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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015467

Secondary Accession Numbers

HMDB15467

Metabolite Identification

Common Name

Drospirenone

Description

Drospirenone is a synthetic progestin that is an analog to spironolactone. It is found in a number of birth control formulations. Drospirenone differs from other synthetic progestins in that its pharmacological profile in preclinical studies shows it to be closer to the natural progesterone. As such it has anti-mineralocorticoid properties, counteracts the estrogen-stimulated activity of the renin-angiotensin-aldosterone system, and is not androgenic.

Structure

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

1395
  Mrv0541 02231215282D          

 34 40  0  0  1  0            999 V2000
    3.3963   -1.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170   -3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514    0.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3593    0.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1146   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3963   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6940    0.6641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7553   -1.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5842   -0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    1.4751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5023    0.4988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    2.1225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2005   -0.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    1.1330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7573   -0.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167    1.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593   -2.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270    0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -2.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    2.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590    1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2824    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    0.6194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932    0.6727    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -1.1817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107    1.1415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108    1.2677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1216    0.3647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0994    2.7439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 24  1  0  0  0  0
  2 24  2  0  0  0  0
  3 27  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 28  1  6  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 29  1  6  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 20  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  8 31  1  1  0  0  0
  9 18  1  0  0  0  0
 11 13  1  0  0  0  0
 11 15  1  0  0  0  0
 11 32  1  6  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 33  1  6  0  0  0
 13 15  1  0  0  0  0
 13 19  1  0  0  0  0
 13 34  1  6  0  0  0
 14 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 23  1  1  0  0  0
 18 22  1  0  0  0  0
 19 25  2  0  0  0  0
 21 26  1  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0015467
     RDKit          3D
Drospirenone
 57 63  0  0  0  0  0  0  0  0999 V2000
    1.7614    1.0982    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.1444   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3451    0.8253   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    1.2377   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885    0.1448   -0.6627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4638   -0.7357    0.4240 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9511   -1.0797    0.0816 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6439   -2.0452    0.9442 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5697   -1.7475    2.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -1.7677    0.6509 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1690   -0.5004   -0.1791 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5812   -0.8742   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652    0.3565   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211    1.0958   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    2.2114   -0.7917 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.3566    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -2.0209    0.3945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2230   -2.3375    1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -1.8092    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1693   -0.4199    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -0.1893    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.1965    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801    1.5290    1.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005    2.2091   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9108    1.7170   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817    0.7638   -0.1144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0644    1.4206    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4866    2.1374    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535    0.8641    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    1.2388    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.7797   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    0.1795   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    2.1737   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4555    1.5800   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -0.4688   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -0.3040    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -1.5278   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -3.1130    0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -2.6380    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -0.8355    2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139   -2.6194    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.2750   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983   -1.6483   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    0.9057   -2.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.0840   -2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -2.8923   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -1.7051    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -3.4158    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196   -2.5129   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -1.0185    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355    2.4791   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1129    3.1316    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    2.5689   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.2286   -2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    0.7216    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580    1.8683    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881    2.2539    1.3767 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  7  2  1  0
 10  8  1  0
 11 16  1  1
 19 17  1  0
 26 20  1  0
 11  2  1  0
 26  5  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  1
  7 37  1  6
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  1
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 21 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

1395
  Mrv0541 02231215282D          

 34 40  0  0  1  0            999 V2000
    3.3963   -1.6419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6170   -3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101    3.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514    0.0426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3593    0.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1146   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3963   -0.7108    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6940    0.6641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7553   -1.1763    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5842   -0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    1.4751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5023    0.4988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    2.1225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2005   -0.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1312    2.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    1.1330    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7573   -0.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146   -1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167    1.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8838   -1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593   -2.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270    0.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -2.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4054    2.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5590    1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2824    2.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    0.6194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2932    0.6727    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6906   -1.1817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1107    1.1415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8108    1.2677    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1216    0.3647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0994    2.7439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  1  0  0  0
  1 24  1  0  0  0  0
  2 24  2  0  0  0  0
  3 27  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 28  1  6  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 29  1  6  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 30  1  6  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
  7 20  1  1  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  8 31  1  1  0  0  0
  9 18  1  0  0  0  0
 11 13  1  0  0  0  0
 11 15  1  0  0  0  0
 11 32  1  6  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 33  1  6  0  0  0
 13 15  1  0  0  0  0
 13 19  1  0  0  0  0
 13 34  1  6  0  0  0
 14 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 21  1  0  0  0  0
 16 23  1  1  0  0  0
 18 22  1  0  0  0  0
 19 25  2  0  0  0  0
 21 26  1  0  0  0  0
 22 24  1  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015467

