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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2008-08-06 13:21:05 UTC

Update Date

2021-09-14 15:40:02 UTC

HMDB ID

HMDB0006756

Secondary Accession Numbers

HMDB06756

Metabolite Identification

Common Name

21-Hydroxy-5b-pregnane-3,11,20-trione

Description

21-Hydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 21-Hydroxy-5beta-pregnane-3,11,20-trione is the. second to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from 11-Dehydrocorticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).

Structure

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


  Mrv0541 02231220502D          

 29 32  0  0  1  0            999 V2000
   16.3708   -8.6675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9096   -8.8464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1641  -10.2876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3172   -7.7033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9668   -7.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0445   -6.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9833   -9.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6276   -9.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9619   -8.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3410   -7.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6782   -8.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3225   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5706   -9.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2554   -6.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6672   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2149   -9.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8022   -9.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5035   -8.4225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1479   -7.9073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7612   -6.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6111   -7.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8952   -5.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7351   -8.1222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0908   -8.6374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0238   -7.0917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3052   -6.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1578  -10.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8427   -7.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2573   -5.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 24  5  1  1  0  0  0
 25  6  1  1  0  0  0
  7 16  1  0  0  0  0
  7  8  1  0  0  0  0
 18  8  1  0  0  0  0
  9 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 24  1  0  0  0  0
 13 17  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 26  1  0  0  0  0
 16 24  1  0  0  0  0
 17 27  2  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 25  1  0  0  0  0
 20 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 28  2  0  0  0  0
 23 21  1  0  0  0  0
 22 29  2  0  0  0  0
 23 24  1  0  0  0  0
 18  4  1  1  0  0  0
 16  3  1  1  0  0  0
 23  2  1  6  0  0  0
 19  1  1  6  0  0  0
M  END

HMDB0006756
     RDKit          3D
21-Hydroxy-5b-pregnane-3,11,20-trione
 55 58  0  0  0  0  0  0  0  0999 V2000
    1.7131    1.5618   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702    0.2033   -0.4558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5171   -0.8413   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -0.6317   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -0.4564   -2.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188   -0.6619   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2613    0.4443    0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2087    0.7078    1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423    1.3657    0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.8337   -0.4135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2760    0.9026   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084   -0.0658    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0987    0.0310    0.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523   -1.1472    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9581   -1.6105    0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -0.5747   -0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9041   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0879    0.0158    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    0.7530    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.0889    1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.1140    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2431   -0.8827   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -1.6280   -1.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438   -1.0718    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9677   -0.1845    1.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.3569   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    1.5168   -1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    1.8398   -1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.7653   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8406   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492   -1.6132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    1.3505   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    1.4679    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -0.1372    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    1.3910    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    2.4497    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    1.4587   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.7726   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5465    1.9562   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -0.9037    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571   -2.0241    1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303   -2.5264   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307   -2.0297    0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.0291   -2.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1590   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -1.8181   -2.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295   -1.0692    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    1.8287    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552    0.5563    2.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916   -0.9407    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126    0.6490    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    1.1207   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8184   -2.1095    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3474   -0.9031   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007    0.1272    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END


  Mrv0541 02231220502D          

 29 32  0  0  1  0            999 V2000
   16.3708   -8.6675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9096   -8.8464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1641  -10.2876    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3172   -7.7033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9668   -7.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0445   -6.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9833   -9.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6276   -9.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9619   -8.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3410   -7.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6782   -8.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3225   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5706   -9.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2554   -6.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6672   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2149   -9.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8022   -9.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5035   -8.4225    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1479   -7.9073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.7612   -6.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6111   -7.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8952   -5.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7351   -8.1222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.0908   -8.6374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.0238   -7.0917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.3052   -6.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1578  -10.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8427   -7.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2573   -5.3845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 24  5  1  1  0  0  0
 25  6  1  1  0  0  0
  7 16  1  0  0  0  0
  7  8  1  0  0  0  0
 18  8  1  0  0  0  0
  9 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 24  1  0  0  0  0
 13 17  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 26  1  0  0  0  0
 16 24  1  0  0  0  0
 17 27  2  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 25  1  0  0  0  0
 20 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 28  2  0  0  0  0
 23 21  1  0  0  0  0
 22 29  2  0  0  0  0
 23 24  1  0  0  0  0
 18  4  1  1  0  0  0
 16  3  1  1  0  0  0
 23  2  1  6  0  0  0
 19  1  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006756

