MiMeDB: Showing metabocard for 17a-Hydroxypregnenolone (MMDBc0047908)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:14:25 UTC

Update Date

2022-09-01 02:01:11 UTC

Metabolite ID

MMDBc0047908

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>
MMDBc0047908

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₂₁H₃₂O₃

Average Mass

332.477

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-054x-4900000000-df86d10979d808f20e67	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-2891000000-3605ad7dd57f97382115	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ff0-3792000000-974e157d4c25e376b004	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-054x-4900000000-df86d10979d808f20e67	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-3295000000-48ed11374901b134a70d	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03di-0111900000-e55e71b4d8c63cde89c2	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0039000000-28c103ca6cdf072557bf	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0900000000-ae3004bb674d9632cd0c	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-0900000000-a2f467560b451d5c9b0e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0f89-2891000000-82e62584fff36943bcba	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0029000000-131b75950fb7123106d9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0094000000-2a48017855d3965d5626	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g29-2690000000-3d1b2b0525a2f6da149c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-4c286aa6d88850e66ba9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008i-0098000000-77ce542de402b225ac27	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avr-0092000000-e39f57cc01b46a017728	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-08a5ce4022cbdbf8bfa1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0029000000-8619dcbabe228085742a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0091000000-4088584830d78ccb6fb2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0029000000-275368791dddb24379f9	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-0910000000-b08f322c49579d81e79a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1940000000-1f423724847a658c9f85	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biospecimen Locations

Adrenal Cortex
Blood
Feces
Testis

Tissue Locations

Adrenal Cortex
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192362	Cholesterol side-chain cleavage enzyme, mitochondrial	Unknown	P05108	Homo sapiens
MMDBp0192653	Steroid 17-alpha-hydroxylase/17,20 lyase	Unknown	P05093	Homo sapiens
MMDBp0193970	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1	Unknown	P14060	Homo sapiens
MMDBp0193971	3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2	Unknown	P26439	Homo sapiens
MMDBp0194155	Cytochrome P450 21-hydroxylase	Enzyme	Q16874	Homo sapiens
MMDBp0195936	Cytochrome P450, family 21, subfamily A, polypeptide 2	Enzyme	Q08AG9	Homo sapiens
MMDBp0196723	Steroid 21-hydroxylase	Unknown	P08686

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001478	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Not Available	3 Beta-Hydroxysteroid Dehydrogenase/Delta 5->4-Isomerase Type I	VMH	12205101
MMDBr0001479	17a-Hydroxypregnenolone	17-Hydroxyprogesterone	Hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 2	3 Beta-Hydroxysteroid Dehydrogenase/Delta 5->4-Isomerase Type I	VMH	12205101
MMDBr0001844	Hydrogen Ion	17a-Hydroxypregnenolone	Cytochrome p450, family 17, subfamily a, polypeptide 1	Cytochrome P450 17A1	VMH	7893148
MMDBr0001845	17a-Hydroxypregnenolone	Acetaldehyde	Cytochrome p450, family 17, subfamily a, polypeptide 1	Cytochrome P450 17A1	VMH	12915666 7893148
MMDBr0003949	17Alpha-Hydroxypregnenolone Sulfate	17a-Hydroxypregnenolone	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003950	17Alpha-Hydroxypregnenolone Sulfate	17a-Hydroxypregnenolone	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003951	17Alpha-Hydroxypregnenolone Sulfate	17a-Hydroxypregnenolone	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003952	17Alpha-Hydroxypregnenolone Sulfate	17a-Hydroxypregnenolone	Steroid sulfatase (microsomal), isozyme s	Steryl-Sulfatase	VMH	10049998 1606923
MMDBr0003957	17a-Hydroxypregnenolone	Acetic acid	Not Available	RE1134C	VMH	10049998 7578007
MMDBr0003958	17a-Hydroxypregnenolone	Acetic acid	Cytochrome p450, family 17, subfamily a, polypeptide 1	RE1134M	VMH	10049998 7578007
MMDBr0003959	17a-Hydroxypregnenolone	Acetic acid	Cytochrome p450, family 17, subfamily a, polypeptide 1	RE1134R	VMH	10049998 7578007
MMDBr0008859	17a-Hydroxypregnenolone	17a-Hydroxypregnenolone	Atp binding cassette subfamily b member 1	Transport of 17Alpha-Hydroxypregnenolone, Extracellular	VMH	30371894
MMDBr0009613	Hydrogen Ion	17a-Hydroxypregnenolone	Cytochrome p450, family 17, subfamily a, polypeptide 1	Steroid 17Alpha-Monooxygenase	VMH	30371894
MMDBr0009614	17a-Hydroxypregnenolone	Water	Cytochrome p450, family 21, subfamily a, polypeptide 2	17Alpha-Hydroxypregnenolone, Hydrogen-Donor:Oxygen Oxidoreductase (21-Hydroxylating)	VMH	30371894
MMDBr0009617	17a-Hydroxypregnenolone	Acetaldehyde	Cytochrome p450, family 17, subfamily a, polypeptide 1	17Alpha-Hydroxypregnenolone Acetaldehyde-Lyase	VMH	30371894
MMDBr0009618	17a-Hydroxypregnenolone	17Alpha-Hydroxypregnenolone Sulfate	Sulfotransferase family, cytosolic, 2b, member 1	Alcohol Sulfotransferase	VMH	30371894
MMDBr0009625	17a-Hydroxypregnenolone	Hydrogen Ion	Hydroxy-delta-5-steroid dehydrogenase, 3 beta- and steroid delta-isomerase 1	3Beta-Hydroxy-Delta5-Steroid Dehydrogenase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	0.0186				uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	7951484
Human Blood	Detected and Quantified	0.159				uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human Blood	Detected and Quantified	0.741				uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	26079780
Human 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	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	26079780
Human 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	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	12050224
Human 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	HMDB	26079780
Human 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	HMDB	26079780
Human Blood	Detected and Quantified	0.000271				uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448
Human Blood	Detected and Quantified	0.00123				uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	HMDB	18182448
Human Blood	Detected and Quantified			0.0120	0.180	uM	Infant (0-1 year old)	Both	Antley-Bixler syndrome with genital anomalies and disordered steroidogenesis	HMDB	16439592
Human Blood	Detected and Quantified			0.000300	0.0240	uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	16439592
Human Blood	Detected and Quantified	0.000782	0.000993			uM	Children (1-13 years old)	Both	Normal	HMDB	26079780
Human Blood	Detected and Quantified			0.00180	0.00451	uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified			0.00211	0.0256	uM	Newborn (0-30 days old)	Female	Normal	HMDB	18182448
Human Blood	Detected and Quantified	0.003		0.000	0.006	uM	Adult (>18 years old)	Female	Normal	HMDB	16777916
Human Blood	Detected and Quantified	0.006		0.001	0.012	uM	Adult (>18 years old)	Male	Normal	HMDB	16777916
Human Blood	Detected and Quantified	0.00656	0.00562			uM	Children (1-13 years old)	Both	Normal	HMDB	26079780
Human Blood	Detected and Quantified	0.00902	0.00361			uM	Adult (>18 years old)	Female	Normal	HMDB	7951484
Human Adrenal cortex	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0000363

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1530/acta.0.0870400. [PubMed:580138 ]
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. doi: 10.1507/endocrj1954.35.189. [PubMed:3208699 ]
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. doi: 10.1210/jcem-57-1-32. [PubMed:6853680 ]
Miller WL: Androgen biosynthesis from cholesterol to DHEA. Mol Cell Endocrinol. 2002 Dec 30;198(1-2):7-14. doi: 10.1016/s0303-7207(02)00363-5. [PubMed:12573809 ]

Showing metabocard for 17a-Hydroxypregnenolone (MMDBc0047908)

MOL for #<Metabolite:0x00007fe2ac3ba740>

3D MOL for #<Metabolite:0x00007fe2ac3ba740>

3D SDF for #<Metabolite:0x00007fe2ac3ba740>

3D-SDF for #<Metabolite:0x00007fe2ac3ba740>

PDB for #<Metabolite:0x00007fe2ac3ba740>

3D PDB for #<Metabolite:0x00007fe2ac3ba740>

SMILES for #<Metabolite:0x00007fe2ac3ba740>

INCHI for #<Metabolite:0x00007fe2ac3ba740>

Structure for #<Metabolite:0x00007fe2ac3ba740>

3D Structure for #<Metabolite:0x00007fe2ac3ba740>