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

> <INCHI_KEY>
METQSPRSQINEEU-HXCATZOESA-N

> <FORMULA>
C24H30O3

> <MOLECULAR_WEIGHT>
366.4932

> <EXACT_MASS>
366.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
41.80862815363165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
3.3667613656666666

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.952565524845618

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
101.67719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yasmin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015467
     RDKit          3D
Drospirenone
 57 63  0  0  0  0  0  0  0  0999 V2000
    1.7614    1.0982    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.1444   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3451    0.8253   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    1.2377   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885    0.1448   -0.6627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4638   -0.7357    0.4240 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9511   -1.0797    0.0816 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6439   -2.0452    0.9442 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5697   -1.7475    2.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -1.7677    0.6509 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1690   -0.5004   -0.1791 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5812   -0.8742   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652    0.3565   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211    1.0958   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    2.2114   -0.7917 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.3566    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -2.0209    0.3945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2230   -2.3375    1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -1.8092    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1693   -0.4199    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -0.1893    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.1965    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801    1.5290    1.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005    2.2091   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9108    1.7170   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817    0.7638   -0.1144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0644    1.4206    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4866    2.1374    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535    0.8641    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    1.2388    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.7797   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    0.1795   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    2.1737   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4555    1.5800   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -0.4688   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -0.3040    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -1.5278   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -3.1130    0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -2.6380    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -0.8355    2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139   -2.6194    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.2750   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983   -1.6483   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    0.9057   -2.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.0840   -2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -2.8923   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -1.7051    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -3.4158    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196   -2.5129   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -1.0185    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355    2.4791   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1129    3.1316    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    2.5689   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.2286   -2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    0.7216    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580    1.8683    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881    2.2539    1.3767 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  7  2  1  0
 10  8  1  0
 11 16  1  1
 19 17  1  0
 26 20  1  0
 11  2  1  0
 26  5  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  1
  7 37  1  6
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  1
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 21 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1395                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.340  -3.065   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.752  -5.667   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.712   5.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.883   0.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.404   0.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.947  -1.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.340  -1.327   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.896   1.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.143  -2.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.957  -0.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.364   2.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.404   0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.419   3.962   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.841  -1.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.845   4.272   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.487   2.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.880  -0.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.947  -3.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.991   3.641   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.250  -2.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.116   1.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.404  -4.471   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.944   0.709   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.883  -4.471   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.090   4.900   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.244   2.975   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.727   4.565   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       5.393   1.156   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.281   1.256   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.156  -2.206   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.673   2.131   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.247   2.366   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       9.560   0.681   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.652   5.122   0.000  0.00  0.00           H+0
CONECT    1    9   24                                                       
CONECT    2   24                                                            
CONECT    3   27                                                            
CONECT    4    5    7    8   28                                             
CONECT    5    4    6   10   29                                             
CONECT    6    5    9   10   30                                             
CONECT    7    4    9   14   20                                             
CONECT    8    4   11   12   31                                             
CONECT    9    1    6    7   18                                             
CONECT   10    5    6                                                       
CONECT   11    8   13   15   32                                             
CONECT   12    8   16   17   33                                             
CONECT   13   11   15   19   34                                             
CONECT   14    7   17                                                       
CONECT   15   11   13                                                       
CONECT   16   12   19   21   23                                             
CONECT   17   12   14                                                       
CONECT   18    9   22                                                       
CONECT   19   13   16   25                                                  
CONECT   20    7                                                            
CONECT   21   16   26                                                       
CONECT   22   18   24                                                       
CONECT   23   16                                                            
CONECT   24    1    2   22                                                  
CONECT   25   19   27                                                       
CONECT   26   21   27                                                       
CONECT   27    3   25   26                                                  
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    8                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

