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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 15:12:27 UTC

Update Date

2021-09-14 15:40:02 UTC

HMDB ID

HMDB0003033

Secondary Accession Numbers

HMDB03033

Metabolite Identification

Common Name

Canrenone

Description

Canrenone is the major metabolite of spironolactone. Spironolactone is a competitive aldosterone receptor antagonist (ARA), has traditionally been the treatment of first choice in idiopathic hyperaldosteronism (IHA) and for preoperative management of aldosterone producing adenoma (APA), and its therapeutic properties are attributable to active metabolite canrenone. Canrenone and the K+ salt of canrenoate are also in clinical use: they avoid the formation of intermediate products with anti-androgenic and progestational actions, resulting in a decreased incidence of side effects. (PMID:10790593 ).

Structure

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


  Mrv1652305271900052D          

 28 32  0  0  1  0            999 V2000
   28.3116  -15.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4525  -16.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7074   -9.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6636  -14.4176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.9490  -14.0051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.4910  -15.2193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.9490  -13.1801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.6636  -12.7676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.3780  -14.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3410  -14.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6752  -15.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3780  -13.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6768  -11.9083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.3180  -16.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4760  -14.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1983  -12.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9359  -11.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4621  -11.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0318  -16.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3881  -12.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1917  -11.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6458  -15.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4760  -10.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9290  -10.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7042  -10.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3458  -13.7374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.3800  -13.5144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.2376  -12.4420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  1 22  1  0  0  0  0
  2 22  2  0  0  0  0
  3 25  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 26  1  6  0  0  0
  6 11  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 27  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 28  1  6  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 20  1  1  0  0  0
 14 19  1  0  0  0  0
 16 21  2  0  0  0  0
 17 21  1  0  0  0  0
 17 24  2  0  0  0  0
 18 23  1  0  0  0  0
 19 22  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

HMDB0003033
     RDKit          3D
Canrenone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -1.7934    1.5450    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.3371    0.4525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2083   -0.8555    1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.0062    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4015   -0.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4040    0.9430   -0.3610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1352    1.7659   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.6281   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592    0.6423   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4781    0.5741   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698   -0.3937    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -0.1889    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939   -1.6712    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.6687   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -0.3327    0.2307 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7663    0.0791    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863    0.6388   -0.8278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7524    1.7283   -1.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967    1.4069   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1243    0.1701   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2930   -1.0236   -1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181   -1.7983   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355   -0.7559    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3536   -0.7401    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    0.1848    0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926    1.3968    2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    1.7710    1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401    2.4642    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7692    0.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.7891    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -0.5869    2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -2.1157    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -1.0670   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    1.4840    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.5232   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806    2.2693   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    1.2787   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -2.4611   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -1.9265    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.9448   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -2.4855    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7149   -0.7398    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    0.5317    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.9197    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9600   -0.2391   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    2.7533   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    1.6710   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2722   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842    1.1747   -1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836   -0.7731   -2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4095   -1.6415   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1471   -2.1945   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.5831    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 17  2  1  0
 20 25  1  1
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  8 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
M  END


  Mrv1652305271900052D          

 28 32  0  0  1  0            999 V2000
   28.3116  -15.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4525  -16.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7074   -9.3053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6636  -14.4176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.9490  -14.0051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.4910  -15.2193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.9490  -13.1801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.6636  -12.7676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.3780  -14.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3410  -14.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6752  -15.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3780  -13.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6768  -11.9083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.3180  -16.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4760  -14.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1983  -12.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9359  -11.4729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4621  -11.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0318  -16.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3881  -12.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1917  -11.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6458  -15.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4760  -10.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9290  -10.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7042  -10.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3458  -13.7374    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.3800  -13.5144    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.2376  -12.4420    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  1 22  1  0  0  0  0
  2 22  2  0  0  0  0
  3 25  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 26  1  6  0  0  0
  6 11  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  7 27  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 28  1  6  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 20  1  1  0  0  0
 14 19  1  0  0  0  0
 16 21  2  0  0  0  0
 17 21  1  0  0  0  0
 17 24  2  0  0  0  0
 18 23  1  0  0  0  0
 19 22  1  0  0  0  0
 23 25  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003033

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1

> <INCHI_KEY>
UJVLDDZCTMKXJK-WNHSNXHDSA-N

> <FORMULA>
C22H28O3

> <MOLECULAR_WEIGHT>
340.4559

> <EXACT_MASS>
340.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.669085243856564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.595398729

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.93862843295016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.771554231331754