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1

> <INCHI_KEY>
ZDUVZJUTJOBJHS-HNEBDTNWSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.4605

> <EXACT_MASS>
346.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.672908490563486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.453940146333333

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.450287420227777

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.864708551397047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2953240661923715

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
94.24809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006756
     RDKit          3D
21-Hydroxy-5b-pregnane-3,11,20-trione
 55 58  0  0  0  0  0  0  0  0999 V2000
    1.7131    1.5618   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702    0.2033   -0.4558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5171   -0.8413   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -0.6317   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -0.4564   -2.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188   -0.6619   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2613    0.4443    0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2087    0.7078    1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423    1.3657    0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.8337   -0.4135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2760    0.9026   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084   -0.0658    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0987    0.0310    0.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523   -1.1472    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9581   -1.6105    0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -0.5747   -0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9041   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0879    0.0158    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    0.7530    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.0889    1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.1140    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2431   -0.8827   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -1.6280   -1.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438   -1.0718    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9677   -0.1845    1.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.3569   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    1.5168   -1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    1.8398   -1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.7653   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8406   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492   -1.6132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    1.3505   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    1.4679    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -0.1372    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    1.3910    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    2.4497    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    1.4587   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.7726   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5465    1.9562   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -0.9037    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571   -2.0241    1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303   -2.5264   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307   -2.0297    0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.0291   -2.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1590   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -1.8181   -2.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295   -1.0692    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    1.8287    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552    0.5563    2.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916   -0.9407    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126    0.6490    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    1.1207   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8184   -2.1095    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3474   -0.9031   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007    0.1272    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  H   UNK     0      30.559 -16.179   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      27.831 -16.513   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      26.440 -19.204   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0      28.592 -14.379   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      26.071 -14.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.950 -11.698   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.969 -18.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.172 -17.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.662 -15.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.370 -13.643   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.666 -16.524   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.869 -15.562   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.332 -18.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.477 -12.677   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.979 -10.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.534 -17.646   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.897 -18.047   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.940 -15.722   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.143 -14.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.288 -12.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.274 -13.639   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.538 -11.028   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      27.506 -15.161   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.303 -16.123   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.911 -13.238   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      34.170 -11.461   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      22.695 -19.008   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      25.840 -13.078   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      30.347 -10.051   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   23                                                            
CONECT    3   16                                                            
CONECT    4   18                                                            
CONECT    5   24                                                            
CONECT    6   25                                                            
CONECT    7   16    8                                                       
CONECT    8    7   18                                                       
CONECT    9   19   10                                                       
CONECT   10    9   20                                                       
CONECT   11   12   17                                                       
CONECT   12   11   24                                                       
CONECT   13   17   16                                                       
CONECT   14   25   21                                                       
CONECT   15   22   26                                                       
CONECT   16    7   13   24    3                                             
CONECT   17   11   13   27                                                  
CONECT   18    8   19   23    4                                             
CONECT   19    9   18   25    1                                             
CONECT   20   10   22   25                                                  
CONECT   21   14   28   23                                                  
CONECT   22   15   20   29                                                  
CONECT   23   18   21   24    2                                             
CONECT   24    5   12   16   23                                             
CONECT   25    6   14   19   20                                             
CONECT   26   15                                                            
CONECT   27   17                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0006756
HETATM    1  C1  UNL     1       1.713   1.562  -1.078  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.970   0.203  -0.456  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.517  -0.841  -1.421  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.034  -0.632  -1.655  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.336  -0.456  -2.792  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.819  -0.662  -0.468  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.261   0.444   0.446  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.209   0.708   1.559  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.442   1.366   0.938  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.754   0.834  -0.414  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.276   0.903  -0.599  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.908  -0.066   0.305  1.00  0.00           C  
HETATM   13  O2  UNL     1      -6.099   0.031   0.532  1.00  0.00           O  
HETATM   14  C12 UNL     1      -4.152  -1.147   0.945  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.958  -1.611   0.196  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.277  -0.575  -0.660  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.669  -0.904  -2.102  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.088   0.016   0.791  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.837   0.753   1.819  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.216   0.089   1.626  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.324   0.114   0.095  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.243  -0.883  -0.422  1.00  0.00           C  
HETATM   23  O3  UNL     1       3.897  -1.628  -1.307  1.00  0.00           O  
HETATM   24  C21 UNL     1       5.644  -1.072   0.071  1.00  0.00           C  
HETATM   25  O4  UNL     1       5.968  -0.185   1.083  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.524   2.357  -0.360  1.00  0.00           H  
HETATM   27  H2  UNL     1       0.936   1.517  -1.853  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.662   1.840  -1.625  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.061  -0.765  -2.361  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.649  -1.841  -0.953  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.549  -1.613   0.083  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.237   1.350  -0.197  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.721   1.468   2.237  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.456  -0.137   2.198  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.294   1.391   1.640  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.149   2.450   0.803  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.336   1.459  -1.231  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.554   0.773  -1.651  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.547   1.956  -0.319  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.881  -0.904   2.016  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.857  -2.024   1.059  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.230  -2.526  -0.410  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.231  -2.030   0.954  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.622  -0.029  -2.762  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.772  -1.159  -2.058  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.194  -1.818  -2.472  1.00  0.00           H  
HETATM   47  H22 UNL     1       1.129  -1.069   1.016  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.917   1.829   1.685  1.00  0.00           H  
HETATM   49  H24 UNL     1       1.455   0.556   2.836  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.092  -0.941   2.009  1.00  0.00           H  
HETATM   51  H26 UNL     1       4.013   0.649   2.113  1.00  0.00           H  
HETATM   52  H27 UNL     1       3.834   1.121  -0.088  1.00  0.00           H  
HETATM   53  H28 UNL     1       5.818  -2.110   0.417  1.00  0.00           H  
HETATM   54  H29 UNL     1       6.347  -0.903  -0.771  1.00  0.00           H  
HETATM   55  H30 UNL     1       6.901   0.127   1.011  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   18   21
CONECT    3    4   29   30
CONECT    4    5    5    6
CONECT    6    7   16   31
CONECT    7    8   18   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   16   37
CONECT   11   12   38   39
CONECT   12   13   13   14
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17
CONECT   17   44   45   46
CONECT   18   19   47
CONECT   19   20   48   49
CONECT   20   21   50   51
CONECT   21   22   52
CONECT   22   23   23   24
CONECT   24   25   53   54
CONECT   25   55
END

