NP-MRD: Showing NP-Card for DHEA sulfate (NP0086693)

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Record Information

Version

2.0

Created at

2022-05-11 16:28:21 UTC

Updated at

2022-05-11 16:28:21 UTC

NP-MRD ID

NP0086693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

DHEA sulfate

Description

Dehydroepiandrosterone sulfate, also known as 17-ketoandrost-5-en-3b-yl sulfate or 3-O-sulfodehydroepiandrosterone, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. A steroid sulfate that is the 3-sulfooxy derivative of dehydroepiandrosterone. Dehydroepiandrosterone sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, dehydroepiandrosterone sulfate participates in a number of enzymatic reactions. In particular, adenosine 3',5'-diphosphate and dehydroepiandrosterone sulfate can be biosynthesized from phosphoadenosine phosphosulfate and dehydroepiandrosterone through its interaction with the enzyme sulfotransferase family cytosolic 2B member 1. In addition, dehydroepiandrosterone sulfate can be converted into dehydroepiandrosterone and sulfate through its interaction with the enzyme steryl-sulfatase. In humans, dehydroepiandrosterone sulfate is involved in androgen and estrogen metabolism. Dehydroepiandrosterone sulfate is a potentially toxic compound. DHEA sulfate is found in Apis cerana and Mus musculus. DHEA sulfate was first documented in 1981 (PMID: 6268694). Dehydroepiandrosterone sulfate, with regard to humans, has been found to be associated with several diseases such as aromatase deficiency, congenital adrenal hyperplasia, due to 17-hydroxylase-deficiency, hirsutism, and colorectal cancer; dehydroepiandrosterone sulfate has also been linked to the inborn metabolic disorder 11-beta-hydroxylase deficiency (PMID: 9933021) (PMID: 7664601) (PMID: 16837617).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306191804272D          

 28 31  0  0  0  0            999 V2000
10000.004110000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.144510001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1445 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8632 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1483 9998.5377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7344 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5600 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4291 9998.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.430310000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.7162 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2912 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5767 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5767 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2912 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.430810001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.716310000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7163 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4308 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.1453 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.145310000.6121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0029 9999.3661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0029 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7174 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4319 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9299 9999.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.414810000.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.930010000.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.185010001.6515    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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 13  4  1  1  0  0  0
 11 21  1  0  0  0  0
 14 22  1  0  0  0  0
 21  1  1  1  0  0  0
 20  2  1  1  0  0  0
 19  3  1  6  0  0  0
 17 21  1  0  0  0  0
 24 18  1  0  0  0  0
 18  9  1  1  0  0  0
 17 10  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 19 25  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -3.3897   -1.9068    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4405   -0.5131    0.3157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0863   -0.3645   -1.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301   -0.5497   -1.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157    0.1894   -0.4544 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1315   -0.0374    0.9859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2123    0.6606    1.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1868    0.2738    1.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6047   -0.0825    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0246   -0.4455    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733    0.4797   -0.8328 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8629    0.1218   -1.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0051    1.2334   -0.6444 S   0  0  2  0  0  6  0  0  0  0  0  0
    5.3560    2.3913    0.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8491    1.7006   -1.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0424    0.5018    0.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    0.6126   -2.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.9232   -1.7060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -0.1329   -0.7357 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8834   -1.5028   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5457    0.4463    1.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1556    0.4124    2.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6498    0.3902    2.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7606    0.0744    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6723    0.2359   -0.0904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4177   -2.3565    0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.0337    1.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9012   -2.5882    0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -1.1336   -1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    0.6215   -1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4313   -0.1524   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3517   -1.6417   -1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972    1.2854   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376   -1.1316    1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4474    0.2638    2.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443    1.7628    1.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8920    0.3053    2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6329   -0.2272    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1974   -1.5107    0.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6101    1.4991   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7239   -0.0447    0.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7398   -0.2602   -2.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975    1.4726   -2.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7080    0.9700   -2.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2536    1.9003   -1.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675   -2.2460   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3991   -1.5637   -2.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -1.7289   -1.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6214    1.4322    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8839    1.3378    3.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412   -0.4360    3.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0417    1.4324    2.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1835   -0.3402    2.7580 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
 24 25  2  0
 24  2  1  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 11 12  1  0
 13 12  1  6
 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 49  1  6
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  6 34  1  1
  7 35  1  0
  7 36  1  0
  8 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  1
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 16 41  1  0
M  END


  Mrv1652306191804272D          

 28 31  0  0  0  0            999 V2000
10000.004110000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.144510001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1445 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8632 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1483 9998.5377    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7344 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5600 9999.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4291 9998.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.430310000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.7162 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2912 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5767 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5767 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2912 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.430810001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.716310000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7163 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4308 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.1453 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.145310000.6121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.0029 9999.3661    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0029 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7174 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4319 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9299 9999.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.414810000.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.930010000.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.185010001.6515    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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 13  4  1  1  0  0  0
 11 21  1  0  0  0  0
 14 22  1  0  0  0  0
 21  1  1  1  0  0  0
 20  2  1  1  0  0  0
 19  3  1  6  0  0  0
 17 21  1  0  0  0  0
 24 18  1  0  0  0  0
 18  9  1  1  0  0  0
 17 10  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 19 25  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=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/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
CZWCKYRVOZZJNM-USOAJAOKSA-N

