NP-MRD: Showing NP-Card for Canrenone (NP0000985)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:27 UTC

Updated at

2024-09-17 15:43:41 UTC

NP-MRD ID

NP0000985

Secondary Accession Numbers

None

Natural Product 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>
NP0000985

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

Synonyms

Value	Source
SC-9376Canrenone	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
Aldadiene	HMDB
Phanurane	HMDB
R.P., 11614	HMDB

Chemical Formula

C₂₂H₂₈O₃

Average Mass

340.4559 Da

Monoisotopic Mass

340.20384 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Solid

Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0003033

DrugBank ID

DB12221

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Mantero F, Lucarelli G: Aldosterone antagonists in hypertension and heart failure. Ann Endocrinol (Paris). 2000 Feb;61(1):52-60. [PubMed:10790593 ]
Tatipalli M, Siripuram VK, Long T, Shuster D, Bernstein G, Martineau P, Cook KA, Cristofoletti R, Schmidt S, Vozmediano V: Model-Informed Optimization of a Pediatric Clinical Pharmacokinetic Trial of a New Spironolactone Liquid Formulation. Pharmaceutics. 2021 Jun 8;13(6). pii: pharmaceutics13060849. doi: 10.3390/pharmaceutics13060849. [PubMed:34201093 ]
Dahmana N, Mugnier T, Gabriel D, Favez T, Kowalczuk L, Behar-Cohen F, Gurny R, Kalia YN: Polymeric micelle mediated follicular delivery of spironolactone: Targeting the mineralocorticoid receptor to prevent glucocorticoid-induced activation and delayed cutaneous wound healing. Int J Pharm. 2021 Jul 15;604:120773. doi: 10.1016/j.ijpharm.2021.120773. Epub 2021 Jun 4. [PubMed:34090990 ]
Young MJ, Kanki M, Karthigan N, Konstandopoulos P: The role of the mineralocorticoid receptor and mineralocorticoid-receptor-directed therapies in heart failure. Endocrinology. 2021 May 29. pii: 6288445. doi: 10.1210/endocr/bqab105. [PubMed:34050730 ]
Cha J, Hong S, Lee J, Gwak J, Kim M, Kim T, Hur J, Giesy JP, Khim JS: Novel polar AhR-active chemicals detected in sediments of an industrial area using effect-directed analysis based on in vitro bioassays with full-scan high resolution mass spectrometric screening. Sci Total Environ. 2021 Jul 20;779:146566. doi: 10.1016/j.scitotenv.2021.146566. Epub 2021 Mar 17. [PubMed:34030261 ]
Rong S, Tang X, Guan S, Zhang B, Li Q, Cai B, Huang J: Effects of Impeller Geometry on the 11alpha-Hydroxylation of Canrenone in Rushton Turbine-Stirred Tanks. J Microbiol Biotechnol. 2021 Jun 28;31(6):890-901. doi: 10.4014/jmb.2104.04002. [PubMed:34024892 ]
Radloff J, Pagitz M, Andrukhova O, Oberbauer R, Burgener IA, Erben RG: Aldosterone Is Positively Associated With Circulating FGF23 Levels in Chronic Kidney Disease Across Four Species, and May Drive FGF23 Secretion Directly. Front Physiol. 2021 Apr 29;12:649921. doi: 10.3389/fphys.2021.649921. eCollection 2021. [PubMed:33995120 ]
Pecori A, Buffolo F, Burrello J, Mengozzi G, Rumbolo F, Avataneo V, D'Avolio A, Rabbia F, Bertello C, Veglio F, Mulatero P, Monticone S: Mineralocorticoid Receptor Antagonist Effect on Aldosterone to Renin Ratio in Patients With Primary Aldosteronism. J Clin Endocrinol Metab. 2021 Aug 18;106(9):e3655-e3664. doi: 10.1210/clinem/dgab290. [PubMed:33942084 ]
Wagmann L, Vollmer AC, Lauder L, Mahfoud F, Meyer MR: Assessing Adherence to Antihypertensive Medication by Means of Dose-Dependent Reference Plasma Concentration Ranges and Ultra-High Performance Liquid Chromatography-Ion Trap Mass Spectrometry Analysis. Molecules. 2021 Mar 9;26(5). pii: molecules26051495. doi: 10.3390/molecules26051495. [PubMed:33803489 ]

Showing NP-Card for Canrenone (NP0000985)

MOL for NP0000985 (Canrenone)

3D MOL for NP0000985 (Canrenone)

3D SDF for NP0000985 (Canrenone)

3D-SDF for NP0000985 (Canrenone)

PDB for NP0000985 (Canrenone)

3D PDB for NP0000985 (Canrenone)

SMILES for NP0000985 (Canrenone)

INCHI for NP0000985 (Canrenone)

Structure for NP0000985 (Canrenone)

3D Structure for NP0000985 (Canrenone)