HMDB0006756
     RDKit          3D
21-Hydroxy-5b-pregnane-3,11,20-trione
 55 58  0  0  0  0  0  0  0  0999 V2000
    1.7131    1.5618   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9702    0.2033   -0.4558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5171   -0.8413   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -0.6317   -1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360   -0.4564   -2.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188   -0.6619   -0.4681 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2613    0.4443    0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2087    0.7078    1.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4423    1.3657    0.9377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    0.8337   -0.4135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2760    0.9026   -0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084   -0.0658    0.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0987    0.0310    0.5322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1523   -1.1472    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9581   -1.6105    0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2773   -0.5747   -0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6686   -0.9041   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0879    0.0158    0.7908 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8374    0.7530    1.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.0889    1.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.1140    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2431   -0.8827   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -1.6280   -1.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6438   -1.0718    0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9677   -0.1845    1.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245    2.3569   -0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359    1.5168   -1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    1.8398   -1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.7653   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6488   -1.8406   -0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5492   -1.6132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    1.3505   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    1.4679    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556   -0.1372    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2938    1.3910    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1495    2.4497    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    1.4587   -1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5536    0.7726   -1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5465    1.9562   -0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -0.9037    2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571   -2.0241    1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303   -2.5264   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307   -2.0297    0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -0.0291   -2.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7716   -1.1590   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936   -1.8181   -2.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295   -1.0692    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    1.8287    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4552    0.5563    2.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0916   -0.9407    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126    0.6490    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    1.1207   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8184   -2.1095    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3474   -0.9031   -0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007    0.1272    1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  6
 11 38  1  0
 11 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3alpha-Hydroxy-5beta-pregnane-20-one	HMDB
21-Hydroxy-5beta-pregnane-3,11,20-trione	HMDB

