Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 22:15:19 UTC

Update Date

2022-03-07 02:49:21 UTC

HMDB ID

HMDB0004611

Secondary Accession Numbers

HMDB04611

Metabolite Identification

Common Name

7a-Hydroxydehydroepiandrosterone

Description

7a-Hydroxydehydroepiandrosterone is a major metabolite of dehydroepiandrosterone (DHEA), which is is 7alpha-hydroxylated by the cytochrome P450 7B1 (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase, CYP7B1) in the human brain and liver microsomes. Exposure to the proinflammatory cytokines TNFalpha, IL-1alpha, IL-1beta, and IL-17 increases CYP7B activity in synovial tissue. Increased CYP7B activity leads to higher levels of the DHEA metabolite 7alpha-OH-DHEA in synovial fluid, which may contribute to the maintenance of the chronic inflammation observed in rheumatoid arthritis patients. The glucocorticoid dhydrocorticosterone inhibits the conversion of DHEA to 7a-Hydroxydehydroepiandrosterone. The total levels of 7a-Hydroxydehydroepiandrosterone are increased in serum of patients with Alzheimer's disease. (PMID: 17467270 , 15751070 , 12667489 , 9520908 ).

Structure

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


  Mrv0541 02231219572D          

 25 28  0  0  1  0            999 V2000
   27.5656  -20.7838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5844  -17.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0987  -20.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1188  -19.1080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.8331  -19.5204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.5476  -19.1080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.5476  -18.2830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.3681  -19.5261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.1188  -18.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8331  -17.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8464  -20.3795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.3281  -19.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3614  -20.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6035  -19.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3281  -18.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8095  -18.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1056  -20.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5476  -17.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3745  -18.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5898  -20.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8216  -19.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8147  -20.3912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.6903  -18.7780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.3397  -19.9587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.7752  -19.7642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  2 15  2  0  0  0  0
 22  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 23  1  6  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  5 24  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  7 15  1  0  0  0  0
  7 18  1  1  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 17  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
M  END

HMDB0004611
     RDKit          3D
7a-Hydroxydehydroepiandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8294   -0.3354    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -0.6112   -0.1479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0240   -1.8455   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.7254    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -0.5646   -0.3862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6732    0.7346   -0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0434    1.6270   -1.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2077    1.0278   -2.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103    1.6053   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.7179   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.8065   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -0.1073    0.6553 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3153    0.5408    1.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.4498    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427   -1.6023    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3538    0.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2686    0.0975    1.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    0.5493   -0.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0171    1.6517   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.4828   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8561   -1.3755   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.3066    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    0.0495    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    0.4243    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8303   -1.8260   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -2.7894   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -2.6494   -0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8079   -1.6511    1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -0.7880   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    1.2830    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3871    2.6310   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.8657   -3.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    2.3675   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392    1.8629   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587    0.7107   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -0.2582    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    1.5213    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488   -2.2576    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581   -1.7069    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.4042    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.8902   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549   -0.5976    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.1478    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    0.0772    2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.3428   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    2.5478   -1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656    1.9224    0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0801    1.2161    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.2719   -1.7820 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 18  2  1  0
 21  2  1  0
 16  5  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  6
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END


  Mrv0541 02231219572D          

 25 28  0  0  1  0            999 V2000
   27.5656  -20.7838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5844  -17.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0987  -20.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1188  -19.1080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.8331  -19.5204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.5476  -19.1080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.5476  -18.2830    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.3681  -19.5261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.1188  -18.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8331  -17.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8464  -20.3795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.3281  -19.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3614  -20.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6035  -19.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3281  -18.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8095  -18.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1056  -20.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5476  -17.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3745  -18.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5898  -20.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8216  -19.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8147  -20.3912    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.6903  -18.7780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.3397  -19.9587    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.7752  -19.7642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  6  0  0  0
  2 15  2  0  0  0  0
 22  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 23  1  6  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  5 24  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 25  1  6  0  0  0
  7 10  1  0  0  0  0
  7 15  1  0  0  0  0
  7 18  1  1  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  8 19  1  1  0  0  0
  9 10  1  0  0  0  0
 11 17  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 13 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004611

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1

> <INCHI_KEY>
OLPSAOWBSPXZEA-JIEICEMKSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.4238

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.77649648584605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
2.2088477183333333

