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

enzymes (7) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-06 15:31:56 UTC

Update Date

2021-09-14 15:40:02 UTC

HMDB ID

HMDB0006762

Secondary Accession Numbers

HMDB0000382
HMDB00382
HMDB06762

Metabolite Identification

Common Name

17alpha,21-Dihydroxypregnenolone

Description

17alpha,21-Dihydroxypregnenolone is an intermediate in the human fetus at midpregnancy that is converted into cortisol (PMID: 4231965 ). It has also been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions. In normal adrenal slices from patients with hypernephroid kidney carcinomas these pathways bypass cholesterol, pregnenolone, and progesterone, and proceed to 21-hydroxypregnenolone (PMID: 6247575 ). 17alpha,21-Dihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 17alpha,21-Dihydroxypregnenolone is the 5th to last step in the synthesis of Cortol and is converted from 17alpha-Hydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.99.10). It is then converted to 11beta,17alpha,21-Trihydroxypregnenolone via the enzyme cytochrome P450 (EC 1.14.15.4).

Structure

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


  Mrv1652311161719222D          

 28 31  0  0  0  0            999 V2000
 2501.0687 2501.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9312 2499.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7899 2497.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3563 2499.9979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7811 2501.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2502.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2100 2501.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0666 2502.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2501.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0687 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2181 2499.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2499.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2498.3447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.2181 2497.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2499.5843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9291 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.9291 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2497.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.3555 2500.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6410 2500.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0700 2499.5930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0700 2500.4181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7811 2500.8314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.4956 2499.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2500.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 26  6  1  0  0  0  0
 26 10  1  6  0  0  0
 26 25  1  0  0  0  0
 24 27  1  0  0  0  0
 24 11  1  6  0  0  0
 25  1  1  1  0  0  0
 14  3  1  1  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 23 16  1  0  0  0  0
 21 24  1  0  0  0  0
 16  4  1  6  0  0  0
 21  5  1  1  0  0  0
 17  2  1  1  0  0  0
M  END

HMDB0006762
     RDKit          3D
17alpha,21-Dihydroxypregnenolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.0408   -1.7721    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.2870   -0.1318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3718    0.2007   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.4504   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059    0.1622   -0.2727 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1685    0.0134    1.0619 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8179    1.0945    1.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.0329    1.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    0.3912    0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260    0.4328    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.7270   -0.5055 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3418    0.6817   -0.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3902   -0.3664   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -0.0669   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219   -0.3440   -0.2233 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2273   -1.8409    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.3623    1.0358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1081   -0.1194    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    0.0065    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    0.2547    0.1307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4754    1.6376   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4784   -0.4202   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -1.6314   -0.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884    0.3415   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2609    1.7136   -1.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -2.1727    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.2892   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932   -2.0918    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721   -0.0507   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504    1.2934   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.2304   -2.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480   -1.5314   -1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    1.2574   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675   -0.9454    1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.0403    2.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.0778    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    1.5625    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767   -0.6063    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7906    1.1878    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498    1.7140   -0.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.2223    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.3221   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.3965   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.7040   -2.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.0160   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025   -1.9851    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3264   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482   -2.3103   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    1.4608    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -1.1919    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    0.4860    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979   -0.9308    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704    0.8383    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047    1.9878   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5204    0.1677   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978   -0.0161   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    2.0351   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  6
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END


  Mrv1652311161719222D          

 28 31  0  0  0  0            999 V2000
 2501.0687 2501.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9312 2499.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7899 2497.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3563 2499.9979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7811 2501.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2502.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2100 2501.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0666 2502.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2501.2487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0687 2498.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2181 2499.5823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2499.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5036 2498.3447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.2181 2497.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2499.5843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9291 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2498.9291 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6436 2497.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2498.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3581 2499.1718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.3555 2500.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6410 2500.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0700 2499.5930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.0700 2500.4181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7811 2500.8314    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.4956 2499.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4956 2500.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6  9  2  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 28  1  0  0  0  0
 26  6  1  0  0  0  0
 26 10  1  6  0  0  0
 26 25  1  0  0  0  0
 24 27  1  0  0  0  0
 24 11  1  6  0  0  0
 25  1  1  1  0  0  0
 14  3  1  1  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 23 16  1  0  0  0  0
 21 24  1  0  0  0  0
 16  4  1  6  0  0  0
 21  5  1  1  0  0  0
 17  2  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006762

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1

> <INCHI_KEY>
JNHJGXQUDOYJAK-IYRCEVNGSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.63040943997079

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <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]-2-hydroxyethan-1-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.016685283666667