COMPND    HMDB0015467
HETATM    1  C1  UNL     1       1.761   1.098   1.066  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.831   0.144  -0.065  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.345   0.825  -1.312  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.096   1.238  -1.101  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.988   0.145  -0.663  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.464  -0.736   0.424  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.951  -1.080   0.082  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.644  -2.045   0.944  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.570  -1.747   2.026  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.118  -1.768   0.651  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.169  -0.500  -0.179  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.581  -0.874  -1.561  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.265   0.356  -2.116  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.621   1.096  -0.900  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.185   2.211  -0.792  1.00  0.00           O  
HETATM   16  O2  UNL     1       4.228   0.357   0.231  1.00  0.00           O  
HETATM   17  C15 UNL     1      -1.260  -2.021   0.395  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.223  -2.337   1.473  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.685  -1.809   0.141  1.00  0.00           C  
HETATM   20  C18 UNL     1      -3.169  -0.420   0.130  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.459  -0.189   0.347  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.905   1.196   0.329  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.880   1.529   1.015  1.00  0.00           O  
HETATM   24  C21 UNL     1      -4.201   2.209  -0.502  1.00  0.00           C  
HETATM   25  C22 UNL     1      -2.911   1.717  -1.073  1.00  0.00           C  
HETATM   26  C23 UNL     1      -2.282   0.764  -0.114  1.00  0.00           C  
HETATM   27  C24 UNL     1      -2.064   1.421   1.219  1.00  0.00           C  
HETATM   28  H1  UNL     1       1.487   2.137   0.713  1.00  0.00           H  
HETATM   29  H2  UNL     1       1.053   0.864   1.860  1.00  0.00           H  
HETATM   30  H3  UNL     1       2.811   1.239   1.463  1.00  0.00           H  
HETATM   31  H4  UNL     1       1.915   1.780  -1.463  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.370   0.180  -2.195  1.00  0.00           H  
HETATM   33  H6  UNL     1      -0.171   2.174  -0.474  1.00  0.00           H  
HETATM   34  H7  UNL     1      -0.456   1.580  -2.118  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.309  -0.469  -1.539  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.562  -0.304   1.440  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.911  -1.528  -0.959  1.00  0.00           H  
HETATM   38  H11 UNL     1       1.300  -3.113   0.801  1.00  0.00           H  
HETATM   39  H12 UNL     1       2.884  -2.638   2.649  1.00  0.00           H  
HETATM   40  H13 UNL     1       2.549  -0.835   2.638  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.714  -2.619   0.299  1.00  0.00           H  
HETATM   42  H15 UNL     1       2.798  -1.275  -2.200  1.00  0.00           H  
HETATM   43  H16 UNL     1       4.398  -1.648  -1.459  1.00  0.00           H  
HETATM   44  H17 UNL     1       3.671   0.906  -2.844  1.00  0.00           H  
HETATM   45  H18 UNL     1       5.228   0.084  -2.640  1.00  0.00           H  
HETATM   46  H19 UNL     1      -0.801  -2.892  -0.160  1.00  0.00           H  
HETATM   47  H20 UNL     1      -2.292  -1.705   2.369  1.00  0.00           H  
HETATM   48  H21 UNL     1      -2.377  -3.416   1.683  1.00  0.00           H  
HETATM   49  H22 UNL     1      -3.220  -2.513  -0.553  1.00  0.00           H  
HETATM   50  H23 UNL     1      -5.149  -1.019   0.531  1.00  0.00           H  
HETATM   51  H24 UNL     1      -4.936   2.479  -1.318  1.00  0.00           H  
HETATM   52  H25 UNL     1      -4.113   3.132   0.104  1.00  0.00           H  
HETATM   53  H26 UNL     1      -2.254   2.569  -1.246  1.00  0.00           H  
HETATM   54  H27 UNL     1      -3.086   1.229  -2.052  1.00  0.00           H  
HETATM   55  H28 UNL     1      -2.201   0.722   2.080  1.00  0.00           H  
HETATM   56  H29 UNL     1      -1.058   1.868   1.337  1.00  0.00           H  
HETATM   57  H30 UNL     1      -2.788   2.254   1.377  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    7   11
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6   26   35
CONECT    6    7   17   36
CONECT    7    8   37
CONECT    8    9   10   38
CONECT    9   10   39   40
CONECT   10   11   41
CONECT   11   12   16
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   15   16
CONECT   17   18   19   46
CONECT   18   19   47   48
CONECT   19   20   49
CONECT   20   21   21   26
CONECT   21   22   50
CONECT   22   23   23   24
CONECT   24   25   51   52
CONECT   25   26   53   54
CONECT   26   27
CONECT   27   55   56   57
END