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
97.48279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003033
     RDKit          3D
Canrenone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -1.7934    1.5450    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.3371    0.4525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2083   -0.8555    1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.0062    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4015   -0.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4040    0.9430   -0.3610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1352    1.7659   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.6281   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592    0.6423   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4781    0.5741   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698   -0.3937    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -0.1889    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939   -1.6712    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.6687   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -0.3327    0.2307 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7663    0.0791    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863    0.6388   -0.8278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7524    1.7283   -1.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967    1.4069   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1243    0.1701   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2930   -1.0236   -1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181   -1.7983   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355   -0.7559    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3536   -0.7401    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    0.1848    0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926    1.3968    2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    1.7710    1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401    2.4642    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7692    0.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.7891    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -0.5869    2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -2.1157    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -1.0670   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    1.4840    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.5232   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806    2.2693   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    1.2787   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -2.4611   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -1.9265    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.9448   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -2.4855    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7149   -0.7398    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    0.5317    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.9197    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9600   -0.2391   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    2.7533   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    1.6710   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2722   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842    1.1747   -1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836   -0.7731   -2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4095   -1.6415   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1471   -2.1945   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.5831    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 17  2  1  0
 20 25  1  1
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  8 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      52.848 -28.251   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      54.978 -29.982   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.720 -17.370   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      51.639 -26.913   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      50.305 -26.143   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.317 -28.409   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.305 -24.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      51.639 -23.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      52.972 -26.143   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      49.170 -27.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.794 -28.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.972 -24.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.663 -22.229   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      50.994 -29.915   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      53.155 -27.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.903 -23.822   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.280 -21.416   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      53.129 -21.427   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      52.326 -30.687   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      52.991 -23.009   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      48.891 -22.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      53.472 -29.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      53.155 -19.756   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      50.267 -19.745   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      51.715 -18.910   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      49.179 -25.643   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      49.243 -25.227   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      52.710 -23.225   0.000  0.00  0.00           H+0
CONECT    1    6   22                                                       
CONECT    2   22                                                            
CONECT    3   25                                                            
CONECT    4    5    6    9   15                                             
CONECT    5    4    7   10   26                                             
CONECT    6    1    4   11   14                                             
CONECT    7    5    8   16   27                                             
CONECT    8    7   12   13   28                                             
CONECT    9    4   12                                                       
CONECT   10    5   11                                                       
CONECT   11    6   10                                                       
CONECT   12    8    9                                                       
CONECT   13    8   17   18   20                                             
CONECT   14    6   19                                                       
CONECT   15    4                                                            
CONECT   16    7   21                                                       
CONECT   17   13   21   24                                                  
CONECT   18   13   23                                                       
CONECT   19   14   22                                                       
CONECT   20   13                                                            
CONECT   21   16   17                                                       
CONECT   22    1    2   19                                                  
CONECT   23   18   25                                                       
CONECT   24   17   25                                                       
CONECT   25    3   23   24                                                  
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

COMPND    HMDB0003033
HETATM    1  C1  UNL     1      -1.793   1.545   1.349  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.773   0.337   0.452  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.208  -0.855   1.136  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.255  -1.006   1.112  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.002  -0.402  -0.035  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.404   0.943  -0.361  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.135   1.766  -1.306  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.435   1.628  -1.454  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.159   0.642  -0.668  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.478   0.574  -0.723  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.270  -0.394   0.041  1.00  0.00           C  
HETATM   12  O1  UNL     1       6.430  -0.189   0.401  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.594  -1.671   0.372  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.141  -1.669  -0.016  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.477  -0.333   0.231  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.766   0.079   1.652  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.986   0.639  -0.828  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.752   1.728  -1.424  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.197   1.407  -1.058  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.124   0.170  -0.149  1.00  0.00           C  
HETATM   21  C20 UNL     1      -3.293  -1.024  -1.019  1.00  0.00           C  
HETATM   22  C21 UNL     1      -4.418  -1.798  -0.338  1.00  0.00           C  
HETATM   23  C22 UNL     1      -5.135  -0.756   0.474  1.00  0.00           C  
HETATM   24  O2  UNL     1      -6.354  -0.740   0.794  1.00  0.00           O  
HETATM   25  O3  UNL     1      -4.168   0.185   0.796  1.00  0.00           O  
HETATM   26  H1  UNL     1      -1.193   1.397   2.279  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.834   1.771   1.720  1.00  0.00           H  
HETATM   28  H3  UNL     1      -1.440   2.464   0.871  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.740  -1.769   0.756  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.532  -0.789   2.216  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.707  -0.587   2.059  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.477  -2.116   1.079  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.847  -1.067  -0.917  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.340   1.484   0.631  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.628   2.523  -1.923  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.981   2.269  -2.185  1.00  0.00           H  
HETATM   37  H12 UNL     1       4.999   1.279  -1.373  1.00  0.00           H  
HETATM   38  H13 UNL     1       5.096  -2.461  -0.225  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.759  -1.926   1.438  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.032  -1.945  -1.093  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.645  -2.486   0.555  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.715  -0.740   2.375  1.00  0.00           H  
HETATM   43  H18 UNL     1       3.784   0.532   1.768  1.00  0.00           H  
HETATM   44  H19 UNL     1       2.070   0.920   1.931  1.00  0.00           H  
HETATM   45  H20 UNL     1      -0.960  -0.239  -1.468  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.472   2.753  -1.152  1.00  0.00           H  
HETATM   47  H22 UNL     1      -1.662   1.671  -2.547  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.588   2.272  -0.494  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.784   1.175  -1.950  1.00  0.00           H  
HETATM   50  H25 UNL     1      -3.684  -0.773  -2.039  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.410  -1.641  -1.166  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.147  -2.194  -1.065  1.00  0.00           H  
HETATM   53  H28 UNL     1      -3.979  -2.583   0.287  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   17   20
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   15   33
CONECT    6    7   17   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   10   15
CONECT   10   11   37
CONECT   11   12   12   13
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   25
CONECT   21   22   50   51
CONECT   22   23   52   53
CONECT   23   24   24   25
END