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.905650428318339

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.591023870838399

> <JCHEM_PKA_STRONGEST_BASIC>
-1.397243740261139

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
96.85889999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-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]-2-hydroxyethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006762
     RDKit          3D
17alpha,21-Dihydroxypregnenolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.0408   -1.7721    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.2870   -0.1318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3718    0.2007   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.4504   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059    0.1622   -0.2727 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1685    0.0134    1.0619 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8179    1.0945    1.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.0329    1.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    0.3912    0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260    0.4328    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.7270   -0.5055 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3418    0.6817   -0.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3902   -0.3664   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -0.0669   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219   -0.3440   -0.2233 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2273   -1.8409    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.3623    1.0358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1081   -0.1194    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    0.0065    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    0.2547    0.1307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4754    1.6376   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4784   -0.4202   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -1.6314   -0.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884    0.3415   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2609    1.7136   -1.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -2.1727    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.2892   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932   -2.0918    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721   -0.0507   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504    1.2934   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.2304   -2.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480   -1.5314   -1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    1.2574   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675   -0.9454    1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.0403    2.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.0778    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    1.5625    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767   -0.6063    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7906    1.1878    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498    1.7140   -0.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.2223    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.3221   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.3965   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.7040   -2.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.0160   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025   -1.9851    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3264   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482   -2.3103   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    1.4608    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -1.1919    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    0.4860    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979   -0.9308    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704    0.8383    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047    1.9878   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5204    0.1677   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978   -0.0161   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    2.0351   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  6
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 16-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-17         0                                  
HETATM    1  C   UNK     0    4668.6624668.994   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.6724666.663   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    4660.6744662.803   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    4666.0014664.358   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    4667.3324666.663   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    4669.9914669.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.3254670.538   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4672.6594669.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4668.6584670.538   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    4671.3254668.998   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0    4668.6624664.358   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    4663.3404665.887   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4662.0074665.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4662.0074663.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4663.3404662.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4666.0014665.891   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4664.6684665.121   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4664.6684663.581   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    4666.0014662.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    4667.3354663.581   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    4667.3354665.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4667.3304668.217   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    4665.9974667.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    4668.6644665.907   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    4668.6644667.447   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    4669.9914668.219   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    4671.3254665.909   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    4671.3254667.449   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   17                                                            
CONECT    3   14                                                            
CONECT    4   16                                                            
CONECT    5   21                                                            
CONECT    6    7    9   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10   26                                                            
CONECT   11   24                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    3                                                  
CONECT   15   14   18                                                       
CONECT   16   17   21   23    4                                             
CONECT   17   16   18   12    2                                             
CONECT   18   17   19   15                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   16   20   24    5                                             
CONECT   22   23   25                                                       
CONECT   23   22   16                                                       
CONECT   24   25   27   11   21                                             
CONECT   25   22   24   26    1                                             
CONECT   26   28    6   10   25                                             
CONECT   27   28   24                                                       
CONECT   28   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0006762
HETATM    1  C1  UNL     1      -2.041  -1.772   0.018  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.022  -0.287  -0.132  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.372   0.201  -1.372  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.019  -0.450  -1.401  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.806   0.162  -0.273  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.168   0.013   1.062  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.818   1.095   1.941  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.294   1.033   1.820  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.933   0.391   0.849  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.426   0.433   0.882  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.951   0.727  -0.505  1.00  0.00           C  
HETATM   12  O1  UNL     1       6.342   0.682  -0.455  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.390  -0.366  -1.398  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.924  -0.067  -1.556  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.222  -0.344  -0.223  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.227  -1.841   0.041  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.293   0.362   1.036  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.108  -0.119   2.174  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.535   0.007   1.626  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.401   0.255   0.131  1.00  0.00           C  
HETATM   21  O2  UNL     1      -3.475   1.638  -0.032  1.00  0.00           O  
HETATM   22  C20 UNL     1      -4.478  -0.420  -0.613  1.00  0.00           C  
HETATM   23  O3  UNL     1      -4.589  -1.631  -0.610  1.00  0.00           O  
HETATM   24  C21 UNL     1      -5.488   0.342  -1.406  1.00  0.00           C  
HETATM   25  O4  UNL     1      -5.261   1.714  -1.326  1.00  0.00           O  
HETATM   26  H1  UNL     1      -1.071  -2.173   0.411  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.288  -2.289  -0.919  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.793  -2.092   0.769  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.872  -0.051  -2.306  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.150   1.293  -1.258  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.538  -0.230  -2.341  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.148  -1.531  -1.292  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.873   1.257  -0.499  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.367  -0.945   1.575  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.464   1.040   2.978  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.504   2.078   1.492  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.889   1.562   2.599  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.777  -0.606   1.136  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.791   1.188   1.574  1.00  0.00           H  
HETATM   40  H15 UNL     1       4.650   1.714  -0.856  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.618   1.222   0.329  1.00  0.00           H  
HETATM   42  H17 UNL     1       4.612  -1.322  -0.891  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.915  -0.397  -2.371  1.00  0.00           H  
HETATM   44  H19 UNL     1       2.523  -0.704  -2.360  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.827   1.016  -1.751  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.602  -1.985   1.073  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.866  -2.326  -0.717  1.00  0.00           H  
HETATM   48  H23 UNL     1       1.248  -2.310  -0.024  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.390   1.461   0.899  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.902  -1.192   2.359  1.00  0.00           H  
HETATM   51  H26 UNL     1      -1.990   0.486   3.097  1.00  0.00           H  
HETATM   52  H27 UNL     1      -4.098  -0.931   1.792  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.070   0.838   2.128  1.00  0.00           H  
HETATM   54  H29 UNL     1      -3.005   1.988  -0.804  1.00  0.00           H  
HETATM   55  H30 UNL     1      -6.520   0.168  -1.027  1.00  0.00           H  
HETATM   56  H31 UNL     1      -5.498  -0.016  -2.460  1.00  0.00           H  
HETATM   57  H32 UNL     1      -5.726   2.035  -0.514  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   17   20
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   15   33
CONECT    6    7   17   34
CONECT    7    8   35   36
CONECT    8    9    9   37
CONECT    9   10   15
CONECT   10   11   38   39
CONECT   11   12   13   40
CONECT   12   41
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   15   16
CONECT   16   46   47   48
CONECT   17   18   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   22
CONECT   21   54
CONECT   22   23   23   24
CONECT   24   25   55   56
CONECT   25   57
END

HMDB0006762
     RDKit          3D
17alpha,21-Dihydroxypregnenolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.0408   -1.7721    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -0.2870   -0.1318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3718    0.2007   -1.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -0.4504   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059    0.1622   -0.2727 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1685    0.0134    1.0619 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8179    1.0945    1.9407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.0329    1.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    0.3912    0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4260    0.4328    0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.7270   -0.5055 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3418    0.6817   -0.4546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3902   -0.3664   -1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239   -0.0669   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219   -0.3440   -0.2233 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2273   -1.8409    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2930    0.3623    1.0358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1081   -0.1194    2.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5348    0.0065    1.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006    0.2547    0.1307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4754    1.6376   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4784   -0.4202   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894   -1.6314   -0.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4884    0.3415   -1.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2609    1.7136   -1.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708   -2.1727    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.2892   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7932   -2.0918    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721   -0.0507   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1504    1.2934   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.2304   -2.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480   -1.5314   -1.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    1.2574   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675   -0.9454    1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4637    1.0403    2.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038    2.0778    1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892    1.5625    2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767   -0.6063    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7906    1.1878    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6498    1.7140   -0.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.2223    0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6123   -1.3221   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9152   -0.3965   -2.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.7040   -2.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    1.0160   -1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6025   -1.9851    1.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -2.3264   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2482   -2.3103   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897    1.4608    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -1.1919    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9898    0.4860    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979   -0.9308    1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704    0.8383    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0047    1.9878   -0.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5204    0.1677   -1.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4978   -0.0161   -2.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7264    2.0351   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  6
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17a,21-Dihydroxypregnenolone	Generator
17Α,21-dihydroxypregnenolone	Generator
17alpha,21-Dihydroxypreg-nenolone	HMDB
17, 21-Dihydroxypregnenolone	HMDB
3Β,17α,21-trihydroxypregnenone	HMDB
3beta,17alpha,21-Trihydroxypregnenone	HMDB
17,21-Dihydroxypregnenolone	HMDB
3Β,17,21-trihydroxy-pregn-5-en-20-one	HMDB
3beta,17,21-Trihydroxy-pregn-5-en-20-one	HMDB
(3Β)-3,17,21-trihydroxypregn-5-en-20-one	HMDB
(3beta)-3,17,21-Trihydroxypregn-5-en-20-one	HMDB
3Β,17α,21-trihydroxypregn-5-en-20-one	HMDB
3beta,17alpha,21-Trihydroxypregn-5-en-20-one	HMDB
17alpha,21-Dihydroxypregnenolone	HMDB

Chemical Formula

C₂₁H₃₂O₄

Average Molecular Weight

348.4764

Monoisotopic Molecular Weight

348.230059512

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]-2-hydroxyethan-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]-2-hydroxyethanone

CAS Registry Number

1167-48-2

SMILES

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

InChI Identifier

InChI=1S/C21H32O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h3,14-17,22-23,25H,4-12H2,1-2H3/t14-,15+,16-,17-,19-,20-,21-/m0/s1

InChI Key

JNHJGXQUDOYJAK-IYRCEVNGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Oxosteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
17-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:27832 )
17alpha-hydroxy steroid (CHEBI:27832 )
21-hydroxy steroid (CHEBI:27832 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030141 )

