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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:42 UTC

HMDB ID

HMDB0000363

Secondary Accession Numbers

HMDB00363

Metabolite Identification

Common Name

17a-Hydroxypregnenolone

Description

17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (PMID: 12573809 ).

Structure

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


  Mrv1652305261923532D          

 27 30  0  0  1  0            999 V2000
    7.6473  -11.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6473  -11.8401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3617  -12.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -11.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -11.0151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3617  -10.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907  -12.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -11.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -11.0151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7907  -10.6026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2197  -10.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2197   -9.7776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5052   -9.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907   -9.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0043  -10.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4892  -10.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0043   -9.5227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9328  -12.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -10.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3059   -8.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2593   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -10.1901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907  -11.4277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8191   -9.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7072   -8.1249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0662   -8.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3059  -11.4231    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  2  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  1  1  0  0  0
  5 19  1  1  0  0  0
 12 20  1  1  0  0  0
 17 21  1  1  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
 17 24  1  6  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END

HMDB0000363
     RDKit          3D
17a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.4506    1.1316    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386    0.6972   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6879    1.1409   -1.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -0.2555    0.0397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4315   -0.6714    1.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434   -1.5193   -0.8072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925   -2.0023   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224   -1.0797   -0.0825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1293   -0.9517   -0.3572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8290   -2.1759    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.9484    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.7893    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.7329    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6667    1.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0509    0.6808    1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.5966    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    1.6856    0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    0.3812   -0.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1698    0.3364   -1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835    0.2398    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0898    1.4966    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240    1.2307    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2335   -0.3179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0163    0.6584   -1.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7783    2.1706    0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9349    1.0332    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3206    0.4240    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9493   -1.5347    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.3520   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278   -2.3184   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495   -1.8453   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -3.0638   -0.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.3557    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.9081   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -3.0222   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2363   -2.5659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -2.8248    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.2990    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -1.2430    0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.0561    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3831    0.0802    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992    2.5916    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    1.1489   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550    2.4895   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    1.8569    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.8858   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.8656   -1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492   -0.6974   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    0.0025    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    1.8214   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730    2.2979    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    2.1572    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    0.7368    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.7602   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512    0.4154   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    0.1869   -2.3812 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  1
  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  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  6
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  1
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END


  Mrv1652305261923532D          

 27 30  0  0  1  0            999 V2000
    7.6473  -11.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6473  -11.8401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3617  -12.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -11.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -11.0151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3617  -10.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907  -12.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -11.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -11.0151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7907  -10.6026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2197  -10.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2197   -9.7776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5052   -9.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907   -9.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0043  -10.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4892  -10.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0043   -9.5227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9328  -12.2526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0762  -10.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3059   -8.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2593   -8.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -10.1901    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7907  -11.4277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8191   -9.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7072   -8.1249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0662   -8.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3059  -11.4231    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  2  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  1  1  0  0  0
  5 19  1  1  0  0  0
 12 20  1  1  0  0  0
 17 21  1  1  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
 17 24  1  6  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 11 27  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000363

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

> <INCHI_KEY>
JERGUCIJOXJXHF-TVWVXWENSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.477

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.65617201917503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
2.8339333296666673

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.613197522108244

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699631740725032

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972436501688699

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
95.15669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000363
     RDKit          3D
17a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.4506    1.1316    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386    0.6972   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6879    1.1409   -1.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -0.2555    0.0397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4315   -0.6714    1.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434   -1.5193   -0.8072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925   -2.0023   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224   -1.0797   -0.0825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1293   -0.9517   -0.3572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8290   -2.1759    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.9484    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.7893    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.7329    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6667    1.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0509    0.6808    1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.5966    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    1.6856    0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    0.3812   -0.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1698    0.3364   -1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835    0.2398    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0898    1.4966    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240    1.2307    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2335   -0.3179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0163    0.6584   -1.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7783    2.1706    0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9349    1.0332    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3206    0.4240    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9493   -1.5347    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.3520   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278   -2.3184   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495   -1.8453   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -3.0638   -0.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.3557    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.9081   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -3.0222   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2363   -2.5659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -2.8248    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.2990    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -1.2430    0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.0561    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3831    0.0802    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992    2.5916    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    1.1489   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550    2.4895   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    1.8569    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.8858   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.8656   -1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492   -0.6974   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    0.0025    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    1.8214   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730    2.2979    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    2.1572    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    0.7368    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.7602   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512    0.4154   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    0.1869   -2.3812 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  1
  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  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  6
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  1
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      14.275 -20.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.275 -22.102   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.609 -22.872   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.942 -22.102   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.942 -20.562   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.609 -19.792   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.276 -22.872   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.610 -22.102   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.610 -20.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.276 -19.792   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.943 -19.792   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.943 -18.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.610 -17.482   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.276 -18.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.408 -20.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.313 -19.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.408 -17.776   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.941 -22.872   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.942 -19.022   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.104 -16.720   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.884 -16.311   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      19.610 -19.022   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      18.276 -21.332   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      23.929 -17.535   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      21.853 -15.166   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      24.390 -15.991   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      21.104 -21.323   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                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   22                                             
CONECT   10    9    5   14   23                                             
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   21   24                                             
CONECT   18    2                                                            
CONECT   19    5                                                            
CONECT   20   12                                                            
CONECT   21   17   25   26                                                  
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   17                                                            
CONECT   25   21                                                            
CONECT   26   21                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0000363
HETATM    1  C1  UNL     1      -5.451   1.132   0.840  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.539   0.697  -0.242  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.688   1.141  -1.358  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.473  -0.255   0.040  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.431  -0.671   1.365  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.543  -1.519  -0.807  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.092  -2.002  -0.958  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.322  -1.080  -0.082  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.129  -0.952  -0.357  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.829  -2.176   0.147  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.198  -1.948   0.623  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.845  -0.789   0.557  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.221  -0.733   1.082  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.670   0.667   1.419  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.051   0.681   1.444  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.219   1.597   0.298  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.712   1.686   0.405  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.135   0.381  -0.045  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.170   0.336  -1.557  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.683   0.240   0.373  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.090   1.497   0.171  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.524   1.231   0.630  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.087   0.234  -0.318  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.016   0.658  -1.760  1.00  0.00           C  
HETATM   25  H1  UNL     1      -5.778   2.171   0.766  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.935   1.033   1.838  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.321   0.424   0.912  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.949  -1.535   1.440  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.015  -1.352  -1.784  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.128  -2.318  -0.293  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.750  -1.845  -2.016  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.024  -3.064  -0.690  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.544  -1.356   0.980  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.284  -0.908  -1.454  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.785  -3.022  -0.599  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.236  -2.566   1.026  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.702  -2.825   1.063  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.215  -1.299   2.059  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.967  -1.243   0.439  1.00  0.00           H  
HETATM   40  H16 UNL     1       4.244   1.056   2.348  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.383   0.080   0.733  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.699   2.592   0.384  1.00  0.00           H  
HETATM   43  H19 UNL     1       4.571   1.149  -0.638  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.355   2.490  -0.270  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.438   1.857   1.461  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.057   0.886  -1.975  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.288   0.866  -1.973  1.00  0.00           H  
HETATM   48  H24 UNL     1       2.249  -0.697  -1.954  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.680   0.002   1.454  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.153   1.821  -0.883  1.00  0.00           H  
HETATM   51  H27 UNL     1       0.373   2.298   0.745  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.108   2.157   0.703  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.424   0.737   1.626  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.134   1.760  -1.844  1.00  0.00           H  
HETATM   55  H31 UNL     1      -1.051   0.415  -2.245  1.00  0.00           H  
HETATM   56  H32 UNL     1      -2.818   0.187  -2.381  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5    6   23
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   23   33
CONECT    9   10   20   34
CONECT   10   11   35   36
CONECT   11   12   12   37
CONECT   12   13   18
CONECT   13   14   38   39
CONECT   14   15   16   40
CONECT   15   41
CONECT   16   17   42   43
CONECT   17   18   44   45
CONECT   18   19   20
CONECT   19   46   47   48
CONECT   20   21   49
CONECT   21   22   50   51
CONECT   22   23   52   53
CONECT   23   24
CONECT   24   54   55   56
END

HMDB0000363
     RDKit          3D
17a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.4506    1.1316    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5386    0.6972   -0.2420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6879    1.1409   -1.3576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4734   -0.2555    0.0397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4315   -0.6714    1.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434   -1.5193   -0.8072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0925   -2.0023   -0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224   -1.0797   -0.0825 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1293   -0.9517   -0.3572 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8290   -2.1759    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1980   -1.9484    0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447   -0.7893    0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.7329    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697    0.6667    1.4186 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0509    0.6808    1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.5966    0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115    1.6856    0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    0.3812   -0.0452 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1698    0.3364   -1.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835    0.2398    0.3733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0898    1.4966    0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240    1.2307    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    0.2335   -0.3179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0163    0.6584   -1.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7783    2.1706    0.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9349    1.0332    1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3206    0.4240    0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9493   -1.5347    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0153   -1.3520   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278   -2.3184   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7495   -1.8453   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -3.0638   -0.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -1.3557    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835   -0.9081   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -3.0222   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2363   -2.5659    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7022   -2.8248    1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155   -1.2990    2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9670   -1.2430    0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2440    1.0561    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3831    0.0802    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6992    2.5916    0.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5714    1.1489   -0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3550    2.4895   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384    1.8569    1.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    0.8858   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2879    0.8656   -1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2492   -0.6974   -1.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6802    0.0025    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1529    1.8214   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3730    2.2979    0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    2.1572    0.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243    0.7368    1.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1340    1.7602   -1.8444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0512    0.4154   -2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8176    0.1869   -2.3812 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  1
  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  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  1
  9 34  1  6
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  1
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  1
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta)-3,17-Dihydroxypregn-5-en-20-one	ChEBI
17-Hydroxypregnenolone	ChEBI
5-Pregnen-3beta,17alpha-diol-20-one	ChEBI
(3b)-3,17-Dihydroxypregn-5-en-20-one	Generator
(3Β)-3,17-dihydroxypregn-5-en-20-one	Generator
5-Pregnen-3b,17a-diol-20-one	Generator
5-Pregnen-3β,17α-diol-20-one	Generator
17-Hydroxy-D5-pregnenolone	HMDB
17-OH-Pregnenolone	HMDB
17a-Hydroxypregnolone	HMDB
17alpha-Hydroxypregnanolone	HMDB
17alpha-Hydroxypregnenolone	HMDB
3b,17-Dihydroxy-5-pregnen-20-one	HMDB
3b,17-Dihydroxy-pregn-5-en-20-one	HMDB
3b,17a-Dihydroxypregn-5-en-20-one	HMDB
17alpha Hydroxypregnenolone	HMDB
Hydroxypregnenolone	HMDB
17 Hydroxypregnenolone	HMDB
17 alpha Hydroxypregnenolone	HMDB
17-Hydroxypregnenolone, (3alpha)-isomer	HMDB
17-Hydroxypregnenolone, (3beta,13alpha)-isomer	HMDB
17-alpha-Hydroxypregnenolone	HMDB
17 alpha-Hydroxypregnenolone	HMDB
17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomer	HMDB
17-Hydroxypregnenolone, (3beta,17alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₂O₃

Average Molecular Weight

332.477

Monoisotopic Molecular Weight

332.23514489

IUPAC Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

Traditional Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

CAS Registry Number

387-79-1

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

InChI Key

JERGUCIJOXJXHF-TVWVXWENSA-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-hydroxy-delta-5-steroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28750 )
17alpha-hydroxy steroid (CHEBI:28750 )
hydroxypregnenolone (CHEBI:28750 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030089 )

Ontology

Not Available

Adrenal Cortex (HMDB: HMDB0000363)

Organ

Testis (HMDB: HMDB0000363)
Testicle (HMDB: HMDB0000363)

Gland

Endocrine gland

Adrenal cortex (HMDB: HMDB0000363)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16777916)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000363)

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Androgen and Estrogen Metabolism (HMDB: HMDB0000363)
Steroidogenesis (HMDB: HMDB0000363)

Disease pathway

17-beta Hydroxysteroid Dehydrogenase III Deficiency (PathBank: SMP0000356)
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency (PathBank: SMP0000373)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (PathBank: SMP0000371)
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency (PathBank: SMP0000372)
Aromatase Deficiency (PathBank: SMP0000565)
17-alpha-Hydroxylase Deficiency (CYP17) (PathBank: SMP0000566)
11-beta-Hydroxylase Deficiency (CYP11B1) (PathBank: SMP0000575)
21-Hydroxylase Deficiency (CYP21) (PathBank: SMP0000576)
Corticosterone Methyl Oxidase I Deficiency (CMO I) (PathBank: SMP0000577)
Corticosterone Methyl Oxidase II Deficiency (CMO II) (PathBank: SMP0000578)
Apparent Mineralocorticoid Excess Syndrome (PathBank: SMP0000717)
3-beta-Hydroxysteroid Dehydrogenase Deficiency (PathBank: SMP0000718)

Role

Biological role

human metabolite (HMDB: HMDB0000363)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	266 - 271 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	190.452	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001970

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	3.15	ALOGPS
logP	2.83	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.16 m³·mol⁻¹	ChemAxon
Polarizability	38.66 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.259	31661259
DarkChem	[M-H]-	174.328	31661259
AllCCS	[M+H]+	184.578	32859911
AllCCS	[M-H]-	188.97	32859911
DeepCCS	[M-2H]-	211.868	30932474
DeepCCS	[M+Na]+	186.221	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.8	32859911
AllCCS	[M+NH4]+	187.1	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	189.0	32859911
AllCCS	[M+Na-2H]-	189.5	32859911
AllCCS	[M+HCOO]-	190.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2657.7	Standard polar	33892256
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2730.6	Standard non polar	33892256
17a-Hydroxypregnenolone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C	2873.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17a-Hydroxypregnenolone,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2934.1	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2913.3	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2827.9	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2961.6	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	2958.2	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2855.0	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2964.5	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	2904.0	Standard non polar	33892256
17a-Hydroxypregnenolone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3228.3	Standard polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3183.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3170.5	Semi standard non polar	33892256
17a-Hydroxypregnenolone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3115.1	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3457.9	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3503.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3385.0	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3724.7	Semi standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3605.8	Standard non polar	33892256
17a-Hydroxypregnenolone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3481.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (1 MEOX; 2 TMS)	splash10-054x-4900000000-df86d10979d808f20e67	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (1 MEOX; 2 TMS)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone EI-B (Non-derivatized)	splash10-0f89-2891000000-3605ad7dd57f97382115	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone EI-B (Non-derivatized)	splash10-0ff0-3792000000-974e157d4c25e376b004	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (Non-derivatized)	splash10-054x-4900000000-df86d10979d808f20e67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (Non-derivatized)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-3295000000-48ed11374901b134a70d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (2 TMS) - 70eV, Positive	splash10-03di-0111900000-e55e71b4d8c63cde89c2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17a-Hydroxypregnenolone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17a-Hydroxypregnenolone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-001i-0039000000-28c103ca6cdf072557bf	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17a-Hydroxypregnenolone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-0900000000-ae3004bb674d9632cd0c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17a-Hydroxypregnenolone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-0900000000-a2f467560b451d5c9b0e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17a-Hydroxypregnenolone EI-B (HITACHI M-52) , Positive-QTOF	splash10-0f89-2891000000-82e62584fff36943bcba	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 10V, Positive-QTOF	splash10-0159-0029000000-131b75950fb7123106d9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 20V, Positive-QTOF	splash10-015i-0094000000-2a48017855d3965d5626	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 40V, Positive-QTOF	splash10-0g29-2690000000-3d1b2b0525a2f6da149c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 10V, Negative-QTOF	splash10-001i-0009000000-4c286aa6d88850e66ba9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 20V, Negative-QTOF	splash10-008i-0098000000-77ce542de402b225ac27	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 40V, Negative-QTOF	splash10-0avr-0092000000-e39f57cc01b46a017728	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 10V, Negative-QTOF	splash10-001i-0009000000-08a5ce4022cbdbf8bfa1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 20V, Negative-QTOF	splash10-001i-0029000000-8619dcbabe228085742a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 40V, Negative-QTOF	splash10-000i-0091000000-4088584830d78ccb6fb2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 10V, Positive-QTOF	splash10-00lr-0029000000-275368791dddb24379f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 20V, Positive-QTOF	splash10-014m-0910000000-b08f322c49579d81e79a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17a-Hydroxypregnenolone 40V, Positive-QTOF	splash10-0002-1940000000-1f423724847a658c9f85	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Cortex
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00180-0.00451 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00211-0.0256 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00902 +/- 0.00361 uM	Adult (>18 years old)	Female	Normal	7951484	details
Blood	Detected and Quantified	0.000300-0.0240 uM	Infant (0-1 year old)	Not Specified	Normal	16439592	details
Blood	Detected and Quantified	0.000782 +/- 0.000993 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.00656 +/- 0.00562 uM	Children (1-13 years old)	Both	Normal	26079780	details
Blood	Detected and Quantified	0.003 (0.000 - 0.006) uM	Adult (>18 years old)	Female	Normal	16777916	details
Blood	Detected and Quantified	0.006 (0.001-0.012) uM	Adult (>18 years old)	Male	Normal	16777916	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000271 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.00123 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Blood	Detected and Quantified	0.0126 +/- 0.0105 uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00440 +/- 0.00280 uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.159 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.741 uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0264-0.103 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0843-1.262 uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00230 +/- 0.00200 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00300 +/- 0.00250 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00380 +/- 0.00210 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00896 +/- 0.00770 uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0186 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.0120-0.180 uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	16439592	details
Blood	Detected and Quantified	0.136 +/- 0.129 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.00439 +/- 0.00896 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.176 +/- 0.186 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Blood	Detected and Quantified	0.0111 +/- 0.0219 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	26079780	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ] Benkert AR, Young M, Robinson D, Hendrickson C, Lee PA, Strauss KA: Severe Salt-Losing 3beta-Hydroxysteroid Dehydrogenase Deficiency: Treatment and Outcomes of HSD3B2 c.35G>A Homozygotes. J Clin Endocrinol Metab. 2015 Aug;100(8):E1105-15. doi: 10.1210/jc.2015-2098. Epub 2015 Jun 16. [PubMed:26079780 ]
Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis
Fukami M, Hasegawa T, Horikawa R, Ohashi T, Nishimura G, Homma K, Ogata T: Cytochrome P450 oxidoreductase deficiency in three patients initially regarded as having 21-hydroxylase deficiency and/or aromatase deficiency: diagnostic value of urine steroid hormone analysis. Pediatr Res. 2006 Feb;59(2):276-80. doi: 10.1203/01.pdr.0000195825.31504.28. [PubMed:16439592 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]

Associated OMIM IDs

201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
201750 (Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021982

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

17-Hydroxypregnenolone

METLIN ID

5352

PubChem Compound

91451

PDB ID

Not Available

ChEBI ID

28750

Food Biomarker Ontology

Not Available

VMH ID

17AHPRGNLONE

MarkerDB ID

MDB00000153

Good Scents ID

Not Available

References

Synthesis Reference

Kaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin. Preparation from their esters of steroid alcohols that are sensitive to acids and alkali. (1958), DE 1028572 19580424 CAN 54:74845 AN 1960:74845 CAPLUS

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Shimozawa K, Saisho S, Yata J, Kambegawa A: Age-related changes in serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in human infancy and childhood. Endocrinol Jpn. 1988 Apr;35(2):189-95. [PubMed:3208699 ]
Rodriguez-Rigau LJ, Weiss DB, Smith KD, Steinberger E: Suggestion of abnormal testicular steroidogenesis in some oligospermic men. Acta Endocrinol (Copenh). 1978 Feb;87(2):400-12. [PubMed:580138 ]
Kaufman FR, Costin G, Goebelsmann U, Stanczyk FZ, Zachmann M: Male pseudohermaphroditism due to 17,20-desmolase deficiency. J Clin Endocrinol Metab. 1983 Jul;57(1):32-6. [PubMed:6853680 ]
Miller WL: Androgen biosynthesis from cholesterol to DHEA. Mol Cell Endocrinol. 2002 Dec 30;198(1-2):7-14. [PubMed:12573809 ]

Enzymes

Enzyme Details

1. Cholesterol side-chain cleavage enzyme, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:: CYP11A1
Uniprot ID:: P05108
Molecular weight:: 60101.87

Reactions

17a,20a-Dihydroxycholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin → 17a-Hydroxypregnenolone + 4-Methylpentanal + Water + Oxidized adrenal ferredoxin	details

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

Reactions

Pregnenolone + Reduced acceptor + Oxygen → 17a-Hydroxypregnenolone + Acceptor + Water	details
17a-Hydroxypregnenolone + Reduced acceptor + Oxygen → Dehydroepiandrosterone + Acetic acid + Acceptor + Water	details

Enzyme Details

3. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Ion	details

Enzyme Details

4. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

17a-Hydroxypregnenolone + NAD → 17-Hydroxyprogesterone + NADH + Hydrogen Ion	details

Enzyme Details

5. Cytochrome P450 21-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: P450-CYP21B
Uniprot ID:: Q16874
Molecular weight:: 56000.9

Enzyme Details

6. Cytochrome P450, family 21, subfamily A, polypeptide 2

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP21A2
Uniprot ID:: Q08AG9
Molecular weight:: 55972.9

Enzyme Details

7. Steroid 21-hydroxylase

General function:: Not Available
Specific function:: Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:: CYP21A2
Uniprot ID:: P08686
Molecular weight:: 56000.94

Reactions

17a-Hydroxypregnenolone + NADPH + Hydrogen Ion + Oxygen → 17alpha,21-Dihydroxypregnenolone + NADP + Water	details

Showing metabocard for 17a-Hydroxypregnenolone (HMDB0000363)

MOL for HMDB0000363 (17a-Hydroxypregnenolone)

3D MOL for HMDB0000363 (17a-Hydroxypregnenolone)

3D SDF for HMDB0000363 (17a-Hydroxypregnenolone)

3D-SDF for HMDB0000363 (17a-Hydroxypregnenolone)

PDB for HMDB0000363 (17a-Hydroxypregnenolone)

3D PDB for HMDB0000363 (17a-Hydroxypregnenolone)

SMILES for HMDB0000363 (17a-Hydroxypregnenolone)

INCHI for HMDB0000363 (17a-Hydroxypregnenolone)

Structure for HMDB0000363 (17a-Hydroxypregnenolone)

3D Structure for HMDB0000363 (17a-Hydroxypregnenolone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

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