HMDB0003033
     RDKit          3D
Canrenone
 53 57  0  0  0  0  0  0  0  0999 V2000
   -1.7934    1.5450    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731    0.3371    0.4525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2083   -0.8555    1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.0062    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0025   -0.4015   -0.0346 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4040    0.9430   -0.3610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1352    1.7659   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    1.6281   -1.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1592    0.6423   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4781    0.5741   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2698   -0.3937    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -0.1889    0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5939   -1.6712    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.6687   -0.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -0.3327    0.2307 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7663    0.0791    1.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863    0.6388   -0.8278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7524    1.7283   -1.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1967    1.4069   -1.0582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1243    0.1701   -0.1491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2930   -1.0236   -1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181   -1.7983   -0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1355   -0.7559    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3536   -0.7401    0.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682    0.1848    0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926    1.3968    2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    1.7710    1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401    2.4642    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7692    0.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5318   -0.7891    2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -0.5869    2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770   -2.1157    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -1.0670   -0.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3404    1.4840    0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.5232   -1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9806    2.2693   -2.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9986    1.2787   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958   -2.4611   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7588   -1.9265    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.9448   -1.0934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6453   -2.4855    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7149   -0.7398    2.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7842    0.5317    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697    0.9197    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9600   -0.2391   -1.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    2.7533   -1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624    1.6710   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.2722   -0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842    1.1747   -1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836   -0.7731   -2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4095   -1.6415   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1471   -2.1945   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9787   -2.5831    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 17  2  1  0
 20 25  1  1
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  8 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aldadiene	MeSH
Phanurane	MeSH
R.P., 11614	MeSH
SC-9376Canrenone	ChEMBL, HMDB
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone	HMDB
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactone	HMDB
17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone	HMDB
17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid	HMDB
20-Spiroxa-4,6-diene-3,21-dione	HMDB
3'-(3-oxo-17b-Hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone	HMDB
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone	HMDB
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactone	HMDB
3-(3-oxo-17b-Hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone	HMDB

Chemical Formula

C₂₂H₂₈O₃

Average Molecular Weight

340.4559

Monoisotopic Molecular Weight

340.203844762

IUPAC Name

(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

Traditional Name

(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione

CAS Registry Number

976-71-6

SMILES

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

InChI Identifier

InChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1

InChI Key

UJVLDDZCTMKXJK-WNHSNXHDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
3-oxosteroid
Oxosteroid
Cyclohexenone
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 6831747)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003033)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0003033)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003033)

Source

Exogenous

Exogenous (HMDB: HMDB0003033)

Food

Food (HMDB: HMDB0003033)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0003033)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003033)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003033)

Lipid metabolism pathway (HMDB: HMDB0003033)

Cellular process

Cell signaling (HMDB: HMDB0003033)

Biochemical process

Lipid transport (HMDB: HMDB0003033)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003033)