HMDB0015467
     RDKit          3D
Drospirenone
 57 63  0  0  0  0  0  0  0  0999 V2000
    1.7614    1.0982    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312    0.1444   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3451    0.8253   -1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    1.2377   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9885    0.1448   -0.6627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4638   -0.7357    0.4240 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9511   -1.0797    0.0816 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6439   -2.0452    0.9442 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5697   -1.7475    2.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175   -1.7677    0.6509 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1690   -0.5004   -0.1791 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5812   -0.8742   -1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652    0.3565   -2.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6211    1.0958   -0.9003 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    2.2114   -0.7917 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.3566    0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -2.0209    0.3945 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2230   -2.3375    1.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854   -1.8092    0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1693   -0.4199    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4587   -0.1893    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    1.1965    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8801    1.5290    1.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005    2.2091   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9108    1.7170   -1.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2817    0.7638   -0.1144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0644    1.4206    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4866    2.1374    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0535    0.8641    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    1.2388    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.7797   -1.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700    0.1795   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    2.1737   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4555    1.5800   -2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3094   -0.4688   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -0.3040    1.4402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -1.5278   -0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3002   -3.1130    0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -2.6380    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -0.8355    2.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139   -2.6194    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -1.2750   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3983   -1.6483   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715    0.9057   -2.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278    0.0840   -2.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -2.8923   -0.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -1.7051    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -3.4158    1.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196   -2.5129   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1487   -1.0185    0.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9355    2.4791   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1129    3.1316    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    2.5689   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.2286   -2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    0.7216    2.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0580    1.8683    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881    2.2539    1.3767 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  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  7  2  1  0
 10  8  1  0
 11 16  1  1
 19 17  1  0
 26 20  1  0
 11  2  1  0
 26  5  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  1
  7 37  1  6
  8 38  1  1
  9 39  1  0
  9 40  1  0
 10 41  1  1
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 19 49  1  6
 21 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydrospirorenone	ChEBI
6beta,7Beta;15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone	ChEBI
Dehydrospirorenone	ChEBI
Drospirenona	ChEBI
Drospirenonum	ChEBI
Slynd	Kegg
6b,7Beta;15b,16b-dimethylene-3-oxo-17a-pregn-4-ene-21,17-carbolactone	Generator
6Β,7beta;15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone	Generator
6Β,7β,15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17 carbolactone	HMDB
DRSP	HMDB
1,2-Dihydro-spirorenone	HMDB
Dihydrospirorenone	HMDB
6beta,7beta,15beta,16beta-Dimethylen-3-oxo-17alpha-pregn-4-en-21,17-carbolacton	HMDB

Chemical Formula

C₂₄H₃₀O₃

Average Molecular Weight

366.4932

Monoisotopic Molecular Weight

366.219494826

IUPAC Name

(1R,2R,4R,10R,11S,14S,15S,16S,18S,19S)-10,14-dimethylspiro[hexacyclo[9.8.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁹.0¹⁶,¹⁸]nonadecane-15,2'-oxolan]-5-ene-5',7-dione

Traditional Name

yasmin

CAS Registry Number

67392-87-4

SMILES

[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21

InChI Identifier

InChI=1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1

InChI Key

METQSPRSQINEEU-HXCATZOESA-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
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:50838 )
3-oxo Delta(4)-steroid (CHEBI:50838 )
steroid lactone (CHEBI:50838 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015467)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0022 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	2.36	ALOGPS
logP	3.37	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-5	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	101.68 m³·mol⁻¹	ChemAxon
Polarizability	41.81 Å³	ChemAxon
Number of Rings	7	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]+	187.053	31661259
DarkChem	[M-H]-	182.917	31661259
DeepCCS	[M-2H]-	222.146	30932474
DeepCCS	[M+Na]+	196.163	30932474
AllCCS	[M+H]+	191.0	32859911
AllCCS	[M+H-H2O]+	188.6	32859911
AllCCS	[M+NH4]+	193.3	32859911
AllCCS	[M+Na]+	193.9	32859911
AllCCS	[M-H]-	197.9	32859911
AllCCS	[M+Na-2H]-	198.0	32859911
AllCCS	[M+HCOO]-	198.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Drospirenone	[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21	3984.7	Standard polar	33892256
Drospirenone	[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21	3100.1	Standard non polar	33892256
Drospirenone	[H][C@@]12C[C@]1([H])[C@@]1([H])[C@]3([H])[C@]4([H])C[C@]4([H])[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@]1([H])[C@@]1(C)CCC(=O)C=C21	3604.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Drospirenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C	3167.8	Semi standard non polar	33892256
Drospirenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C	3136.1	Standard non polar	33892256
Drospirenone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@H]([C@@H]1[C@@H]1C[C@@H]1[C@@]21CCC(=O)O1)[C@H]1C[C@H]1C1=CC(O[Si](C)(C)C)=CC[C@@]13C	3626.8	Standard polar	33892256
Drospirenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3419.3	Semi standard non polar	33892256
Drospirenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3380.5	Standard non polar	33892256
Drospirenone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)[C@@H]1C[C@@H]1[C@H]1[C@@H]3[C@@H]4C[C@@H]4[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]12	3761.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Drospirenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w9c-0169000000-37155c35a2dfebdf3836	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Drospirenone 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 - Drospirenone 50V, Positive-QTOF	splash10-055f-0900000000-772901ee1c9dba98a43f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOF	splash10-014i-0009000000-300e8223fa42b1134cab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOF	splash10-014i-0009000000-53df13fe7fdac4782410	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 30V, Positive-QTOF	splash10-00r2-0941000000-98ac83e1ebad8a375bf2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 50V, Positive-QTOF	splash10-055f-0900000000-da66174427c7e2f2c7ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOF	splash10-0532-0910000000-364eccbcf5d287156d5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOF	splash10-0532-0910000000-da3aa3811e9eaf4b9c18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Drospirenone 30V, Positive-QTOF	splash10-00r2-0941000000-7a161e31078b8238f558	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOF	splash10-014i-0019000000-1287f5a96f64146a88cf	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOF	splash10-066v-0059000000-42514644851cc67da776	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOF	splash10-0cdi-2490000000-ad1a0e6e02a199b65609	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 10V, Negative-QTOF	splash10-014i-0009000000-a9189466642bfd0f55d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 20V, Negative-QTOF	splash10-01b9-0009000000-bf5682f6dc8a5a63079b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 40V, Negative-QTOF	splash10-00kf-7059000000-fc557f2b38e64b366f1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 10V, Positive-QTOF	splash10-014i-0009000000-fdfa94d563b812aaf622	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 20V, Positive-QTOF	splash10-014i-0329000000-e846c7e35c919773fa04	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 40V, Positive-QTOF	splash10-000l-0942000000-43df2f2243fbd4d876e6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 10V, Negative-QTOF	splash10-014i-0009000000-174ae70c06846ef08cd2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 20V, Negative-QTOF	splash10-014i-0009000000-bfcf28dede045890094d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Drospirenone 40V, Negative-QTOF	splash10-0296-1039000000-7d134b564b09ff7dfdb9	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01395	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01395	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01395