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.25349888537043

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.20423342151809

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8087658381000774

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
86.0974

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7β-oh-dhea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004611
     RDKit          3D
7a-Hydroxydehydroepiandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8294   -0.3354    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -0.6112   -0.1479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0240   -1.8455   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.7254    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -0.5646   -0.3862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6732    0.7346   -0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0434    1.6270   -1.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2077    1.0278   -2.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103    1.6053   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.7179   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.8065   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -0.1073    0.6553 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3153    0.5408    1.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.4498    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427   -1.6023    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3538    0.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2686    0.0975    1.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    0.5493   -0.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0171    1.6517   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.4828   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8561   -1.3755   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.3066    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    0.0495    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    0.4243    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8303   -1.8260   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -2.7894   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -2.6494   -0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8079   -1.6511    1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -0.7880   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    1.2830    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3871    2.6310   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.8657   -3.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    2.3675   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392    1.8629   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587    0.7107   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -0.2582    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    1.5213    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488   -2.2576    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581   -1.7069    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.4042    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.8902   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549   -0.5976    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.1478    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    0.0772    2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.3428   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    2.5478   -1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656    1.9224    0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0801    1.2161    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.2719   -1.7820 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 18  2  1  0
 21  2  1  0
 16  5  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  6
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      51.456 -38.796   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      53.358 -32.196   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      43.118 -38.828   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      48.755 -35.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      50.088 -36.438   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      51.422 -35.668   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      51.422 -34.128   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.354 -36.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.755 -34.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      50.088 -33.358   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.113 -38.042   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      52.879 -36.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.341 -38.053   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      45.927 -35.580   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      52.879 -33.659   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      53.778 -34.898   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      48.730 -38.855   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      51.422 -32.588   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      47.366 -34.909   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.901 -38.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      44.467 -36.393   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.454 -38.064   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      49.822 -35.052   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      51.034 -37.256   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      51.847 -36.893   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   15                                                            
CONECT    3   22                                                            
CONECT    4    5    8    9   23                                             
CONECT    5    4    6   11   24                                             
CONECT    6    5    7   12   25                                             
CONECT    7    6   10   15   18                                             
CONECT    8    4   13   14   19                                             
CONECT    9    4   10                                                       
CONECT   10    7    9                                                       
CONECT   11    1    5   17                                                  
CONECT   12    6   16                                                       
CONECT   13    8   17   20                                                  
CONECT   14    8   21                                                       
CONECT   15    2    7   16                                                  
CONECT   16   12   15                                                       
CONECT   17   11   13                                                       
CONECT   18    7                                                            
CONECT   19    8                                                            
CONECT   20   13   22                                                       
CONECT   21   14   22                                                       
CONECT   22    3   20   21                                                  
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0004611
HETATM    1  C1  UNL     1      -2.829  -0.335   1.337  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.771  -0.611  -0.148  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.024  -1.845  -0.489  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.659  -1.725   0.159  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.089  -0.565  -0.386  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.673   0.735  -0.383  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.043   1.627  -1.409  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.208   1.028  -2.661  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.510   1.605  -1.212  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.137   0.718  -0.445  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.596   0.807  -0.335  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.214  -0.107   0.655  1.00  0.00           C  
HETATM   13  O2  UNL     1       4.315   0.541   1.909  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.599  -1.450   0.777  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.243  -1.602   0.200  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.398  -0.354   0.298  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.269   0.097   1.718  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.062   0.549  -0.868  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.017   1.652  -0.579  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.379   0.978  -0.809  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.109  -0.483  -0.722  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.856  -1.376  -1.061  1.00  0.00           O  
HETATM   23  H1  UNL     1      -2.724  -1.307   1.867  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.834   0.049   1.616  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.104   0.424   1.656  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.830  -1.826  -1.599  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.529  -2.789  -0.230  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.106  -2.649  -0.110  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.808  -1.651   1.260  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.317  -0.788  -1.466  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.610   1.283   0.569  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.387   2.631  -1.439  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.617   0.866  -3.165  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.081   2.368  -1.734  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.839   1.863  -0.017  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.059   0.711  -1.346  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.291  -0.258   0.344  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.183   1.521   1.788  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.249  -2.258   0.338  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.558  -1.707   1.874  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.710  -2.404   0.787  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.314  -1.890  -0.854  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.855  -0.598   2.367  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.633   1.148   1.881  1.00  0.00           H  
HETATM   45  H23 UNL     1       0.234   0.077   2.065  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.094   0.343  -1.958  1.00  0.00           H  
HETATM   47  H25 UNL     1      -2.897   2.548  -1.191  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.966   1.922   0.510  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.080   1.216   0.029  1.00  0.00           H  
HETATM   50  H28 UNL     1      -4.798   1.272  -1.782  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   18   21
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   16   30
CONECT    6    7   18   31
CONECT    7    8    9   32
CONECT    8   33
CONECT    9   10   10   34
CONECT   10   11   16
CONECT   11   12   35   36
CONECT   12   13   14   37
CONECT   13   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17
CONECT   17   43   44   45
CONECT   18   19   46
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22   22
END

HMDB0004611
     RDKit          3D
7a-Hydroxydehydroepiandrosterone
 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.8294   -0.3354    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710   -0.6112   -0.1479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0240   -1.8455   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -1.7254    0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0894   -0.5646   -0.3862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6732    0.7346   -0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0434    1.6270   -1.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2077    1.0278   -2.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103    1.6053   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373    0.7179   -0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5956    0.8065   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -0.1073    0.6553 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3153    0.5408    1.9085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.4498    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427   -1.6023    0.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -0.3538    0.2975 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2686    0.0975    1.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    0.5493   -0.8679 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0171    1.6517   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3788    0.9783   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -0.4828   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8561   -1.3755   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7235   -1.3066    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    0.0495    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    0.4243    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8303   -1.8260   -1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5288   -2.7894   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -2.6494   -0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8079   -1.6511    1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3168   -0.7880   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102    1.2830    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3871    2.6310   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.8657   -3.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0812    2.3675   -1.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392    1.8629   -0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587    0.7107   -1.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -0.2582    0.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835    1.5213    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2488   -2.2576    0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5581   -1.7069    1.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -2.4042    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.8902   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549   -0.5976    2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.1478    1.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    0.0772    2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.3428   -1.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    2.5478   -1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656    1.9224    0.5100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0801    1.2161    0.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7977    1.2719   -1.7820 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
  6 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 18  2  1  0
 21  2  1  0
 16  5  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  6
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,7alpha)-3,7-Dihydroxyandrost-5-en-17-one	ChEBI
3beta,7alpha-Dihydroxy-5-androstene-17-one	ChEBI
3beta,7alpha-Dihydroxyandrost-5-en-17-one	ChEBI
7alpha-Hydroxy-dhea	ChEBI
7alpha-OH-DHEA	ChEBI
(3b,7a)-3,7-Dihydroxyandrost-5-en-17-one	Generator
(3Β,7α)-3,7-dihydroxyandrost-5-en-17-one	Generator
3b,7a-Dihydroxy-5-androstene-17-one	Generator
3Β,7α-dihydroxy-5-androstene-17-one	Generator
3b,7a-Dihydroxyandrost-5-en-17-one	Generator
3Β,7α-dihydroxyandrost-5-en-17-one	Generator
7a-Hydroxy-dhea	Generator
7Α-hydroxy-dhea	Generator
7a-OH-DHEA	Generator
7Α-OH-dhea	Generator
7-Hydroxydehydroepiandrosterone	MeSH
7beta-Hydroxydehydroepiandrosterone	MeSH
7-Hydroxydehydroepiandrosterone, (3beta)-isomer	MeSH
7beta-OH-DHEA	MeSH
7 alpha-Hydroxydehydroepiandrosterone	MeSH
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomer	MeSH
(-)-7a-Hydroxydehydroepiandrosterone	HMDB
(3b,7a)-3,7-Dihydroxy-androst-5-en-17-one	HMDB
3b,7a-Dihydroxy-5-androsten-17-one	HMDB
3b,7a-Dihydroxy-androst-5-en-17-one	HMDB
7-a-OH-DHEA	HMDB
7-alpha-OH-DHEA	HMDB
7a-Hydroxydehydroisoandrosterone	HMDB

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.4238

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

(1S,2R,5S,9S,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

Traditional Name

7β-oh-dhea

CAS Registry Number

53-00-9

SMILES

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

InChI Identifier

InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15+,17-,18-,19-/m0/s1

InChI Key

OLPSAOWBSPXZEA-JIEICEMKSA-N

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
7-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
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:81471 )
C19 steroids (androgens) and derivatives (LMST02020101 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004611)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004611)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004611)

Source

Endogenous

Endogenous (HMDB: HMDB0004611)

Animal

Animal (HMDB: HMDB0004611)

Exogenous

Food

Food (HMDB: HMDB0004611)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0004611)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004611)

Molecular messenger

Hormone (HMDB: HMDB0004611)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004611)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 183 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.84	ALOGPS
logP	2.21	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.1 m³·mol⁻¹	ChemAxon
Polarizability	34.78 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.631	31661259
DarkChem	[M-H]-	166.205	31661259
DeepCCS	[M-2H]-	206.334	30932474
DeepCCS	[M+Na]+	181.133	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.07 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9027 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2365.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	464.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	494.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	985.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	409.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1294.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	340.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	41.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxydehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	2704.9	Standard polar	33892256
7a-Hydroxydehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	2693.3	Standard non polar	33892256
7a-Hydroxydehydroepiandrosterone	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C=C2C[C@@H](O)CC[C@]12C	2823.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7a-Hydroxydehydroepiandrosterone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CCC2=O	2735.6	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O	2723.8	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2702.2	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O	2689.5	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2731.3	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H]([C@H](O)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2717.5	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2673.4	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2714.7	Standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H]([C@H](O[Si](C)(C)C)C=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2967.2	Standard polar	33892256
7a-Hydroxydehydroepiandrosterone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12	2993.6	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@@H](O)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C1	2993.5	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2998.8	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C1	3211.5	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3295.9	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3252.4	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3397.4	Semi standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3107.1	Standard non polar	33892256
7a-Hydroxydehydroepiandrosterone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3[C@H](O[Si](C)(C)C(C)(C)C)C=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3265.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g0-0390000000-5b84fc74cc8c3d885c1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone GC-MS (2 TMS) - 70eV, Positive	splash10-003r-5204900000-bdb069dd8202b45f9ea3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7a-Hydroxydehydroepiandrosterone 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 - 7a-Hydroxydehydroepiandrosterone 10V, Positive-QTOF	splash10-00kr-0092000000-003d307a3c381597e38b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Positive-QTOF	splash10-0ap0-0190000000-7563041720b768705389	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Positive-QTOF	splash10-0a6u-3190000000-8012f9fad41969d73d46	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Negative-QTOF	splash10-0udi-0049000000-3459db2d82d83321802f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Negative-QTOF	splash10-0udr-0098000000-6a1aaf578c3c1719798a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Negative-QTOF	splash10-059f-2090000000-85d4a8001358a115f59b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Negative-QTOF	splash10-0udi-0009000000-93986d59045cc7fce551	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Negative-QTOF	splash10-0udi-0019000000-8b3060136e49afe5a336	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Negative-QTOF	splash10-0uy0-0093000000-e42b11a1c3c059294db3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 10V, Positive-QTOF	splash10-0a4i-0069000000-61a09d88b13611d21a89	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 20V, Positive-QTOF	splash10-0670-1981000000-b0f1410f207bdaec9fa1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7a-Hydroxydehydroepiandrosterone 40V, Positive-QTOF	splash10-05dl-3910000000-4b2efd9d887548375fc0	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB023382

KNApSAcK ID

Not Available

Chemspider ID

58963

KEGG Compound ID

C18045

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

7alpha-Hydroxy-DHEA

METLIN ID

Not Available

PubChem Compound

65517

PDB ID

Not Available

ChEBI ID

712194

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ishidate, Morizo; Okada, Masashi. Steroids. (1963), 2 pp. JP 38023170 19631031 Showa. CAN 60:12972 AN 1964:12972

Material Safety Data Sheet (MSDS)

Not Available

General References

Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]
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 ]
Dulos J, van der Vleuten MA, Kavelaars A, Heijnen CJ, Boots AM: CYP7B expression and activity in fibroblast-like synoviocytes from patients with rheumatoid arthritis: regulation by proinflammatory cytokines. Arthritis Rheum. 2005 Mar;52(3):770-8. [PubMed:15751070 ]
Attal-Khemis S, Dalmeyda V, Michot JL, Roudier M, Morfin R: Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease. J Gerontol A Biol Sci Med Sci. 1998 Mar;53(2):B125-32. [PubMed:9520908 ]

Enzymes

Enzyme Details

1. Cholesterol 7-alpha-monooxygenase

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:: CYP7A1
Uniprot ID:: P22680
Molecular weight:: 57660.155

Reactions

Dehydroepiandrosterone + Oxygen + NADPH + Hydrogen Ion → 7a-Hydroxydehydroepiandrosterone + NADP + Water	details

Enzyme Details

2. Corticosteroid 11-beta-dehydrogenase isozyme 1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:: HSD11B1
Uniprot ID:: P28845
Molecular weight:: 32400.665

References

Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]

Enzyme Details

3. 25-hydroxycholesterol 7-alpha-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP7B1
Uniprot ID:: O75881
Molecular weight:: 58255.325

References

Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24. [PubMed:17467270 ]

Showing metabocard for 7a-Hydroxydehydroepiandrosterone (HMDB0004611)

MOL for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

3D MOL for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

3D SDF for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

3D-SDF for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

PDB for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

3D PDB for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

SMILES for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

INCHI for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

Structure for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

3D Structure for HMDB0004611 (7a-Hydroxydehydroepiandrosterone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

References

References