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

IUPAC Name

(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione

Traditional Name

(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione

CAS Registry Number

10417-86-4

SMILES

[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1

InChI Key

ZDUVZJUTJOBJHS-HNEBDTNWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location

Excreta

Feces

Cellular substructure

Extracellular

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	10^(2.63) g/L	ALOGPS
logP	10^(2.45) g/L	ChemAxon
logS	10^(-3.8) g/L	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.25 m³·mol⁻¹	ChemAxon
Polarizability	38.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.289	31661259
DarkChem	[M-H]-	181.352	31661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#1	C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=O)CO[Si](C)(C)C	3233.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#2	C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2=C(CO)O[Si](C)(C)C	3177.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#3	C[C@]12CC(O[Si](C)(C)C)=C3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=O)CO	3106.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#4	C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=CO)O[Si](C)(C)C	3206.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#5	C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@]2(C)C(C(=O)CO)CC[C@@H]12	3067.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#6	C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CCC2C(=O)CO	3217.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#7	C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2C(=O)CO	3219.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#1	CC(C)(C)[Si](C)(C)OCC(=O)C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C	3490.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#2	CC(C)(C)[Si](C)(C)OC(CO)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C	3435.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#3	CC(C)(C)[Si](C)(C)OC1=C2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@H]2CCC(C(=O)CO)[C@@]2(C)C1	3344.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#4	CC(C)(C)[Si](C)(C)OC(=CO)C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C	3430.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#5	CC(C)(C)[Si](C)(C)OC1=C[C@]2(C)C(C(=O)CO)CC[C@H]2[C@@H]2CC[C@@H]3CC(=O)CC[C@]3(C)[C@@H]12	3280.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#6	CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(=O)C[C@]4(C)C(C(=O)CO)CC[C@H]4[C@@H]3CC[C@@H]2C1	3464.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#7	CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CCC(C(=O)CO)[C@@]4(C)CC(=O)[C@@H]3[C@@]2(C)CC1	3454.8	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fki-1988000000-fba247baf630a7210351	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (1 TMS) - 70eV, Positive	splash10-0udr-2639300000-c9ca38b4ccbbd8f2986e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Positive-QTOF	splash10-002b-0019000000-24f7d25b96d058ce27ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Positive-QTOF	splash10-016r-0139000000-14964e5f329435527649	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Positive-QTOF	splash10-0a4s-3293000000-fdc80d45785ab54b814f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Negative-QTOF	splash10-0002-0009000000-804a5ed2772af86708b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Negative-QTOF	splash10-05p2-1029000000-b83f2a0acc0792e5262b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Negative-QTOF	splash10-0a4r-5092000000-c68952d24a29d9931c16	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Negative-QTOF	splash10-002b-0009000000-33bcf2e22dc5313c0e4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Negative-QTOF	splash10-03ys-0049000000-9e885d9932104c564774	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Negative-QTOF	splash10-006t-0193000000-d4a852e1dae01823cdfc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Positive-QTOF	splash10-002b-0009000000-962664f8be4e6a4a1d65	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Positive-QTOF	splash10-03fr-0269000000-d077f7e8c79f38b5e3ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Positive-QTOF	splash10-03di-4690000000-b76906ca897f4798e371	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	28701177	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Sepsis	28701177	details

Associated Disorders and Diseases

Disease References

Sepsis
Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024063

KNApSAcK ID

Not Available

Chemspider ID

23141070

KEGG Compound ID

C05480

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779614

PDB ID

Not Available

ChEBI ID

88767

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

Not Available

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Ion	details
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADP → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADPH + Hydrogen Ion	details

Enzyme Details

2. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Showing metabocard for 21-Hydroxy-5b-pregnane-3,11,20-trione (HMDB0006756)

MOL for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

3D MOL for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

3D SDF for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

3D-SDF for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

PDB for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

3D PDB for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

SMILES for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

INCHI for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

Structure for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

3D Structure for HMDB0006756 (21-Hydroxy-5b-pregnane-3,11,20-trione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions