7  UNL     1      -5.122  -0.476   0.961  1.00  0.00           H  
HETATM   38  H8  UNL     1      -3.841  -4.406   0.503  1.00  0.00           H  
HETATM   39  H9  UNL     1      -3.883  -3.781  -1.144  1.00  0.00           H  
HETATM   40  H10 UNL     1      -2.178  -2.886   1.254  1.00  0.00           H  
HETATM   41  H11 UNL     1      -1.602  -3.607  -0.344  1.00  0.00           H  
HETATM   42  H12 UNL     1      -2.838  -0.852  -2.358  1.00  0.00           H  
HETATM   43  H13 UNL     1      -2.651  -2.598  -2.234  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.189  -1.619  -2.295  1.00  0.00           H  
HETATM   45  H15 UNL     1       0.030  -2.882   0.722  1.00  0.00           H  
HETATM   46  H16 UNL     1       2.276  -2.167   0.500  1.00  0.00           H  
HETATM   47  H17 UNL     1       1.774  -1.103   1.823  1.00  0.00           H  
HETATM   48  H18 UNL     1       1.108  -1.685  -1.648  1.00  0.00           H  
HETATM   49  H19 UNL     1       1.572  -0.032  -2.358  1.00  0.00           H  
HETATM   50  H20 UNL     1       2.792  -1.175  -1.796  1.00  0.00           H  
HETATM   51  H21 UNL     1       0.665   1.179   1.011  1.00  0.00           H  
HETATM   52  H22 UNL     1       0.994   1.921  -1.955  1.00  0.00           H  
HETATM   53  H23 UNL     1       1.275   2.915  -0.424  1.00  0.00           H  
HETATM   54  H24 UNL     1       3.477   2.530  -0.681  1.00  0.00           H  
HETATM   55  H25 UNL     1       3.190   1.412  -2.027  1.00  0.00           H  
HETATM   56  H26 UNL     1       2.779   0.728   2.083  1.00  0.00           H  
HETATM   57  H27 UNL     1       3.646   2.072   1.320  1.00  0.00           H  
HETATM   58  H28 UNL     1       5.582   1.039   1.867  1.00  0.00           H  
HETATM   59  H29 UNL     1       4.720  -0.518   2.262  1.00  0.00           H  
HETATM   60  H30 UNL     1      -0.327   0.089  -1.643  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   30   34
CONECT    6    7   35   36
CONECT    7    8    8   13
CONECT    8    9   37
CONECT    9   10   10   11
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   15
CONECT   14   42   43   44
CONECT   15   16   17   30
CONECT   16   17
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   21   24
CONECT   20   48   49   50
CONECT   21   22   30   51
CONECT   22   23   52   53
CONECT   23   24   54   55
CONECT   24   25   29
CONECT   25   26   56   57
CONECT   26   27   58   59
CONECT   27   28   28   29
CONECT   30   60
END

HMDB0014838
     RDKit          3D
Eplerenone
 60 65  0  0  0  0  0  0  0  0999 V2000
   -0.6114    4.3829    1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563    3.0217    1.1317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    2.6451   -0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099    3.5399   -1.0107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    1.2279   -0.4269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8031    0.7413    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1663   -0.6444    0.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3687   -1.1072    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477   -2.4901    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9614   -2.8641    0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7023   -3.4732   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -2.9482    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341   -1.5466   -0.3928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2146   -1.6290   -1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -0.9779    0.1006 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7048   -1.0743    1.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1404   -1.7726    0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5794   -1.3305    0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005   -0.2224   -0.1793 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7442   -0.7960   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    0.8856   -0.0336 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3723    1.9352   -0.9291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    1.6716   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.4768   -0.0666 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4785    0.9722    1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237    0.3154    1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2565   -0.2640    0.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3881   -0.6557   -0.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2990   -0.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345    0.3369   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3922    4.9323    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    4.8390    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    4.4578    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192    1.2608   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6805    1.4315    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    0.9226    1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1222   -0.4762    0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412   -4.4062    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -3.7813   -1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.8861    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017   -3.6066   -0.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -0.8517   -2.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6510   -2.5983   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1894   -1.6185   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -2.8824    0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -2.1666    0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7743   -1.1028    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1083   -1.6854   -1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.0317   -2.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915   -1.1748   -1.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6647    1.1794    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    1.9211   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751    2.9152   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773    2.5302   -0.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    1.4119   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7793    0.7277    2.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6462    2.0722    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5819    1.0386    1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200   -0.5180    2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3268    0.0889   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 21 30  1  0
 30  5  1  0
 13  7  1  0
 17 15  1  0
 24 19  1  0
 30 15  1  0
 24 29  1  6
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  6
  6 35  1  0
  6 36  1  0
  8 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 30 60  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Epoxymexrenone	ChEBI
Inspra	ChEBI
9,11-Epoxy-7-(methoxycarbonyl)-3-oxo-17-pregn-4-ene-21,17-carbolactone	HMDB
Eplerenon	HMDB

Chemical Formula

C₂₄H₃₀O₆

Average Molecular Weight

414.4914

Monoisotopic Molecular Weight

414.204238692

IUPAC Name

methyl (1'R,2R,2'S,9'R,10'R,11'S,15'S,17'R)-2',15'-dimethyl-5,5'-dioxo-18'-oxaspiro[oxolane-2,14'-pentacyclo[8.8.0.0¹,¹⁷.0²,⁷.0¹¹,¹⁵]octadecan]-6'-ene-9'-carboxylate

Traditional Name

eplerenone

CAS Registry Number

107724-20-9

SMILES

[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC

InChI Identifier

InChI=1S/C24H30O6/c1-21-7-4-14(25)10-13(21)11-15(20(27)28-3)19-16-5-8-23(9-6-18(26)30-23)22(16,2)12-17-24(19,21)29-17/h10,15-17,19H,4-9,11-12H2,1-3H3/t15-,16+,17-,19+,21+,22+,23-,24-/m1/s1

InChI Key

JUKPWJGBANNWMW-VWBFHTRKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as spironolactones and derivatives. These are steroid lactones with a structure based on the spironolactone skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Spironolactones and derivatives

Alternative Parents

Substituents

Spironolactone
Cyclohexenone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Methyl ester
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Carboxylic acid derivative
Ether
Oxirane
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:31547 )
epoxide (CHEBI:31547 )
methyl ester (CHEBI:31547 )
gamma-lactone (CHEBI:31547 )
oxaspiro compound (CHEBI:31547 )
steroid acid ester (CHEBI:31547 )

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

Membrane (HMDB: HMDB0014838)
Extracellular (HMDB: HMDB0014838)

Source

Exogenous

Exogenous (HMDB: HMDB0014838)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Eplerenone Action Pathway (PathBank: SMP0000135)