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Drospirenone

METLIN ID

Not Available

PubChem Compound

68873

PDB ID

Not Available

ChEBI ID

50838

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

Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
Wichianpitaya J, Taneepanichskul S: A comparative efficacy of low-dose combined oral contraceptives containing desogestrel and drospirenone in premenstrual symptoms. Obstet Gynecol Int. 2013;2013:487143. doi: 10.1155/2013/487143. Epub 2013 Feb 20. [PubMed:23577032 ]
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. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Koitka M, Hochel J, Gieschen H, Borchert HH: Improving the ex vivo stability of drug ester compounds in rat and dog serum: inhibition of the specific esterases and implications on their identity. J Pharm Biomed Anal. 2010 Feb 5;51(3):664-78. doi: 10.1016/j.jpba.2009.09.023. Epub 2009 Sep 23. [PubMed:19850433 ]

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Maia H Jr, Casoy J, Athayde C, Valente Filho J, Coutinho EM: The effect of a continuous regimen of drospirenone 3 mg/ethinylestradiol 30 microg on Cox-2 and Ki-67 expression in the endometrium. Eur J Contracept Reprod Health Care. 2010 Feb;15(1):35-40. doi: 10.3109/13625180903383928. [PubMed:20063991 ]

Enzyme Details

3. Androgen receptor

General function:: Involved in DNA binding
Specific function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:: AR
Uniprot ID:: P10275
Molecular weight:: 98987.9

References

Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]

Enzyme Details

4. Progesterone receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:: PGR
Uniprot ID:: P06401
Molecular weight:: 98980.0

References

Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
Bray JD, Jelinsky S, Ghatge R, Bray JA, Tunkey C, Saraf K, Jacobsen BM, Richer JK, Brown EL, Winneker RC, Horwitz KB, Lyttle CR: Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. J Steroid Biochem Mol Biol. 2005 Dec;97(4):328-41. Epub 2005 Sep 12. [PubMed:16157482 ]
Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [PubMed:8922878 ]
Arias-Loza PA, Hu K, Schafer A, Bauersachs J, Quaschning T, Galle J, Jazbutyte V, Neyses L, Ertl G, Fritzemeier KH, Hegele-Hartung C, Pelzer T: Medroxyprogesterone acetate but not drospirenone ablates the protective function of 17 beta-estradiol in aldosterone salt-treated rats. Hypertension. 2006 Nov;48(5):994-1001. Epub 2006 Sep 25. [PubMed:17000933 ]
Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. [PubMed:16291771 ]
Sitruk-Ware R: New progestogens: a review of their effects in perimenopausal and postmenopausal women. Drugs Aging. 2004;21(13):865-83. [PubMed:15493951 ]

Enzyme Details

5. 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

Krattenmacher R: Drospirenone: pharmacology and pharmacokinetics of a unique progestogen. Contraception. 2000 Jul;62(1):29-38. [PubMed:11024226 ]
Fuhrmann U, Krattenmacher R, Slater EP, Fritzemeier KH: The novel progestin drospirenone and its natural counterpart progesterone: biochemical profile and antiandrogenic potential. Contraception. 1996 Oct;54(4):243-51. [PubMed:8922878 ]
Muhn P, Fuhrmann U, Fritzemeier KH, Krattenmacher R, Schillinger E: Drospirenone: a novel progestogen with antimineralocorticoid and antiandrogenic activity. Ann N Y Acad Sci. 1995 Jun 12;761:311-35. [PubMed:7625729 ]
Oelkers WK: Effects of estrogens and progestogens on the renin-aldosterone system and blood pressure. Steroids. 1996 Apr;61(4):166-71. [PubMed:8732994 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Drospirenone (HMDB0015467)

MOL for HMDB0015467 (Drospirenone)

3D MOL for HMDB0015467 (Drospirenone)

3D SDF for HMDB0015467 (Drospirenone)

3D-SDF for HMDB0015467 (Drospirenone)

PDB for HMDB0015467 (Drospirenone)

3D PDB for HMDB0015467 (Drospirenone)

SMILES for HMDB0015467 (Drospirenone)

INCHI for HMDB0015467 (Drospirenone)

Structure for HMDB0015467 (Drospirenone)

3D Structure for HMDB0015467 (Drospirenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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