NP-MRD: Showing NP-Card for Dehydroepiandrosterone (NP0000667)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:03 UTC

NP-MRD ID

NP0000667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydroepiandrosterone

Description

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.

Structure

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

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END


  Mrv1652303182019232D          

 24 27  0  0  0  0            999 V2000
 9999.306610000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447910001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4479 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1658 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.733710000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5937 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5937 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.734610001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.020110000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0201 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7346 9999.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3067 9999.3661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.3067 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7357 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.233810000.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.449210000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4491 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2337 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.718610000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488710001.6517    0.0000 O   0  0  0  0  0  0  0  0  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9  4  1  1  0  0  0
  7 15  1  0  0  0  0
 10 16  1  0  0  0  0
 15  1  1  1  0  0  0
 13 15  1  0  0  0  0
 18 14  1  0  0  0  0
 14  5  1  1  0  0  0
 13  6  1  6  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  2  0  0  0  0
 11 20  1  0  0  0  0
 14 21  1  0  0  0  0
 20  2  1  1  0  0  0
 21  3  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000667

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
FMGSKLZLMKYGDP-USOAJAOKSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.099316668638735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.361705055333334

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957705855663583

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505502594

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972434077338853

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.65889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.3728667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3698669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3698664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3768663.164   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8668.0368667.030   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.7078664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8664.0428666.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7088665.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7088663.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0428663.173   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.0388668.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.7048667.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7048666.269   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0388665.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3738665.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3738663.943   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.7068663.173   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.0408663.943   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.8368668.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3728667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3728666.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.8368665.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7418667.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8671.3128669.750   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    9                                                            
CONECT    5   14                                                            
CONECT    6   13                                                            
CONECT    7    8   15                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    4                                                  
CONECT   10    9   16                                                       
CONECT   11   12   20                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15    6                                             
CONECT   14   13   18    5   21                                             
CONECT   15   16    7    1   13                                             
CONECT   16   15   17   10                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   20   23   24                                                  
CONECT   20   19   21   11    2                                             
CONECT   21   20   22   14    3                                             
CONECT   22   21   23                                                       
CONECT   23   19   22                                                       
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0000077
HETATM    1  C1  UNL     1      -2.788   0.189  -1.446  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.694   0.623  -0.000  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.912   1.866   0.197  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.496   1.680  -0.243  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.150   0.426   0.224  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.752  -0.790   0.128  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.078  -1.992   0.691  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.400  -1.914   0.698  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.114  -0.967   0.131  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.596  -0.964   0.185  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.136   0.351   0.709  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.273   0.704   0.007  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.109   1.459   0.590  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.319   1.320  -0.674  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.393   0.131  -0.585  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.085  -0.312  -1.989  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.012  -0.455   0.858  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.021  -1.538   0.927  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.366  -0.815   0.804  1.00  0.00           C  
HETATM   20  C19 UNL     1      -4.040   0.618   0.568  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.760   1.538   0.808  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.922  -0.910  -1.527  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.952   0.590  -2.017  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.732   0.637  -1.855  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.337   2.706  -0.417  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.955   2.161   1.249  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.092   2.541   0.188  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.458   1.828  -1.339  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.448   0.513   1.288  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.963  -0.953  -0.962  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.344  -2.870   0.046  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.482  -2.248   1.704  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.912  -2.732   1.231  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.010  -1.124  -0.831  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.957  -1.755   0.863  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.400   0.275   1.789  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.080   0.701   0.602  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.463   1.405   1.473  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.655   2.430   0.547  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.015   1.117  -1.519  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.773   2.239  -0.927  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.721  -1.349  -2.043  1.00  0.00           H  
HETATM   43  H22 UNL     1       2.053  -0.246  -2.566  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.381   0.336  -2.510  1.00  0.00           H  
HETATM   45  H24 UNL     1      -1.758   0.005   1.821  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.988  -1.969   1.968  1.00  0.00           H  
HETATM   47  H26 UNL     1      -2.902  -2.321   0.162  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.833  -1.193  -0.121  1.00  0.00           H  
HETATM   49  H28 UNL     1      -4.991  -0.969   1.703  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9    9   33
CONECT    9   10   15
CONECT   10   11   34   35
CONECT   11   12   13   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   21
END

HMDB0000077
     RDKit          3D
Dehydroepiandrosterone
 49 52  0  0  0  0  0  0  0  0999 V2000
   -2.7875    0.1894   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.6234   -0.0001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9123    1.8657    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4957    1.6798   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1499    0.4258    0.2241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516   -0.7895    0.1280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0782   -1.9921    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.9136    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1141   -0.9674    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5964   -0.9638    0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1358    0.3507    0.7088 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2732    0.7035    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086    1.4592    0.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.3198   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    0.1313   -0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0846   -0.3122   -1.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -0.4554    0.8577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0207   -1.5378    0.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8149    0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0403    0.6177    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.5383    0.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9216   -0.9102   -1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522    0.5902   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.6367   -1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    2.7059   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9555    2.1606    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920    2.5411    0.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    1.8276   -1.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    0.5132    1.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627   -0.9531   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436   -2.8698    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4821   -2.2484    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -2.7323    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100   -1.1239   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572   -1.7553    0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000    0.2745    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0795    0.7007    0.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629    1.4051    1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553    2.4295    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0151    1.1167   -1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729    2.2389   -0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211   -1.3490   -2.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0527   -0.2462   -2.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3814    0.3356   -2.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7581    0.0052    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -1.9685    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -2.3211    0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8331   -1.1927   -0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9911   -0.9691    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-BETA-HYDROXY-5-androsten-17-one	ChEBI
3beta-Hydroxyandrost-5-en-17-one	ChEBI
Dehydroisoandrosterone	ChEBI
DHA	ChEBI
DHEA	ChEBI
Intrarosa	ChEBI
Prasterone	ChEBI
Biolaif	Kegg
3-b-HYDROXY-5-androsten-17-one	Generator
3-Β-hydroxy-5-androsten-17-one	Generator
3b-Hydroxyandrost-5-en-17-one	Generator
3Β-hydroxyandrost-5-en-17-one	Generator
(+)-Dehydroisoandrosterone	HMDB
(3-beta)-3-Hydroxyandrost-5-en-17-one	HMDB
(3beta)-3-Hydroxy-androst-5-en-17-one	HMDB
(3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one	HMDB
17-Chetovis	HMDB
17-Hormoforin	HMDB
3-beta-Hydroxyandrost-5-en-17-one	HMDB
3b-Hydroxy-D5-androsten-17-one	HMDB
3beta-Hydroxy-5-androsten-17-one	HMDB
3beta-Hydroxy-androst-5-en-17-one	HMDB
3beta-Hydroxy-D5-androsten-17-one	HMDB
5,6-Dehydroisoandrosterone	HMDB
5,6-Didehydroisoandrosterone	HMDB
5-Androsten-3-beta-ol-17-one	HMDB
5-Androsten-3b-ol-17-one	HMDB
5-Androsten-3beta-ol-17-one	HMDB
5-Dehydro-epiandrosterone	HMDB
5-Dehydroepiandrosterone	HMDB
Andrestenol	HMDB
Androst-5-ene-3b-ol-17-one	HMDB
Androst-5-ene-3beta-ol-17-one	HMDB
Androsten-3beta-ol-17-one	HMDB
Androstenolone	HMDB
Astenile	HMDB
D5-Androsten-3b-ol-17-one	HMDB
D5-Androsten-3beta-ol-17-one	HMDB
Deandros	HMDB
Dehydro-epi-androsterone	HMDB
Diandron	HMDB
Diandrone	HMDB
Hydroxyandrostenone	HMDB
Prasterona	HMDB
Prasteronum	HMDB
Prestara	HMDB
Psicosterone	HMDB
trans-Dehydroandrosterone	HMDB
Prasterone, 3 alpha-isomer	HMDB
5 Androsten 3 beta hydroxy 17 one	HMDB
5-Androsten-3-beta-hydroxy-17-one	HMDB
5 Androsten 3 ol 17 one	HMDB
Prasterone, 3 alpha isomer	HMDB
5-Androsten-3-ol-17-one	HMDB
EM-760Dehydroandrosterone	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4244 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

53-43-0

SMILES

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

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

FMGSKLZLMKYGDP-USOAJAOKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, 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	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, 50 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	¹³C NMR Spectrum (1D, 226 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

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
Streptomyces nigra	LOTUS Database	35616633
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 androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28689 )
17-oxo steroid (CHEBI:28689 )
androstanoid (CHEBI:28689 )
C19 steroids (androgens) and derivatives (C01227 )
Androstane and derivatives (C01227 )
Androgens (C01227 )
C19 steroids (androgens) and derivatives (LMST02020021 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	140 - 141 °C	Not Available
Boiling Point	426.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.064 mg/mL	Not Available
LogP	3.23	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	3.53	ALOGPS
logP	3.36	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.66 m³·mol⁻¹	ChemAxon
Polarizability	34.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000077

DrugBank ID

DB01708

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021808

KNApSAcK ID

Not Available

Chemspider ID

5670

KEGG Compound ID

C01227

BioCyc ID

3-BETA-HYDROXYANDROST-5-EN-17-ONE

BiGG ID

37131

Wikipedia Link

Dehydroepiandrosterone

METLIN ID

5133

PubChem Compound

5881

PDB ID

Not Available

ChEBI ID

28689

Good Scents ID

rw1133221

References

General References

Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8. [PubMed:12667489 ]
Rao MS, Subbarao V, Yeldandi AV, Reddy JK: Hepatocarcinogenicity of dehydroepiandrosterone in the rat. Cancer Res. 1992 May 15;52(10):2977-9. [PubMed:1316232 ]
Saruc M, Yuceyar H, Ayhan S, Turkel N, Tuzcuoglu I, Can M: The association of dehydroepiandrosterone, obesity, waist-hip ratio and insulin resistance with fatty liver in postmenopausal women--a hyperinsulinemic euglycemic insulin clamp study. Hepatogastroenterology. 2003 May-Jun;50(51):771-4. [PubMed:12828082 ]
Bamberg E, Aichinger A, Mitteregger G: In vitro metabolism of dehydroepiandrosterone and testosterone by canine hair follicle cells. Vet Dermatol. 2004 Feb;15(1):19-24. [PubMed:14989701 ]
Gordon GB, Bush TL, Helzlsouer KJ, Miller SR, Comstock GW: Relationship of serum levels of dehydroepiandrosterone and dehydroepiandrosterone sulfate to the risk of developing postmenopausal breast cancer. Cancer Res. 1990 Jul 1;50(13):3859-62. [PubMed:2141293 ]
Weill-Engerer S, David JP, Sazdovitch V, Liere P, Schumacher M, Delacourte A, Baulieu EE, Akwa Y: In vitro metabolism of dehydroepiandrosterone (DHEA) to 7alpha-hydroxy-DHEA and Delta5-androstene-3beta,17beta-diol in specific regions of the aging brain from Alzheimer's and non-demented patients. Brain Res. 2003 Apr 18;969(1-2):117-25. [PubMed:12676372 ]
Finlay EM, Morton MS, Gaskell SJ: Identification and quantification of dehydroepiandrosterone sulphate in saliva. Steroids. 1982 Jan;39(1):63-71. [PubMed:6210977 ]
Uzieblo-Zyczkowska B, Sidlo E, Stelmaszuk T: [Dehydroepiandrosterone (DHEA)--slows down the aging process?]. Pol Merkur Lekarski. 2005 Dec;19(114):831-4. [PubMed:16521435 ]
Prost O, Nicollier M, Laurent R, Adessi GL: Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. Arch Dermatol Res. 1985;277(3):195-200. [PubMed:3160310 ]
Friess E, Schiffelholz T, Steckler T, Steiger A: Dehydroepiandrosterone--a neurosteroid. Eur J Clin Invest. 2000 Dec;30 Suppl 3:46-50. [PubMed:11281367 ]
Hakkinen A, Pakarinen A, Hannonen P, Kautiainen H, Nyman K, Kraemer WJ, Hakkinen K: Effects of prolonged combined strength and endurance training on physical fitness, body composition and serum hormones in women with rheumatoid arthritis and in healthy controls. Clin Exp Rheumatol. 2005 Jul-Aug;23(4):505-12. [PubMed:16095120 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
Kim SB, Hill M, Kwak YT, Hampl R, Jo DH, Morfin R: Neurosteroids: Cerebrospinal fluid levels for Alzheimer's disease and vascular dementia diagnostics. J Clin Endocrinol Metab. 2003 Nov;88(11):5199-206. [PubMed:14602750 ]
Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13. [PubMed:15650074 ]
Miller KK, Cai J, Ripp SL, Pierce WM Jr, Rushmore TH, Prough RA: Stereo- and regioselectivity account for the diversity of dehydroepiandrosterone (DHEA) metabolites produced by liver microsomal cytochromes P450. Drug Metab Dispos. 2004 Mar;32(3):305-13. [PubMed:14977864 ]
Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4. [PubMed:16487434 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Dehydroepiandrosterone (NP0000667)

MOL for NP0000667 (Dehydroepiandrosterone)

3D MOL for NP0000667 (Dehydroepiandrosterone)

3D SDF for NP0000667 (Dehydroepiandrosterone)

3D-SDF for NP0000667 (Dehydroepiandrosterone)

PDB for NP0000667 (Dehydroepiandrosterone)

3D PDB for NP0000667 (Dehydroepiandrosterone)

SMILES for NP0000667 (Dehydroepiandrosterone)

INCHI for NP0000667 (Dehydroepiandrosterone)

Structure for NP0000667 (Dehydroepiandrosterone)

3D Structure for NP0000667 (Dehydroepiandrosterone)