Jump To Section:

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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 04:25:20 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003759

Secondary Accession Numbers

HMDB03759

Metabolite Identification

Common Name

5a-Pregnane-3,20-dione

Description

5a-Pregnane-3,20-dione, also known as 5alpha-dihydroprogesterone or 3,20-allopregnanedione, 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. Thus, 5a-pregnane-3,20-dione is considered to be a steroid. Based on a literature review a significant number of articles have been published on 5a-Pregnane-3,20-dione.

Structure

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

HMDB03759.mol
  Mrv0541 02231219472D          

 27 30  0  0  0  0            999 V2000
   -2.3522   -0.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -1.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.4302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9233   -0.6052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6377   -0.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.6052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -0.1927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2201   -0.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2201    0.6323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5057    1.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    0.8872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0667   -1.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597    1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.2198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -2.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.0177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    2.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.0177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 17 19  1  1  0  0  0
 12 20  1  1  0  0  0
  9 21  1  1  0  0  0
  5 22  1  1  0  0  0
  4 23  1  6  0  0  0
 10 24  1  6  0  0  0
 19 25  2  0  0  0  0
 19 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END

HMDB0003759
     RDKit          3D
5a-Pregnane-3,20-dione
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.8264   -0.5208   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.8967   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.9621   -0.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483    0.0566    0.4026 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5484    1.2995   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0331   -1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452    0.7713   -0.3661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0076    0.2690   -0.7056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6638    1.3210   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372    0.7158   -1.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    0.6731   -0.6644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2516    0.2511   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.3985    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.9814    0.3043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4062   -0.1743    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    0.1126    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1692    0.4238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2997   -1.6048    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790    0.3131    0.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0914   -0.2804    1.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -0.1747    1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.3380    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6730   -1.6981   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970    0.5378    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2064   -0.5533   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4735   -1.2337    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7816    0.3609    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040    2.1773    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807    1.3297   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.1846   -2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1236    1.9123   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.6760    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.7036   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    2.2448   -1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.4012   -2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883    1.2920   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -0.2786   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745    1.7103   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.7752   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6387    0.9235   -1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253   -1.2548    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9169    0.3305    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -0.6085    2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1298    2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -1.8069   -1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.8677    0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405   -2.3074    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    1.4247    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -1.3505    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    0.2409    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    0.7793    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971   -0.9877    2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2150   -2.4725    0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -1.9110    0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -1.9215   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HMDB03759.mol
  Mrv0541 02231219472D          

 27 30  0  0  0  0            999 V2000
   -2.3522   -0.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -1.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.4302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9233   -0.6052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6377   -0.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.6052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -0.1927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2201   -0.1927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2201    0.6323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5057    1.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    0.8872    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0667   -1.8427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2597    1.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.2198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049    0.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -2.2552    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.0177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    2.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.0177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 17 19  1  1  0  0  0
 12 20  1  1  0  0  0
  9 21  1  1  0  0  0
  5 22  1  1  0  0  0
  4 23  1  6  0  0  0
 10 24  1  6  0  0  0
 19 25  2  0  0  0  0
 19 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0003759

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
XMRPGKVKISIQBV-BJMCWZGWSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.861887083896086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.194438735666669

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.343395658319462

> <JCHEM_PKA_STRONGEST_BASIC>
-7.053949180108259

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
91.87859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5a-pregnane-3,20-dione

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0003759
     RDKit          3D
5a-Pregnane-3,20-dione
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.8264   -0.5208   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.8967   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.9621   -0.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483    0.0566    0.4026 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5484    1.2995   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0331   -1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452    0.7713   -0.3661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0076    0.2690   -0.7056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6638    1.3210   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372    0.7158   -1.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    0.6731   -0.6644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2516    0.2511   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.3985    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.9814    0.3043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4062   -0.1743    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    0.1126    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1692    0.4238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2997   -1.6048    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790    0.3131    0.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0914   -0.2804    1.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -0.1747    1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.3380    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6730   -1.6981   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970    0.5378    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2064   -0.5533   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4735   -1.2337    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7816    0.3609    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040    2.1773    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807    1.3297   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.1846   -2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1236    1.9123   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.6760    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.7036   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    2.2448   -1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.4012   -2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883    1.2920   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -0.2786   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745    1.7103   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.7752   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6387    0.9235   -1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253   -1.2548    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9169    0.3305    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -0.6085    2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1298    2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -1.8069   -1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.8677    0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405   -2.3074    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    1.4247    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -1.3505    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    0.2409    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    0.7793    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971   -0.9877    2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2150   -2.4725    0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -1.9110    0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -1.9215   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03759.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.391  -1.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.391  -2.670   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.057  -3.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.723  -2.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.723  -1.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.057  -0.360   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.390  -3.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.944  -2.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.944  -1.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.390  -0.360   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.278  -0.360   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.278   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.944   1.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.390   1.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.742  -0.836   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.647   0.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.742   1.656   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.725  -3.440   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.218   3.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.439   2.712   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.944   0.410   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -1.689   0.376   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.723  -4.210   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.390  -1.900   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       3.129   4.210   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.725   3.441   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.278  -1.900   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   23                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    9    5   14   24                                             
CONECT   11    9   12   15   27                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18    2                                                            
CONECT   19   17   25   26                                                  
CONECT   20   12                                                            
CONECT   21    9                                                            
CONECT   22    5                                                            
CONECT   23    4                                                            
CONECT   24   10                                                            
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0003759
HETATM    1  C1  UNL     1       5.826  -0.521  -0.267  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.395  -0.897  -0.188  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.049  -1.962  -0.605  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.448   0.057   0.403  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.548   1.300  -0.523  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.327   1.033  -1.430  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.345   0.771  -0.366  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.008   0.269  -0.706  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.664   1.321  -1.613  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.037   0.716  -1.929  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.826   0.673  -0.664  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.252   0.251  -0.933  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.005   0.399   0.340  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.072   0.981   0.304  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.406  -0.174   1.572  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.944   0.113   1.700  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.179  -0.169   0.424  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.300  -1.605   0.035  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.779   0.313   0.614  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.091  -0.280   1.772  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.391  -0.175   1.818  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.037  -0.338   0.447  1.00  0.00           C  
HETATM   23  C21 UNL     1       1.673  -1.698  -0.026  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.997   0.538   0.056  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.206  -0.553  -1.326  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.473  -1.234   0.305  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.782   0.361   1.431  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.304   2.177   0.085  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.481   1.330  -1.077  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.562   0.185  -2.071  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.124   1.912  -2.064  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.248   1.676   0.276  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.063  -0.704  -1.190  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.746   2.245  -1.032  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.044   1.401  -2.522  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.588   1.292  -2.669  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.828  -0.279  -2.361  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.875   1.710  -0.261  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.338  -0.775  -1.326  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.639   0.924  -1.725  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.625  -1.255   1.674  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.917   0.330   2.438  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.533  -0.608   2.464  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.725   1.130   2.071  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.033  -1.807  -1.016  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.395  -1.868   0.114  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.740  -2.307   0.664  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.868   1.425   0.818  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.408  -1.351   1.935  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.480   0.241   2.700  1.00  0.00           H  
HETATM   51  H28 UNL     1       1.765   0.779   2.236  1.00  0.00           H  
HETATM   52  H29 UNL     1       1.797  -0.988   2.451  1.00  0.00           H  
HETATM   53  H30 UNL     1       2.215  -2.472   0.574  1.00  0.00           H  
HETATM   54  H31 UNL     1       0.587  -1.911   0.250  1.00  0.00           H  
HETATM   55  H32 UNL     1       1.811  -1.921  -1.076  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   22   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   22   32
CONECT    8    9   19   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   17   38
CONECT   12   13   39   40
CONECT   13   14   14   15
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23
CONECT   23   53   54   55
END

HMDB0003759
     RDKit          3D
5a-Pregnane-3,20-dione
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.8264   -0.5208   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951   -0.8967   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.9621   -0.6054 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483    0.0566    0.4026 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5484    1.2995   -0.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.0331   -1.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452    0.7713   -0.3661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0076    0.2690   -0.7056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6638    1.3210   -1.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372    0.7158   -1.9293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261    0.6731   -0.6644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2516    0.2511   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0047    0.3985    0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0720    0.9814    0.3043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4062   -0.1743    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    0.1126    1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1692    0.4238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2997   -1.6048    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790    0.3131    0.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0914   -0.2804    1.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908   -0.1747    1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -0.3380    0.4470 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6730   -1.6981   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970    0.5378    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2064   -0.5533   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4735   -1.2337    0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7816    0.3609    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3040    2.1773    0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807    1.3297   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5622    0.1846   -2.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1236    1.9123   -2.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484    1.6760    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.7036   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7460    2.2448   -1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.4012   -2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883    1.2920   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -0.2786   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8745    1.7103   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3382   -0.7752   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6387    0.9235   -1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253   -1.2548    1.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9169    0.3305    2.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -0.6085    2.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7249    1.1298    2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -1.8069   -1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.8677    0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7405   -2.3074    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8677    1.4247    0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084   -1.3505    1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    0.2409    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    0.7793    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971   -0.9877    2.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2150   -2.4725    0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5873   -1.9110    0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -1.9215   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,20-Allopregnanedione	ChEBI
3,20-Dioxo-5alpha-pregnane	ChEBI
5-alpha-Dihydroprogesterone	ChEBI
5alpha-Dihydroprogesterone	ChEBI
3,20-Dioxo-5a-pregnane	Generator
3,20-Dioxo-5α-pregnane	Generator
5-a-Dihydroprogesterone	Generator
5-Α-dihydroprogesterone	Generator
5a-Dihydroprogesterone	Generator
5Α-dihydroprogesterone	Generator
5-alpha-Pregnane-3,20-dione	HMDB, MeSH
5a-Pregnan-3,20-dione	HMDB
5alpha-Pregnan-3,20-dione	HMDB
5alpha-Pregnane-3,20-dione	HMDB, MeSH
5b-Pregnane-3,20-dione	HMDB
5beta-Pregnane-3,20-dione	HMDB
Allopregnan-3,20-dione	HMDB
Pregnane-3,20-dione	HMDB
5 alpha Dihydroprogesterone	MeSH, HMDB
5 beta Pregnane 3,20 dione	MeSH, HMDB
5 beta-Pregnane-3,20-dione	MeSH, HMDB
5-beta-Dihydroprogesterone	MeSH, HMDB
5alpha-DHP	MeSH, HMDB
3,20-Allopregnanedione, (5beta,13alpha,17alpha)-isomer	MeSH, HMDB
5 alpha Pregnanedione	MeSH, HMDB
5alpha DHP	MeSH, HMDB
5alpha Pregnane 3,20 dione	MeSH, HMDB
5beta DHP	MeSH, HMDB
5beta-DHP	MeSH, HMDB
3,20 Allopregnanedione	MeSH, HMDB
3,20-Allopregnanedione, (5alpha)-isomer	MeSH, HMDB
5 alpha Pregnane 3,20 dione	MeSH, HMDB
5 alpha-Dihydroprogesterone	MeSH, HMDB
5 alpha-Pregnane-3,20-dione	MeSH, HMDB
5 beta Dihydroprogesterone	MeSH, HMDB
5-alpha-Pregnanedione	MeSH, HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

5a-pregnane-3,20-dione

CAS Registry Number

566-65-4

SMILES

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

InChI Identifier

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

XMRPGKVKISIQBV-BJMCWZGWSA-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-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:28952 )
20-oxo steroid (CHEBI:28952 )
C21-steroid hormone (CHEBI:28952 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030170 )

Ontology

Physiological effect

Health effect

Major depressive disorder (HMDB: HMDB0003759)
Schizophrenia (HMDB: HMDB0003759)
Prepartum depression (HMDB: HMDB0003759)

Disposition

Biological location

Biofluid or Excreta

Urine (HMDB: HMDB0003759)

Non-excretory biofluid

Blood (PMID: 16959481)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003759)

Fibroblasts (HMDB: HMDB0003759)

Tissue substructure

Hepatic tissue (HMDB: HMDB0003759)

Organ

Testis (HMDB: HMDB0003759)

Cellular substructure

Membrane (HMDB: HMDB0003759)
Extracellular (HMDB: HMDB0003759)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003759)

Source

Endogenous

Endogenous (HMDB: HMDB0003759)

Animal

Animal (HMDB: HMDB0003759)

Exogenous

Food

Food (HMDB: HMDB0003759)

Animal origin

Poultry

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

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Lagomorph

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Alcoholism (HMDB: HMDB0003759)

Metabolic pathway

Steroidogenesis (HMDB: HMDB0003759)

Disease pathway

Chemical reaction

Lipid peroxidation (HMDB: HMDB0003759)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0003759)

Cellular process

Cell signaling (HMDB: HMDB0003759)

System process

Reproduction (HMDB: HMDB0003759)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003759)

Molecular messenger

Hormone (HMDB: HMDB0003759)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003759)

Emulsifier (HMDB: HMDB0003759)

Pharmaceutical industry

Biomarker

Prepartum depression (MarkerDB: MDB00000432)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0013 g/L	ALOGPS
logP	4.06	ALOGPS
logP	4.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.34	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.88 m³·mol⁻¹	ChemAxon
Polarizability	37.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.046	31661259
DarkChem	[M-H]-	175.051	31661259
DeepCCS	[M-2H]-	213.802	30932474
DeepCCS	[M+Na]+	188.212	30932474
AllCCS	[M+H]+	181.5	32859911
AllCCS	[M+H-H2O]+	178.6	32859911
AllCCS	[M+NH4]+	184.2	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	187.3	32859911
AllCCS	[M+Na-2H]-	187.7	32859911
AllCCS	[M+HCOO]-	188.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5a-Pregnane-3,20-dione	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C	2700.0	Standard polar	33892256
5a-Pregnane-3,20-dione	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C	2638.5	Standard non polar	33892256
5a-Pregnane-3,20-dione	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C	2859.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5a-Pregnane-3,20-dione,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2796.2	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2729.1	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3108.6	Standard polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2781.6	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2657.1	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3124.2	Standard polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2764.7	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2674.8	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3122.0	Standard polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2782.9	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2733.5	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3215.6	Standard polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2823.8	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2766.4	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3149.9	Standard polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2831.2	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2790.0	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3148.7	Standard polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2794.2	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2757.4	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3243.6	Standard polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2776.7	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2781.7	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3241.1	Standard polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3039.3	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2980.0	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3265.1	Standard polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3020.9	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2854.7	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #2	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3268.1	Standard polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2994.9	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2886.4	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3267.2	Standard polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3040.0	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2996.7	Standard non polar	33892256
5a-Pregnane-3,20-dione,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3354.2	Standard polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3305.5	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3131.9	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3382.1	Standard polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3306.9	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3197.3	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3384.6	Standard polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3301.1	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3123.7	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	3448.0	Standard polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3265.9	Semi standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3187.1	Standard non polar	33892256
5a-Pregnane-3,20-dione,2TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3449.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-MS (Non-derivatized)	splash10-0umu-9810000000-76ef4cf96a30792f4d73	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-MS (Non-derivatized)	splash10-0umu-9810000000-7151501afadd028a99ec	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-MS (Non-derivatized)	splash10-0umu-9810000000-76ef4cf96a30792f4d73	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-MS (Non-derivatized)	splash10-0umu-9810000000-7151501afadd028a99ec	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-EI-TOF (Non-derivatized)	splash10-0f76-4910000000-81546b52d59f9518cb0c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-EI-TOF (Non-derivatized)	splash10-0f76-4910000000-dbf8c4ca357b5f19f54d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5a-Pregnane-3,20-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fkj-0391000000-1964b2faffc1ae5ab9b4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5a-Pregnane-3,20-dione 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 - 5a-Pregnane-3,20-dione 10V, Positive-QTOF	splash10-014i-0159000000-fdffc096796499edd3d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 20V, Positive-QTOF	splash10-05p2-0492000000-3f8a5badfddf1ced4edf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 40V, Positive-QTOF	splash10-052f-2590000000-932901e825351ef60bc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 10V, Negative-QTOF	splash10-014i-0019000000-8848319d0e10bc22bc8c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 20V, Negative-QTOF	splash10-014i-0039000000-04efc7afcedbf957d0ee	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 40V, Negative-QTOF	splash10-006t-1090000000-259e4f493b06ea76a0d6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 10V, Positive-QTOF	splash10-014j-0069000000-c9fab448f80ee78066da	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 20V, Positive-QTOF	splash10-0002-0491000000-c1e83a8609698882ba42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 40V, Positive-QTOF	splash10-0f6x-3920000000-1083c653754015836eb2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 20V, Negative-QTOF	splash10-014i-0049000000-e44dad0db5aa758e4dd5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5a-Pregnane-3,20-dione 40V, Negative-QTOF	splash10-00ls-0091000000-f15b1c3e520b40f7172b	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Fibroblasts
Testis

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
Blood	Detected and Quantified	0.0171 +/- 0.0056 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected and Quantified	0.055 +/- 0.025 uM	Adult (>18 years old)	Both	Normal	16959481	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0239 +/- 0.0084 uM	Adult (>18 years old)	Female	Prepartum depression	11739473	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Blood	Detected and Quantified	0.042 +/- 0.025 uM	Adult (>18 years old)	Both	Psychiatric disorder	16959481	details

Associated Disorders and Diseases

Disease References

Alcoholism
Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Major depressive disorder
Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Prepartum depression
Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]

Associated OMIM IDs

608516 (Major depressive disorder)
181500 (Schizophrenia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023222

KNApSAcK ID

Not Available

Chemspider ID

83782

KEGG Compound ID

C03681

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5%CE%B1-Dihydroprogesterone

METLIN ID

Not Available

PubChem Compound

92810

PDB ID

Not Available

ChEBI ID

28952

Food Biomarker Ontology

Not Available

VMH ID

C03681

MarkerDB ID

MDB00000432

Good Scents ID

Not Available

References

Synthesis Reference

Valenta, Zdenek. Steroid total synthesis and intermediates. U.S. (1975), 14 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Kwan TK, Kraevskaya MA, Makin HL, Trafford DJ, Gower DB: Use of gas chromatographic-mass spectrometric techniques in studies of androst-16-ene and androgen biosynthesis in human testis; cytosolic specific binding of 5alpha-androst-16-en-3-one. J Steroid Biochem Mol Biol. 1997 Jan;60(1-2):137-46. [PubMed:9182868 ]
Zhang J, Ming LJ, Sjovall J, Cook HW, Ridgway ND, Byers DM: Progesterone metabolism in human fibroblasts is independent of P-glycoprotein levels and Niemann-Pick type C disease. J Steroid Biochem Mol Biol. 1999 Sep-Oct;70(4-6):123-31. [PubMed:10622400 ]
Sandow J, Engelbart K, von Rechenberg W: The different mechanisms for suppression of pituitary and testicular function. Med Biol. 1986;63(5-6):192-200. [PubMed:3010006 ]
Jarczok T, Zwirner M, Schindler AE: Progesterone and 5 alpha-pregnane-3,20-dione in human amniotic fluid. Exp Clin Endocrinol. 1987 Mar;89(1):39-47. [PubMed:3595731 ]
Gomez-Sanchez EP, Cox D, Foecking M, Ganjam V, Gomez-Sanchez CE: 11 beta-hydroxysteroid dehydrogenases of the choriocarcinoma cell line JEG-3 and their inhibition by glycyrrhetinic acid and other natural substances. Steroids. 1996 Mar;61(3):110-5. [PubMed:8852827 ]
Chantilis S, Dombroski R, Shackleton CH, Casey ML, MacDonald PC: Metabolism of 5 alpha-dihydroprogesterone in women and men: 3 beta- and 3 alpha-,6 alpha-dihydroxy-5 alpha-pregnan-20-ones are major urinary metabolites. J Clin Endocrinol Metab. 1996 Oct;81(10):3644-9. [PubMed:8855816 ]
Zwirner M, Fawzy MM, Bopp FC, Klemm-Wolfgram E, Handschuh D, Voelter W, Schindler AE: Radioimmunoassay of 5 alpha-pregnane-3,20-dione. A metabolite of placental progesterone. Arch Gynecol. 1983;233(4):229-40. [PubMed:6660916 ]

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-Hydroxy-5b-pregnane-20-one + NAD → 5a-Pregnane-3,20-dione + NADH + Hydrogen Ion	details
3a-Hydroxy-5b-pregnane-20-one + NADP → 5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion	details

Enzyme Details

2. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Enzyme Details

3. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Enzyme Details

4. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Enzyme Details

5. 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

Reactions

5a-Pregnane-3,20-dione + Acceptor → Progesterone + Reduced acceptor	details
Progesterone + NADPH + Hydrogen Ion → 5a-Pregnane-3,20-dione + NADP	details

Showing metabocard for 5a-Pregnane-3,20-dione (HMDB0003759)

MOL for HMDB0003759 (5a-Pregnane-3,20-dione)

3D MOL for HMDB0003759 (5a-Pregnane-3,20-dione)

3D SDF for HMDB0003759 (5a-Pregnane-3,20-dione)

3D-SDF for HMDB0003759 (5a-Pregnane-3,20-dione)

PDB for HMDB0003759 (5a-Pregnane-3,20-dione)

3D PDB for HMDB0003759 (5a-Pregnane-3,20-dione)

SMILES for HMDB0003759 (5a-Pregnane-3,20-dione)

INCHI for HMDB0003759 (5a-Pregnane-3,20-dione)

Structure for HMDB0003759 (5a-Pregnane-3,20-dione)

3D Structure for HMDB0003759 (5a-Pregnane-3,20-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions