NP-MRD: Showing NP-Card for 17a-Hydroxypregnenolone (NP0000122)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:13:00 UTC

NP-MRD ID

NP0000122

Secondary Accession Numbers

None

Natural Product 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>
NP0000122

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

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 Mass

332.4770 Da

Monoisotopic Mass

332.23514 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
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
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 )

Physical Properties

State

Solid

Experimental 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

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

External Links

HMDB ID

HMDB0000363

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030278

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

Good Scents ID

Not Available

References

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 ]
Riepe FG, Mahler P, Sippell WG, Partsch CJ: Longitudinal study of plasma pregnenolone and 17-hydroxypregnenolone in full-term and preterm neonates at birth and during the early neonatal period. J Clin Endocrinol Metab. 2002 Sep;87(9):4301-6. doi: 10.1210/jc.2002-020452. [PubMed:12213889 ]

Showing NP-Card for 17a-Hydroxypregnenolone (NP0000122)

MOL for NP0000122 (17a-Hydroxypregnenolone)

3D MOL for NP0000122 (17a-Hydroxypregnenolone)

3D SDF for NP0000122 (17a-Hydroxypregnenolone)

3D-SDF for NP0000122 (17a-Hydroxypregnenolone)

PDB for NP0000122 (17a-Hydroxypregnenolone)

3D PDB for NP0000122 (17a-Hydroxypregnenolone)

SMILES for NP0000122 (17a-Hydroxypregnenolone)

INCHI for NP0000122 (17a-Hydroxypregnenolone)

Structure for NP0000122 (17a-Hydroxypregnenolone)

3D Structure for NP0000122 (17a-Hydroxypregnenolone)