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	0.009 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	197.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.009 g/L	ALOGPS
logP	1.67	ALOGPS
logP	2.33	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	15.11	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	106.68 m³·mol⁻¹	ChemAxon
Polarizability	43.79 Å³	ChemAxon
Number of Rings	6	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
DarkChem	[M+H]+	196.582	31661259
DarkChem	[M-H]-	193.952	31661259
DeepCCS	[M-2H]-	230.273	30932474
DeepCCS	[M+Na]+	204.367	30932474
AllCCS	[M+H]+	199.6	32859911
AllCCS	[M+H-H2O]+	197.3	32859911
AllCCS	[M+NH4]+	201.7	32859911
AllCCS	[M+Na]+	202.3	32859911
AllCCS	[M-H]-	204.2	32859911
AllCCS	[M+Na-2H]-	204.8	32859911
AllCCS	[M+HCOO]-	205.5	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.	7.11 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8052 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2845.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	208.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	207.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	145.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	709.8 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	622.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	458.0 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	1455.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	432.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	301.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.0 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	48.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eplerenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC	4484.4	Standard polar	33892256
Eplerenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC	3085.7	Standard non polar	33892256
Eplerenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)C[C@H]1O[C@@]11[C@@]2([H])[C@@H](CC2=CC(=O)CC[C@]12C)C(=O)OC	3610.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eplerenone,1TMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3258.3	Semi standard non polar	33892256
Eplerenone,1TMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3173.0	Standard non polar	33892256
Eplerenone,1TMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3874.4	Standard polar	33892256
Eplerenone,1TBDMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3481.6	Semi standard non polar	33892256
Eplerenone,1TBDMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3404.3	Standard non polar	33892256
Eplerenone,1TBDMS,isomer #1	COC(=O)[C@@H]1CC2=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]2(C)[C@@]23O[C@@H]2C[C@@]2(C)[C@@H](CC[C@@]24CCC(=O)O4)[C@H]13	3997.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eplerenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adu-0209000000-12b60f587e43aa45d6d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eplerenone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 10V, Positive-QTOF	splash10-014i-0009400000-ea48b83fadcea11b59c4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 20V, Positive-QTOF	splash10-0aos-0109000000-7c2b34b32e47c8b99347	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 40V, Positive-QTOF	splash10-0a4i-4955000000-4a2bd122f48c88a31213	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 10V, Negative-QTOF	splash10-03di-0006900000-58cc006a22b6e44336a4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 20V, Negative-QTOF	splash10-03xr-0009400000-8706c8ed2bc60109596e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 40V, Negative-QTOF	splash10-0006-7019000000-4c8e14c579aa065c04c9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 10V, Positive-QTOF	splash10-014i-0001900000-0eaf4de79ce0afc4b997	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 20V, Positive-QTOF	splash10-014i-0119300000-db12e4174bf5f8367cd5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 40V, Positive-QTOF	splash10-00kb-1329000000-ac3a3b5b248711145827	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 10V, Negative-QTOF	splash10-03di-0003900000-5fb3fe537cffeaf693e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 20V, Negative-QTOF	splash10-03di-0007900000-431de4fbbae9c6ab1882	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eplerenone 40V, Negative-QTOF	splash10-014i-0009000000-e64b0b7d685ef47232f3	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Eplerenone Action Pathway		Not Available

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 DB00700	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00700	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00700

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10203511

KEGG Compound ID

C12512

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eplerenone

METLIN ID

Not Available

PubChem Compound

443872

PDB ID

Not Available

ChEBI ID

31547

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

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. 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

2. 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

Enzyme Details

3. Cytochrome P450 3A7

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:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

4. Mineralocorticoid receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:: NR3C2
Uniprot ID:: P08235
Molecular weight:: 107066.6

References

Moore TD, Nawarskas JJ, Anderson JR: Eplerenone: a selective aldosterone receptor antagonist for hypertension and heart failure. Heart Dis. 2003 Sep-Oct;5(5):354-63. [PubMed:14503934 ]
Fraccarollo D, Galuppo P, Hildemann S, Christ M, Ertl G, Bauersachs J: Additive improvement of left ventricular remodeling and neurohormonal activation by aldosterone receptor blockade with eplerenone and ACE inhibition in rats with myocardial infarction. J Am Coll Cardiol. 2003 Nov 5;42(9):1666-73. [PubMed:14607457 ]
Rogerson FM, Yao Y, Smith BJ, Fuller PJ: Differences in the determinants of eplerenone, spironolactone and aldosterone binding to the mineralocorticoid receptor. Clin Exp Pharmacol Physiol. 2004 Oct;31(10):704-9. [PubMed:15554912 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

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 Eplerenone (HMDB0014838)

MOL for HMDB0014838 (Eplerenone)

3D MOL for HMDB0014838 (Eplerenone)

3D SDF for HMDB0014838 (Eplerenone)

3D-SDF for HMDB0014838 (Eplerenone)

PDB for HMDB0014838 (Eplerenone)

3D PDB for HMDB0014838 (Eplerenone)

SMILES for HMDB0014838 (Eplerenone)

INCHI for HMDB0014838 (Eplerenone)

Structure for HMDB0014838 (Eplerenone)

3D Structure for HMDB0014838 (Eplerenone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References