Molecular messenger

Signaling molecule (HMDB: HMDB0003033)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003033)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003033)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.68	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	2.79	ALOGPS
logP	3.6	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	19.94	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	97.48 m³·mol⁻¹	ChemAxon
Polarizability	38.67 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
DarkChem	[M+H]+	182.129	31661259
DarkChem	[M-H]-	175.97	31661259
DeepCCS	[M-2H]-	217.427	30932474
DeepCCS	[M+Na]+	192.383	30932474
AllCCS	[M+H]+	186.6	32859911
AllCCS	[M+H-H2O]+	183.8	32859911
AllCCS	[M+NH4]+	189.2	32859911
AllCCS	[M+Na]+	189.9	32859911
AllCCS	[M-H]-	192.6	32859911
AllCCS	[M+Na-2H]-	192.7	32859911
AllCCS	[M+HCOO]-	193.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.02 minutes	32390414
Predicted by Siyang on May 30, 2022	19.3592 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2946.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	517.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	240.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	517.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	814.0 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	810.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1678.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	510.0 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	1554.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	609.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	578.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Canrenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3800.8	Standard polar	33892256
Canrenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	2815.2	Standard non polar	33892256
Canrenone	[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C	3292.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Canrenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O1	3127.4	Semi standard non polar	33892256
Canrenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O1	2924.3	Standard non polar	33892256
Canrenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O1	3471.4	Standard polar	33892256
Canrenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3368.8	Semi standard non polar	33892256
Canrenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3163.3	Standard non polar	33892256
Canrenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3655.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Canrenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01u0-0294000000-4ef8f41e0a3349fc5759	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Canrenone 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 - Canrenone LC-ESI-ITFT , positive-QTOF	splash10-0a4j-2910000000-895da7d842991e1f2631	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-3900000000-44a9709cabb5e8f1da5d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOF	splash10-0079-0962000000-d3aa34556f83b16405c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOF	splash10-05tr-0962000000-924d636ff93f46fb7ccc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 80V, Positive-QTOF	splash10-0a4i-3900000000-3a30ad26d169f0f4376d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 35V, Positive-QTOF	splash10-0079-0952000000-a659329c1d4dbdaa35fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 55V, Positive-QTOF	splash10-0a4j-2910000000-2271fd51503b36f1ecaf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOF	splash10-0a4i-4900000000-849841b26aeae34c6f44	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOF	splash10-0006-1519000000-065659f87f49131d9fab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOF	splash10-0a4i-4900000000-fb528a0adb13d3312a17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOF	splash10-0006-0009000000-6bba4c38ef31d75b00ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOF	splash10-0006-0009000000-66e37b861f6b28f50cf2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOF	splash10-0006-1619000000-c577e8993bba997d0aab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Canrenone 55V, Positive-QTOF	splash10-05tr-0962000000-aca4c3d2f6a79f56a8fc	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOF	splash10-0006-0069000000-abaf24a61a9edc70752d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOF	splash10-00rx-0092000000-2761d2c9cf7170266c03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOF	splash10-0fsr-1970000000-540279571f8d029740a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 10V, Negative-QTOF	splash10-000i-0029000000-f3a98fb00ac173fe1bf3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 20V, Negative-QTOF	splash10-000j-0069000000-c492d9b48fd5165300ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 40V, Negative-QTOF	splash10-0006-5090000000-08c680b27aee962071d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOF	splash10-0006-0009000000-0e4e8b92f10e785e2dde	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOF	splash10-004l-0943000000-4f159ad08076205f9bef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOF	splash10-03mi-1910000000-72c9aebfc155facc9fb8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 10V, Negative-QTOF	splash10-000i-0009000000-0b542547fa4ff7747c31	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Canrenone 20V, Negative-QTOF	splash10-000i-1059000000-1afc199ac4c118cab55c	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	6831747	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12221

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023096

KNApSAcK ID

Not Available

Chemspider ID

13192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Canrenone

METLIN ID

Not Available

PubChem Compound

13789

PDB ID

Not Available

ChEBI ID

987229

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Skibinska, Maria; Smolinska, Jadwiga; Stochlak, Edward. Method of manufacturing canrenone. Pol. (1994), 4 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Deventer K, Van Eenoo P, Delbeke FT: Simultaneous determination of beta-blocking agents and diuretics in doping analysis by liquid chromatography/mass spectrometry with scan-to-scan polarity switching. Rapid Commun Mass Spectrom. 2005;19(2):90-8. [PubMed:15584083 ]
Mantero F, Lucarelli G: Aldosterone antagonists in hypertension and heart failure. Ann Endocrinol (Paris). 2000 Feb;61(1):52-60. [PubMed:10790593 ]

Showing metabocard for Canrenone (HMDB0003033)

MOL for HMDB0003033 (Canrenone)

3D MOL for HMDB0003033 (Canrenone)

3D SDF for HMDB0003033 (Canrenone)

3D-SDF for HMDB0003033 (Canrenone)

PDB for HMDB0003033 (Canrenone)

3D PDB for HMDB0003033 (Canrenone)

SMILES for HMDB0003033 (Canrenone)

INCHI for HMDB0003033 (Canrenone)

Structure for HMDB0003033 (Canrenone)

3D Structure for HMDB0003033 (Canrenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra