NP-MRD: Showing NP-Card for 16alpha-hydroxydehydroepiandrosterone 3-sulfate (NP0092614)

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Record Information

Version

2.0

Created at

2022-05-11 19:11:10 UTC

Updated at

2022-05-11 19:11:10 UTC

NP-MRD ID

NP0092614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16alpha-hydroxydehydroepiandrosterone 3-sulfate

Description

16Alpha-hydroxydehydroepiandrosterone 3-sulfate, also known as 16a-hydroxy-dhea 3-sulfuric acid or (3beta)-16alpha-hydroxy-17-oxoandrost-5-en-3-yl sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. 16alpha-hydroxydehydroepiandrosterone 3-sulfate was first documented in 1978 (PMID: 153014). 16Alpha-hydroxydehydroepiandrosterone 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303102017002D          

 29 32  0  0  0  0            999 V2000
 9999.636810000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.775610001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7756 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4960 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7810 9998.5377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3671 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1928 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0619 9998.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.063510000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3493 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3499 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0644 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.063010001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.348510000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3485 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0630 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9234 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2089 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2089 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9234 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6379 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6379 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.047110000.1996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.562110000.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.777510000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7775 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.5621 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.817010001.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.872110000.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  6  0  0  0
 19  4  1  1  0  0  0
 22  1  1  1  0  0  0
 21 11  2  0  0  0  0
 15 10  1  6  0  0  0
 15 22  1  0  0  0  0
 12 16  1  0  0  0  0
 16  9  1  1  0  0  0
 16 26  1  0  0  0  0
 26  3  1  6  0  0  0
 13 25  1  0  0  0  0
 25  2  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -3.3986    1.9796    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842    0.5103    0.6713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5347    0.2041    1.9441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    0.6922    1.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856   -0.1375    0.5910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2398    0.1875   -0.6808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6323   -0.4093   -1.8975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8308   -0.1574   -1.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.0017   -0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0387    0.2503   -0.8897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8194   -0.6337    0.0410 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9510    0.0918    0.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3714   -0.5989   -0.0845 S   0  0  1  0  0  6  0  0  0  0  0  0
    6.9303   -1.4177    1.0454 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1559   -1.5295   -1.2405 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4597    0.6167   -0.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1230   -1.0841    1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -1.2999    1.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9777   -0.0632    0.5175 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4827    1.1104    1.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417   -0.2723   -0.4250 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6052   -0.1632   -1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9373   -0.3081   -0.8200 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3037   -1.6720   -0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6607   -0.0578    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3654   -0.2584    1.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9256    2.3137   -0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735    2.3223    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851    2.5581    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9660    0.7525    2.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830   -0.8780    2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.7490    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    0.6474    2.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683   -1.2050    0.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1734    1.3049   -0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -1.4812   -2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    0.1234   -2.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3305   -0.0995   -2.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2678    1.3315   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3456    0.0393   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -1.5241   -0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088    1.5129   -0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.4084    2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -2.0619    1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2269   -1.4469    2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4548   -2.2021    0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5741    1.2745    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4333    0.7831    2.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8865    1.9968    1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5871   -1.3302   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -0.9793   -2.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705    0.7982   -2.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7160    0.3437   -1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0989   -1.8162   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25  2  1  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 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 11 12  1  0
 13 12  1  1
 13 16  1  0
 13 14  2  0
 13 15  2  0
  2 21  1  0
 19  5  1  0
  6 21  1  0
 19  9  1  0
 21 50  1  1
 22 51  1  0
 22 52  1  0
 23 53  1  6
 24 54  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  1
  6 35  1  6
  7 36  1  0
  7 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  6
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 16 42  1  0
M  END


  Mrv1652303102017002D          

 29 32  0  0  0  0            999 V2000
 9999.636810000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.775610001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7756 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4960 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7810 9998.5377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9996.3671 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1928 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0619 9998.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.063510000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3493 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.3499 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0644 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.063010001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.348510000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3485 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.0630 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9234 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2089 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2089 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9234 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6379 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6379 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.047110000.1996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.562110000.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.777510000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7775 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.5621 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.817010001.6516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.872110000.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  6  0  0  0
 19  4  1  1  0  0  0
 22  1  1  1  0  0  0
 21 11  2  0  0  0  0
 15 10  1  6  0  0  0
 15 22  1  0  0  0  0
 12 16  1  0  0  0  0
 16  9  1  1  0  0  0
 16 26  1  0  0  0  0
 26  3  1  6  0  0  0
 13 25  1  0  0  0  0
 25  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0092614

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O6S/c1-18-7-5-12(25-26(22,23)24)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)21/h3,12-16,20H,4-10H2,1-2H3,(H,22,23,24)/t12-,13+,14-,15-,16+,18-,19-/m0/s1

> <INCHI_KEY>
ALBNSVAJDFJRKQ-DNKQKWOHSA-N

> <FORMULA>
C19H28O6S

> <MOLECULAR_WEIGHT>
384.49

> <EXACT_MASS>
384.160659796

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.692100407087594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.12

> <JCHEM_LOGP>
2.545624902666667

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.382196791349624

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3632757272512883

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5064184958879894

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
96.14289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.9898667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.9818669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.9818664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.9938663.164   0.000  0.00  0.00           O+0
HETATM    5  S   UNK     0    8660.6588663.937   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0    8659.8858665.272   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.4278665.272   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8659.3168663.161   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0    8668.6528667.030   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8667.3198664.725   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0    8667.3208663.173   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.6548663.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.6518668.579   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3178667.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3178666.269   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6518665.499   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6578666.253   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3238665.483   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.3238663.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6578663.173   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9918663.943   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8665.9918665.483   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8672.3558667.039   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.4498668.285   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8669.9858667.809   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8669.9858666.269   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8671.4498665.793   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8671.9258669.750   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0    8673.8958667.039   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4    5   19                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   16                                                            
CONECT   10   15                                                            
CONECT   11   12   21                                                       
CONECT   12   11   16                                                       
CONECT   13   14   25                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   10   22                                             
CONECT   16   15   12    9   26                                             
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    4                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   11                                                  
CONECT   22   17   21    1   15                                             
CONECT   23   24   27   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   13    2                                             
CONECT   26   25   27   16    3                                             
CONECT   27   23   26                                                       
CONECT   28   24                                                            
CONECT   29   23                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
16a-Hydroxydehydroepiandrosterone 3-sulfate	Generator
16a-Hydroxydehydroepiandrosterone 3-sulfuric acid	Generator
16a-Hydroxydehydroepiandrosterone 3-sulphate	Generator
16a-Hydroxydehydroepiandrosterone 3-sulphuric acid	Generator
16alpha-Hydroxydehydroepiandrosterone 3-sulfuric acid	Generator
16alpha-Hydroxydehydroepiandrosterone 3-sulphate	Generator
16alpha-Hydroxydehydroepiandrosterone 3-sulphuric acid	Generator
16α-Hydroxydehydroepiandrosterone 3-sulfate	Generator
16α-hydroxydehydroepiandrosterone 3-sulfuric acid	Generator
16α-Hydroxydehydroepiandrosterone 3-sulphate	Generator
16α-hydroxydehydroepiandrosterone 3-sulphuric acid	Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3b)-16a-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3b,16a)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, ChEBI
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3beta)-16alpha-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, ChEBI
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3beta,16alpha)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
(3β)-16α-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, Generator
(3β)-16α-hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3β)-16α-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3β)-16α-hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
(3β,16α)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulfate	HMDB, Generator
(3β,16α)-16-hydroxy-17-oxoandrost-5-en-3-yl sulfuric acid	HMDB, Generator
(3β,16α)-16-Hydroxy-17-oxoandrost-5-en-3-yl sulphate	HMDB, Generator
(3β,16α)-16-hydroxy-17-oxoandrost-5-en-3-yl sulphuric acid	HMDB, Generator
16a-Hydroxy-DHEA 3-sulfate	HMDB, Generator
16a-Hydroxy-DHEA 3-sulfuric acid	HMDB, Generator
16a-Hydroxy-DHEA 3-sulphate	HMDB, Generator
16a-Hydroxy-DHEA 3-sulphuric acid	HMDB, Generator
16alpha-Hydroxy-DHEA 3-sulfate	HMDB, ChEBI
16alpha-Hydroxy-DHEA 3-sulfuric acid	HMDB, Generator
16alpha-Hydroxy-DHEA 3-sulphate	HMDB, Generator
16alpha-Hydroxy-DHEA 3-sulphuric acid	HMDB, Generator
16α-Hydroxy-DHEA 3-sulfate	HMDB, Generator
16α-hydroxy-DHEA 3-sulfuric acid	HMDB, Generator
16α-Hydroxy-DHEA 3-sulphate	HMDB, Generator
16α-hydroxy-DHEA 3-sulphuric acid	HMDB, Generator
3b-Sulfooxy-16a-hydroxyandrost-5-en-17-one	HMDB, Generator
3b-Sulphooxy-16a-hydroxyandrost-5-en-17-one	HMDB, Generator
3beta-Sulfooxy-16alpha-hydroxyandrost-5-en-17-one	HMDB, ChEBI
3beta-Sulphooxy-16alpha-hydroxyandrost-5-en-17-one	HMDB, Generator
3β-Sulfooxy-16α-hydroxyandrost-5-en-17-one	HMDB, Generator
3β-sulphooxy-16α-hydroxyandrost-5-en-17-one	HMDB, Generator
(3beta,16alpha)-16-Hydroxy-3-(sulfooxy)androst-5-en-17-one	HMDB
(3β,16α)-16-Hydroxy-3-(sulfooxy)androst-5-en-17-one	HMDB
16alpha-Hydroxy DHEA 3-sulfate	HMDB
16alpha-Hydroxy DHEA 3-sulphate	HMDB
16alpha-Hydroxy DHEA sulfate	HMDB
16alpha-Hydroxy DHEA sulphate	HMDB
16alpha-Hydroxy-DHEA sulfate	HMDB
16alpha-Hydroxy-DHEA sulphate	HMDB
16alpha-Hydroxydehydroepiandrosterone 3-sulfate	HMDB
16alpha-Hydroxydehydroisoandrosterone sulfate	HMDB
16alpha-Hydroxydehydroisoandrosterone sulphate	HMDB
16alpha-OH DHEAS	HMDB
16alpha-OH-DHEA-3S	HMDB
16alpha-OH-DHEA-S	HMDB
16alpha-OH-DHEAS	HMDB
16α-Hydroxy DHEA 3-sulfate	HMDB
16α-Hydroxy DHEA 3-sulphate	HMDB
16α-Hydroxy DHEA sulfate	HMDB
16α-Hydroxy DHEA sulphate	HMDB
16α-Hydroxy-DHEA sulfate	HMDB
16α-Hydroxy-DHEA sulphate	HMDB
16α-Hydroxydehydroisoandrosterone sulfate	HMDB
16α-Hydroxydehydroisoandrosterone sulphate	HMDB
16α-OH DHEAS	HMDB
16α-OH-DHEA-3S	HMDB
16α-OH-DHEA-S	HMDB
16α-OH-DHEAS	HMDB
3beta,16alpha-Dihydroxy-5-androsten-17-one 3-sulfate	HMDB
3beta,16alpha-Dihydroxy-5-androsten-17-one 3-sulphate	HMDB
3β,16α-Dihydroxy-5-androsten-17-one 3-sulfate	HMDB
3β,16α-Dihydroxy-5-androsten-17-one 3-sulphate	HMDB
(3beta,16alpha)-3,16-Dihydroxyandrost-5-en-17-one sulfate	HMDB
(3beta,16alpha)-3,16-Dihydroxyandrost-5-en-17-one sulphate	HMDB
(3β,16α)-3,16-Dihydroxyandrost-5-en-17-one sulfate	HMDB
(3β,16α)-3,16-Dihydroxyandrost-5-en-17-one sulphate	HMDB
3b,16a-Dihydroxyandrostenone sulfate	HMDB
3b,16a-Dihydroxyandrostenone sulphate	HMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-one sulfate	HMDB
3beta,16alpha-Dihydroxyandrost-5-en-17-one sulphate	HMDB
3beta,16alpha-Dihydroxyandrostenone sulfate	HMDB
3beta,16alpha-Dihydroxyandrostenone sulphate	HMDB
3β,16α-Dihydroxyandrost-5-en-17-one sulfate	HMDB
3β,16α-Dihydroxyandrost-5-en-17-one sulphate	HMDB
3β,16α-Dihydroxyandrostenone sulfate	HMDB
3β,16α-Dihydroxyandrostenone sulphate	HMDB

Chemical Formula

C₁₉H₂₈O₆S

Average Mass

384.4900 Da

Monoisotopic Mass

384.16066 Da

IUPAC Name

[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,2R,5S,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H28O6S/c1-18-7-5-12(25-26(22,23)24)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(20)17(19)21/h3,12-16,20H,4-10H2,1-2H3,(H,22,23,24)/t12-,13+,14-,15-,16+,18-,19-/m0/s1

InChI Key

ALBNSVAJDFJRKQ-DNKQKWOHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
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, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 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
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Androstane-skeleton
Hydroxysteroid
17-oxosteroid
Oxosteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
Delta-5-steroid
Sulfate-ester
Sulfuric acid monoester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Sulfates (LMST05020022 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.12	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.14 m³·mol⁻¹	ChemAxon
Polarizability	40.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062611

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB034847

KNApSAcK ID

Not Available

Chemspider ID

24850136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20848951

PDB ID

Not Available

ChEBI ID

87774

Good Scents ID

Not Available

References

General References

Numazawa M, Osawa Y: Improved synthesis of 16alpha-hydroxylated androgens: intermediates of estriol formation in pregnancy. Steroids. 1978 Nov;32(4):519-27. doi: 10.1016/0039-128x(78)90063-6. [PubMed:153014 ]

Showing NP-Card for 16alpha-hydroxydehydroepiandrosterone 3-sulfate (NP0092614)

MOL for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

3D MOL for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

3D SDF for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

3D-SDF for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

PDB for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

3D PDB for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

SMILES for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

INCHI for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

Structure for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)

3D Structure for NP0092614 (16alpha-hydroxydehydroepiandrosterone 3-sulfate)