NP-MRD: Showing NP-Card for 16-a-Hydroxypregnenolone (NP0000256)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:14:04 UTC

NP-MRD ID

NP0000256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-a-Hydroxypregnenolone

Description

16-Alpha-hydroxypregnenolone, also known as (3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one, is classified as a gluco/mineralocorticoid, a progestogin or aprogestogin derivative. Gluco/mineralocorticoids are steroids with a structure based on a hydroxylated prostane moiety. Thus, 16-alpha-hydroxypregnenolone is a steroid lipid molecule. 16-Alpha-hydroxypregnenolone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-Alpha-hydroxypregnenolone can be found primarily in blood, urine and in human umbilical cord tissue. Within the cell, 16-alpha-hydroxypregnenolone is primarily located in the membrane, and in the nucleus bound to cytoplasmic glucocorticoid receptors. 16-Alpha-hydroxypregnenolone exists in all vertebrates. 16-A-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency (PMID 6980322 ).

Structure

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


  Mrv1652305261923522D          

 27 30  0  0  1  0            999 V2000
   12.5242   -8.3594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3292   -9.4428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8383   -9.5720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6004   -6.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0556   -8.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2024   -7.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8534  -10.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5505  -10.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6615   -9.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7527   -8.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3586   -8.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4499   -7.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4256  -10.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0084   -8.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1769   -6.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1228  -10.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950  -10.1535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5170   -9.2130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7863   -8.8299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2141   -8.7718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4658   -8.3080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9541   -7.6608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0892   -9.2711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1806   -7.9474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9763   -6.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9979  -10.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2901   -8.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  0  0  0  0
 23  5  1  1  0  0  0
 24  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  2  0  0  0  0
 18  8  1  0  0  0  0
  9 17  1  0  0  0  0
  9 11  1  0  0  0  0
 19 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 21  1  0  0  0  0
 20 14  1  0  0  0  0
 15 25  2  0  0  0  0
 22 15  1  1  0  0  0
 16 23  1  0  0  0  0
 17 26  1  1  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 27  1  6  0  0  0
 22 24  1  0  0  0  0
 19  3  1  6  0  0  0
 20  2  1  6  0  0  0
 18  1  1  1  0  0  0
M  END

HMDB0000315
     RDKit          3D
16-a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.6458    2.0741   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882    0.7252    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    0.4555    1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -0.2139   -0.1627 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5290   -1.5484    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5640   -2.3526    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657   -2.1658    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -1.1132   -0.3423 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -0.9948    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7865   -2.2514   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -2.0663   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.8904    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482   -0.7884    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -0.0565   -0.6889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8320    0.8301   -0.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    0.6101   -1.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670    1.3898   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.4008    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224    1.0303    1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    0.1544   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0969    1.4159   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.2435   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    0.1805    0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9312    0.4712    1.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3277    2.0348   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    2.4035   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    2.8662    0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.3771   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.2737    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -2.6011    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -2.5376    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2880   -3.0308   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4376   -1.1517   -1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -0.9733    1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -3.1486    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -2.2852   -1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9692   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6474   -1.8177    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574   -0.2818    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4499   -0.8170   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6948    1.7579   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470    1.3162   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.1703   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    1.9709   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    2.0795   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    0.7900    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647    0.6157    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    2.1381    1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9231   -0.1568   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940    2.1000    0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.9879   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    2.2432   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872    1.0206   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    1.4385    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.3485    2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.6377    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 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
  4 28  1  6
  5 29  1  1
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  6
 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  6
 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