> <FORMULA>
C19H28O5S

> <MOLECULAR_WEIGHT>
368.488

> <EXACT_MASS>
368.165744696

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
39.8474725985752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
3.416690823333334

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.957705855662745

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3632754765266997

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4756492107864165

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
94.6507

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,5S,10R,11S,15S)-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                                 19-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-18         0                                  
HETATM    1  C   UNK     0    8666.6748667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.6708669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8670.6708664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8662.6788663.164   0.000  0.00  0.00           O+0
HETATM    5  S   UNK     0    8661.3438663.937   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0    8660.5718665.272   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8662.1128665.272   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8660.0018663.161   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0    8669.3378667.030   0.000  0.00  0.00           H+0
HETATM   10  H   UNK     0    8668.0048664.725   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0    8665.3448666.253   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0108665.483   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0108663.943   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.3448663.173   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3378668.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0048667.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.0048666.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3378665.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6718666.269   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.6718667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8666.6728665.483   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.6728663.943   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0068663.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.3408663.943   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8672.1368665.793   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8673.0418667.039   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8672.1368668.285   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8672.6128669.749   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   20                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   18                                                            
CONECT   10   17                                                            
CONECT   11   12   21                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14    4                                                  
CONECT   14   13   22                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21   10                                             
CONECT   18   17   19   24    9                                             
CONECT   19   18   20    3   25                                             
CONECT   20   15   19    2   27                                             
CONECT   21   22   11    1   17                                             
CONECT   22   21   23   14                                                  
CONECT   23   22   24                                                       
CONECT   24   23   18                                                       
CONECT   25   26   19                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(3-beta)-3-(Sulfooxy)androst-5-en-17-one	ChEBI
17-Ketoandrost-5-en-3beta-yl sulfate	ChEBI
17-Oxoandrost-5-en-3beta-yl hydrogen sulphate	ChEBI
3-O-Sulfodehydroepiandrosterone	ChEBI
3beta-Hydroxyandrost-5-en-17-one 3-sulfate	ChEBI
Androst-5-en-17-on-3beta-yl sulfuric acid	ChEBI
Dehydroepiandrosterone 3-sulfate	ChEBI
Dehydroepiandrosterone monosulfate	ChEBI
Dehydroepiandrosterone sulphate	ChEBI
Dehydroisoandrosterone sulfate	ChEBI
Dehydroisoandrosterone-3-sulfate	ChEBI
DHEA sulfate	ChEBI
DHEA-S	ChEBI
DHEAS	ChEBI
Prasterone sulfate	ChEBI
(3-b)-3-(Sulfooxy)androst-5-en-17-one	Generator
(3-b)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-beta)-3-(Sulphooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulfooxy)androst-5-en-17-one	Generator
(3-Β)-3-(sulphooxy)androst-5-en-17-one	Generator
17-Ketoandrost-5-en-3b-yl sulfate	Generator
17-Ketoandrost-5-en-3b-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3b-yl sulphate	Generator
17-Ketoandrost-5-en-3b-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3beta-yl sulphate	Generator
17-Ketoandrost-5-en-3beta-yl sulphuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulfate	Generator
17-Ketoandrost-5-en-3β-yl sulfuric acid	Generator
17-Ketoandrost-5-en-3β-yl sulphate	Generator
17-Ketoandrost-5-en-3β-yl sulphuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3b-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3beta-yl hydrogen sulphuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulfuric acid	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphate	Generator
17-Oxoandrost-5-en-3β-yl hydrogen sulphuric acid	Generator
3-O-Sulphodehydroepiandrosterone	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3b-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphate	Generator
3beta-Hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulfuric acid	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphate	Generator
3Β-hydroxyandrost-5-en-17-one 3-sulphuric acid	Generator
Androst-5-en-17-on-3b-yl sulfate	Generator
Androst-5-en-17-on-3b-yl sulfuric acid	Generator
Androst-5-en-17-on-3b-yl sulphate	Generator
Androst-5-en-17-on-3b-yl sulphuric acid	Generator
Androst-5-en-17-on-3beta-yl sulfate	Generator
Androst-5-en-17-on-3beta-yl sulphate	Generator
Androst-5-en-17-on-3beta-yl sulphuric acid	Generator
Androst-5-en-17-on-3β-yl sulfate	Generator
Androst-5-en-17-on-3β-yl sulfuric acid	Generator
Androst-5-en-17-on-3β-yl sulphate	Generator
Androst-5-en-17-on-3β-yl sulphuric acid	Generator
Dehydroepiandrosterone 3-sulfuric acid	Generator
Dehydroepiandrosterone 3-sulphate	Generator
Dehydroepiandrosterone 3-sulphuric acid	Generator
Dehydroepiandrosterone monosulfuric acid	Generator
Dehydroepiandrosterone monosulphate	Generator
Dehydroepiandrosterone monosulphuric acid	Generator
Dehydroepiandrosterone sulfuric acid	Generator
Dehydroepiandrosterone sulphuric acid	Generator
Dehydroisoandrosterone sulfuric acid	Generator
Dehydroisoandrosterone sulphate	Generator
Dehydroisoandrosterone sulphuric acid	Generator
Dehydroisoandrosterone-3-sulfuric acid	Generator
Dehydroisoandrosterone-3-sulphate	Generator
Dehydroisoandrosterone-3-sulphuric acid	Generator
DHEA sulfuric acid	Generator
DHEA sulphate	Generator
DHEA sulphuric acid	Generator
Prasterone sulfuric acid	Generator
Prasterone sulphate	Generator
Prasterone sulphuric acid	Generator
(3beta)-3-(Sulfooxy)-androst-5-en-17-one	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulfate	HMDB
17-Oxoandrost-5-en-3-yl hydrogen sulphate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-b-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulfate	HMDB
3-beta-Hydroxyandrost-5-en-17-one 3-sulphate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3b-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulfate	HMDB
3beta-Hydroxy-androst-5-en-17-one hydrogen sulphate	HMDB
Dehydroepiandrosterone-3-sulfate	HMDB
Dehydroepiandrosterone-3-sulphate	HMDB
Formylisoglutamic acid	HMDB
Prasterone-3-sulfate	HMDB
Prasterone-3-sulphate	HMDB
DHA sulfate	HMDB
Sulfate, dehydroisoandrosterone	HMDB
Sulfate, prasterone	HMDB
Sulfate, dhea	HMDB
Sulfate, dehydroepiandrosterone	HMDB
Sulfate, dha	HMDB

Chemical Formula

C₁₉H₂₈O₅S

Average Mass

368.4880 Da

Monoisotopic Mass

368.16574 Da

IUPAC Name

[(1S,2R,5S,10R,11S,15S)-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,15S)-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@@]12CCC(=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/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1

InChI Key

CZWCKYRVOZZJNM-USOAJAOKSA-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
Apis cerana	LOTUS Database	35616633
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
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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
17-oxosteroid
Oxosteroid
Delta-5-steroid
Sulfuric acid ester
Alkyl sulfate
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:16814 )
17-oxo steroid (CHEBI:16814 )
sulfates (C04555 )
C19 steroids (androgens) and derivatives (C04555 )
Androgens (C04555 )
Sulfates (LMST05020010 )

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	0.49	ALOGPS
logP	3.42	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.65 m³·mol⁻¹	ChemAxon
Polarizability	39.85 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

HMDB0001032

DrugBank ID

DB05804

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022381

KNApSAcK ID

Not Available

Chemspider ID

12074

KEGG Compound ID

C04555

BioCyc ID

DEHYDRO-EPIANDROSTERONE-SULFATE

BiGG ID

44038

Wikipedia Link

Dehydroepiandrosterone_sulfate

METLIN ID

4095

PubChem Compound

12594

PDB ID

Not Available

ChEBI ID

16814

Good Scents ID

Not Available

References

General References

Roberts E: The importance of being dehydroepiandrosterone sulfate (in the blood of primates): a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;57(4):329-46. [PubMed:9933021 ]
Gu H, Li Y, Rong L: [The effect of sodium prasterone sulfate on lactation]. Zhonghua Fu Chan Ke Za Zhi. 1995 Apr;30(4):197-9. [PubMed:7664601 ]
Dalla Valle L, Toffolo V, Nardi A, Fiore C, Bernante P, Di Liddo R, Parnigotto PP, Colombo L: Tissue-specific transcriptional initiation and activity of steroid sulfatase complementing dehydroepiandrosterone sulfate uptake and intracrine steroid activations in human adipose tissue. J Endocrinol. 2006 Jul;190(1):129-39. doi: 10.1677/joe.1.06811. [PubMed:16837617 ]
Zappulla F, Ventura D, Capelli M, Cassio A, Balsamo A, Frejaville E, Bolelli G, Cacciari E: Gonadal and adrenal secretion of dehydroepiandrosterone sulfate in prepubertal and pubertal subjects. J Endocrinol Invest. 1981 Apr-Jun;4(2):197-202. doi: 10.1007/BF03350452. [PubMed:6268694 ]

Showing NP-Card for DHEA sulfate (NP0086693)

MOL for NP0086693 (DHEA sulfate)

3D MOL for NP0086693 (DHEA sulfate)

3D SDF for NP0086693 (DHEA sulfate)

3D-SDF for NP0086693 (DHEA sulfate)

PDB for NP0086693 (DHEA sulfate)

3D PDB for NP0086693 (DHEA sulfate)

SMILES for NP0086693 (DHEA sulfate)

INCHI for NP0086693 (DHEA sulfate)

Structure for NP0086693 (DHEA sulfate)

3D Structure for NP0086693 (DHEA sulfate)