Ontology

Disposition

Biological location

Cellular substructure

Extracellular

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Steroidogenesis

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	10^(2.6) g/L	ALOGPS
logP	10^(2.02) g/L	ChemAxon
logS	10^(-3.8) g/L	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.86 m³·mol⁻¹	ChemAxon
Polarizability	39.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.426	31661259
DarkChem	[M-H]-	178.707	31661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17alpha,21-Dihydroxypregnenolone,1TMS,#1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO	3144.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TMS,#2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C	3112.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TMS,#3	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO	3124.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TMS,#4	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C	3025.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO	3161.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3193.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#3	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3100.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#4	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C	3146.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#5	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3072.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TMS,#6	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C	3033.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TMS,#1	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3201.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TMS,#2	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3097.9	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TMS,#3	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3185.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TMS,#4	C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3078.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TBDMS,#1	CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3409.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TBDMS,#2	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3413.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TBDMS,#3	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@](O)(C(=O)CO)[C@@]4(C)CC[C@@H]32)C1	3388.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,1TBDMS,#4	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3307.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#1	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3745.2	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#2	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)[C@@]4(C)CC[C@@H]32)C1	3679.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#3	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3647.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#4	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3688.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#5	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3607.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,2TBDMS,#6	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3544.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TBDMS,#1	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3960.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TBDMS,#2	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C	3959.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TBDMS,#3	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3852.1	Semi standard non polar	https://arxiv.org/abs/1905.12712
17alpha,21-Dihydroxypregnenolone,3TBDMS,#4	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C	3818.4	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-4189000000-38652a1384b510a4e849	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone GC-MS (3 TMS) - 70eV, Positive	splash10-0f6t-1111090000-ac64327581e7c755d285	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,21-Dihydroxypregnenolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Positive-QTOF	splash10-001j-0029000000-0868a1856a2a865dc2da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Positive-QTOF	splash10-01qa-0097000000-873e4eef53be76546e5f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Positive-QTOF	splash10-00xr-0491000000-bf3679c3178ebe5ceb4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Negative-QTOF	splash10-0002-0029000000-5f642a89fae11d677fda	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Negative-QTOF	splash10-05bs-3098000000-d61819020861e0a89cf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Negative-QTOF	splash10-0a4i-6091000000-8a9828ddf7d9d4a69ef6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Negative-QTOF	splash10-0002-0019000000-b815dac004fdf0d56944	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Negative-QTOF	splash10-00kk-1096000000-5d0fda6d923e4716d986	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Negative-QTOF	splash10-000i-0090000000-a4cb9cce30a71598a761	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 10V, Positive-QTOF	splash10-0002-0009000000-4e7f285caeb4129cd706	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 20V, Positive-QTOF	splash10-01xw-0911000000-08a13dee014c9e27e8d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,21-Dihydroxypregnenolone 40V, Positive-QTOF	splash10-00os-2930000000-32c88edb904f52d77158	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024065

KNApSAcK ID

Not Available

Chemspider ID

167253

KEGG Compound ID

C05487

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

192735

PDB ID

Not Available

ChEBI ID

27832

Food Biomarker Ontology

Not Available

VMH ID

M00406

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Heer, J.; Miescher, K. Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series. Helvetica Chimica Acta (1951), 34 359-72.

Material Safety Data Sheet (MSDS)

Not Available

General References

Pasqualini JR, Lowy J, Wiqvist N, Diczfalusy E: Biosynthesis of cortisol from 3 beta, 17 alpha,21-trihydroxypregn-5-en-20-one by the intact human foetus at midpregnancy. Biochim Biophys Acta. 1968 May 1;152(3):648-50. [PubMed:4231965 ]
Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [PubMed:6247575 ]

Enzymes

Enzyme Details

1. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

Reactions

17alpha,21-Dihydroxypregnenolone + Reduced ferredoxin + Oxygen → 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Water	details

Enzyme Details

2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

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

Reactions

Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NAD	details

Enzyme Details

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

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

Reactions

Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NAD	details

Enzyme Details

4. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

Reactions

17alpha,21-Dihydroxypregnenolone + Reduced ferredoxin + Oxygen → 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Water	details

Enzyme Details

5. Cytochrome P450 21-hydroxylase

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

Enzyme Details

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

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

Enzyme Details

7. Steroid 21-hydroxylase

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

Reactions

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

Showing metabocard for 17alpha,21-Dihydroxypregnenolone (HMDB0006762)

MOL for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

3D MOL for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

3D SDF for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

3D-SDF for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

PDB for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

3D PDB for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

SMILES for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

INCHI for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

Structure for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

3D Structure for HMDB0006762 (17alpha,21-Dihydroxypregnenolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

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