  Mrv1652305261923522D          

 27 30  0  0  1  0            999 V2000
   12.5242   -8.3594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3292   -9.4428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8383   -9.5720    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6004   -6.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0556   -8.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2024   -7.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8534  -10.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5505  -10.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6615   -9.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7527   -8.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3586   -8.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4499   -7.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4256  -10.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0084   -8.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1769   -6.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1228  -10.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6950  -10.1535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5170   -9.2130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7863   -8.8299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2141   -8.7718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4658   -8.3080    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9541   -7.6608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.0892   -9.2711    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1806   -7.9474    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.9763   -6.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9979  -10.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2901   -8.2745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4 15  1  0  0  0  0
 23  5  1  1  0  0  0
 24  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7 16  2  0  0  0  0
 18  8  1  0  0  0  0
  9 17  1  0  0  0  0
  9 11  1  0  0  0  0
 19 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 21  1  0  0  0  0
 20 14  1  0  0  0  0
 15 25  2  0  0  0  0
 22 15  1  1  0  0  0
 16 23  1  0  0  0  0
 17 26  1  1  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  1  0  0  0  0
 21 22  1  0  0  0  0
 21 27  1  6  0  0  0
 22 24  1  0  0  0  0
 19  3  1  6  0  0  0
 20  2  1  6  0  0  0
 18  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0000256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](O)[C@H](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/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
ZAKJZPQDUPCXSD-YRWKUUEZSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.477

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.92163096222343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.350547385666667

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.204289505503816

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.750568179059915

> <JCHEM_PKA_STRONGEST_BASIC>
-1.397243343576704

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
95.27219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000315
     RDKit          3D
16-a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.6458    2.0741   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882    0.7252    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    0.4555    1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -0.2139   -0.1627 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5290   -1.5484    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5640   -2.3526    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657   -2.1658    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -1.1132   -0.3423 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -0.9948    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7865   -2.2514   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -2.0663   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.8904    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482   -0.7884    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -0.0565   -0.6889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8320    0.8301   -0.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    0.6101   -1.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670    1.3898   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.4008    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224    1.0303    1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    0.1544   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0969    1.4159   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.2435   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    0.1805    0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9312    0.4712    1.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3277    2.0348   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    2.4035   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    2.8662    0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.3771   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.2737    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -2.6011    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -2.5376    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2880   -3.0308   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4376   -1.1517   -1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -0.9733    1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -3.1486    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -2.2852   -1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9692   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6474   -1.8177    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574   -0.2818    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4499   -0.8170   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6948    1.7579   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470    1.3162   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.1703   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    1.9709   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    2.0795   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    0.7900    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647    0.6157    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    2.1381    1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9231   -0.1568   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940    2.1000    0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.9879   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    2.2432   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872    1.0206   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    1.4385    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.3485    2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.6377    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 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
  4 28  1  6
  5 29  1  1
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  6
 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  6
 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  H   UNK     0      23.379 -15.604   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      24.881 -17.627   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      22.098 -17.868   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      25.387 -11.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.637 -15.767   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.644 -13.254   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.126 -19.560   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.428 -18.736   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.035 -17.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.938 -14.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.336 -16.591   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.240 -14.120   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.461 -19.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.149 -16.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.464 -12.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.763 -18.845   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.097 -18.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.365 -17.198   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.001 -16.482   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.666 -16.374   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.003 -15.508   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      26.048 -14.300   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.700 -17.306   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.604 -14.835   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      27.956 -12.436   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      16.796 -19.777   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      28.542 -15.446   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3   19                                                            
CONECT    4   15                                                            
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7    8   16                                                       
CONECT    8    7   18                                                       
CONECT    9   17   11                                                       
CONECT   10   19   12                                                       
CONECT   11    9   23                                                       
CONECT   12   10   24                                                       
CONECT   13   16   17                                                       
CONECT   14   21   20                                                       
CONECT   15    4   25   22                                                  
CONECT   16    7   13   23                                                  
CONECT   17    9   13   26                                                  
CONECT   18    8   20   19    1                                             
CONECT   19   10   18   23    3                                             
CONECT   20   14   18   24    2                                             
CONECT   21   14   22   27                                                  
CONECT   22   15   21   24                                                  
CONECT   23    5   11   16   19                                             
CONECT   24    6   12   20   22                                             
CONECT   25   15                                                            
CONECT   26   17                                                            
CONECT   27   21                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0000315
HETATM    1  C1  UNL     1       4.646   2.074  -0.151  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.488   0.725   0.450  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.171   0.456   1.423  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.515  -0.214  -0.163  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.529  -1.548   0.605  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.564  -2.353   0.193  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.166  -2.166   0.353  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.387  -1.113  -0.342  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.047  -0.995   0.062  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.787  -2.251  -0.425  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.213  -2.066  -0.092  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.769  -0.890   0.110  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.248  -0.788   0.449  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.895  -0.056  -0.689  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.832   0.830  -0.172  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.894   0.610  -1.587  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.867   1.390  -0.779  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.041   0.401   0.029  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.922   1.030   1.420  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.697   0.154  -0.604  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.097   1.416  -0.652  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.571   1.243  -0.811  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.072   0.181   0.089  1.00  0.00           C  
HETATM   24  C21 UNL     1       1.931   0.471   1.544  1.00  0.00           C  
HETATM   25  H1  UNL     1       4.328   2.035  -1.212  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.708   2.404  -0.158  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.111   2.866   0.433  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.706  -0.377  -1.240  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.570  -1.274   1.675  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.107  -2.601   0.984  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.705  -2.538   1.290  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.288  -3.031  -0.337  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.438  -1.152  -1.441  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.205  -0.973   1.144  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.372  -3.149   0.071  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.613  -2.285  -1.530  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.823  -2.969  -0.013  1.00  0.00           H  
HETATM   38  H14 UNL     1      -4.647  -1.818   0.585  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.357  -0.282   1.428  1.00  0.00           H  
HETATM   40  H16 UNL     1      -5.450  -0.817  -1.296  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.695   1.758  -0.481  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.447   1.316  -2.248  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.428  -0.170  -2.212  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.267   1.971  -1.475  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.450   2.080  -0.134  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.926   0.790   1.836  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.665   0.616   2.124  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.966   2.138   1.346  1.00  0.00           H  
HETATM   49  H25 UNL     1      -0.923  -0.157  -1.665  1.00  0.00           H  
HETATM   50  H26 UNL     1      -0.094   2.100   0.201  1.00  0.00           H  
HETATM   51  H27 UNL     1      -0.241   1.988  -1.567  1.00  0.00           H  
HETATM   52  H28 UNL     1       2.036   2.243  -0.571  1.00  0.00           H  
HETATM   53  H29 UNL     1       1.887   1.021  -1.849  1.00  0.00           H  
HETATM   54  H30 UNL     1       1.377   1.438   1.730  1.00  0.00           H  
HETATM   55  H31 UNL     1       1.461  -0.348   2.133  1.00  0.00           H  
HETATM   56  H32 UNL     1       2.922   0.638   2.013  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   23   28
CONECT    5    6    7   29
CONECT    6   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

HMDB0000315
     RDKit          3D
16-a-Hydroxypregnenolone
 56 59  0  0  0  0  0  0  0  0999 V2000
    4.6458    2.0741   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882    0.7252    0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1710    0.4555    1.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -0.2139   -0.1627 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5290   -1.5484    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5640   -2.3526    0.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1657   -2.1658    0.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3869   -1.1132   -0.3423 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -0.9948    0.0623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7865   -2.2514   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126   -2.0663   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7695   -0.8904    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2482   -0.7884    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -0.0565   -0.6889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8320    0.8301   -0.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941    0.6101   -1.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8670    1.3898   -0.7785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    0.4008    0.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9224    1.0303    1.4198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6972    0.1544   -0.6035 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0969    1.4159   -0.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.2435   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    0.1805    0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9312    0.4712    1.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3277    2.0348   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    2.4035   -0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1110    2.8662    0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7064   -0.3771   -1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.2737    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1071   -2.6011    0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -2.5376    1.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2880   -3.0308   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4376   -1.1517   -1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -0.9733    1.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3717   -3.1486    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -2.2852   -1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8226   -2.9692   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6474   -1.8177    0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574   -0.2818    1.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4499   -0.8170   -1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6948    1.7579   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470    1.3162   -2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279   -0.1703   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666    1.9709   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496    2.0795   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9260    0.7900    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6647    0.6157    2.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9663    2.1381    1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9231   -0.1568   -1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0940    2.1000    0.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412    1.9879   -1.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0358    2.2432   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8872    1.0206   -1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3769    1.4385    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4609   -0.3485    2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9222    0.6377    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  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  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 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
  4 28  1  6
  5 29  1  1
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  6
 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  6
 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

Synonyms

Value	Source
(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-one	ChEBI
16-alpha-Hydroxypregnenolone	ChEBI
(3b,16a)-3,16-Dihydroxypregn-5-en-20-one	Generator
(3Β,16α)-3,16-dihydroxypregn-5-en-20-one	Generator
16-Α-hydroxypregnenolone	Generator
16 alpha-Hydroxypregnenolone	HMDB
16-a-Hydroxy-pregnenolone	HMDB
16-alpha-Hydroxy-pregnenolone	HMDB
16alpha-Hydroxypregnenolone	HMDB
3b,16a-Dihydroxypreg-5-en-20-one	HMDB
3b,16a-Dihydroxypregn-5-en-20-one	HMDB
3b,16a-Dihydroxypregnen-5-en-20-one	HMDB
5-Pregnene-3b,16a-diol-20-one	HMDB
Pregn-5-en-3b,16a-diol-20-one	HMDB
3 alpha,16 alpha-Dihydroxypregn-5-en-20-one	HMDB
3 beta,16 alpha-Dihydroxypregn-5-en-20-one	HMDB
3 beta,16 beta-Dihydroxypregn-5-en-20-one	HMDB
16a-Hydroxypregnenolone	HMDB
16Α-hydroxypregnenolone	HMDB
16-a-Hydroxypregnenolone	Generator

Chemical Formula

C₂₁H₃₂O₃

Average Mass

332.4770 Da

Monoisotopic Mass

332.23514 Da

IUPAC Name

1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-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,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

CAS Registry Number

520-88-7

SMILES

[H][C@@]12C[C@@H](O)[C@H](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/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1

InChI Key

ZAKJZPQDUPCXSD-YRWKUUEZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
3-beta-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:771 )
16alpha-hydroxy steroid (CHEBI:771 )
hydroxypregnenolone (CHEBI:771 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030172 )

Physical Properties

State

Solid

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.75	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	95.27 m³·mol⁻¹	ChemAxon
Polarizability	38.92 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

External Links

HMDB ID

HMDB0000315

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021942

KNApSAcK ID

Not Available

Chemspider ID

4955002

KEGG Compound ID

C06390

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5304

PubChem Compound

6452574

PDB ID

Not Available

ChEBI ID

771

Good Scents ID

Not Available

References

General References

Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. [PubMed:668632 ]
Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
Den K, Haruyama T, Hagiwara H, Fujii KT, Kambegawa A, Takami T, Yoshida T, Takagi S: Plasma levels of 16 alpha-hydroxypregnenolone, 16 alpha-hydroxyprogesterone and 16 alpha-hydroxydehydroepiandrosterone in the fetus and neonates. Endocrinol Jpn. 1979 Aug;26(4):439-47. doi: 10.1507/endocrj1954.26.439. [PubMed:159171 ]
Janoski AH, Kelly WG: On the metabolism of 16-alpha-hydroxy-C21-steroids. II. Evidence for the presence of a glucuronide of 16-alpha-hydroxypregnenolone in human urine and its utility in estimating the rates of production of 16-alpha-hydroxyprogesterone and 16-alpha-hydroxypregnenolone. J Clin Endocrinol Metab. 1969 Oct;29(10):1291-300. doi: 10.1210/jcem-29-10-1291. [PubMed:5353659 ]

Showing NP-Card for 16-a-Hydroxypregnenolone (NP0000256)

MOL for NP0000256 (16-a-Hydroxypregnenolone)

3D MOL for NP0000256 (16-a-Hydroxypregnenolone)

3D SDF for NP0000256 (16-a-Hydroxypregnenolone)

3D-SDF for NP0000256 (16-a-Hydroxypregnenolone)

PDB for NP0000256 (16-a-Hydroxypregnenolone)

3D PDB for NP0000256 (16-a-Hydroxypregnenolone)

SMILES for NP0000256 (16-a-Hydroxypregnenolone)

INCHI for NP0000256 (16-a-Hydroxypregnenolone)

Structure for NP0000256 (16-a-Hydroxypregnenolone)

3D Structure for NP0000256 (16-a-Hydroxypregnenolone)