NP-MRD: Showing NP-Card for Cortisol 21-sulfate (NP0092619)

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Record Information

Version

2.0

Created at

2022-05-11 19:11:18 UTC

Updated at

2022-05-11 19:11:18 UTC

NP-MRD ID

NP0092619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cortisol 21-sulfate

Description

Cortisol 21-sulfate, also known as SS441 compound or F(K)S CPD, 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 obtained by the formal condensation of hydroxy group at position 21 of cortisol with sulfuric acid. Cortisol 21-sulfate was first documented in 1964 (PMID: 5857563). Cortisol 21-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 2152866) (PMID: 24392764) (PMID: 5012753) (PMID: 8650705).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652303102017002D          

 34 37  0  0  1  0            999 V2000
    3.1508    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7280    1.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996    1.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799    1.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4754   -0.0044    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0072   -0.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061    0.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8447   -0.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8993    2.2548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0584   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  2  0  0  0  0
  5 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    1.6878   -0.2565    1.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2320   -0.0357    0.0455 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5737    1.2927   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7982    1.3356    0.4354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5963    1.4028    1.7916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6586    0.2075   -0.0459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9703   -1.1027    0.3181 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8125   -2.2767   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2548    0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7450   -1.0239    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -1.1336    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8015    0.0699    0.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8137    0.4889    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1328    0.7407   -1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973    1.2076   -0.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181    0.2708    0.3150 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2815    0.9899    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2720   -1.0948   -0.4813 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1072   -2.3076   -0.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3348   -1.7702   -1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771   -0.2941   -0.9173 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2352    0.5222   -2.0514 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6699    0.0019   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2345   -0.8477    0.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    1.2395   -0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5659    1.0901    0.3539 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9205    1.4144   -0.5955 S   0  0  2  0  0  6  0  0  0  0  0  0
    6.4742    1.8079   -1.9459 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5061   -0.0533   -0.8376 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1344    2.2540    0.0190 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    0.7513    1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820   -1.0146    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -0.6104    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412    1.4216   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1875    2.1136    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    2.2919    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    0.5841    2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5921    0.2543   -1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -1.2035    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268   -3.1989   -0.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2221   -2.1525   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -3.1636    0.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -2.2697    1.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6099   -2.0580    0.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7295    1.5430   -1.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419   -0.0638   -1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8892    2.2552   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1876    1.3668   -1.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685    1.1382    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9962    0.3393    2.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338    1.9779    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0485   -0.7816   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6037   -3.0623   -1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3484   -2.6984    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2552   -2.3231   -0.8730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355   -1.9697   -2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238    1.4254   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322    1.7556   -1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030    2.0046    0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9661    1.6948    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 27 26  1  1
 27 30  1  0
 27 28  2  0
 27 29  2  0
 21  2  1  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
  2 18  1  0
 16  6  1  0
  7 18  1  0
 16 10  1  0
 18 52  1  6
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 25 58  1  0
 25 59  1  0
 30 60  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  6
  5 37  1  0
  6 38  1  6
  7 39  1  1
  8 40  1  0
  8 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
M  END

  Mrv1652303102017002D          

 34 37  0  0  1  0            999 V2000
    3.1508    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7280    1.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996    1.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799    1.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315    0.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9436    0.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4754   -0.0044    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0072   -0.6351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1061    0.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8447   -0.5363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8993    2.2548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0584   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4023   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  2  0  0  0  0
  5 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 33  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0092619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(C(=O)COS(O)(=O)=O)[C@@]1(C)C[C@]([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O8S/c1-19-7-5-13(22)9-12(19)3-4-14-15-6-8-21(25,17(24)11-29-30(26,27)28)20(15,2)10-16(23)18(14)19/h9,14-16,18,23,25H,3-8,10-11H2,1-2H3,(H,26,27,28)/t14-,15-,16-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
JOVLCJDINAUYJW-VWUMJDOOSA-N

> <FORMULA>
C21H30O8S

> <MOLECULAR_WEIGHT>
442.52

> <EXACT_MASS>
442.1661391

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.17224708942948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxy}sulfonic acid

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
-0.2353479299673643

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.606899616968494

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.626167896113274

> <JCHEM_PKA_STRONGEST_BASIC>
-2.846864237103005

> <JCHEM_POLAR_SURFACE_AREA>
138.20000000000002

> <JCHEM_REFRACTIVITY>
107.39179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxysulfonic 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  H   UNK     0       5.881   1.583   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.826   3.340   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.453   2.075   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.976   3.524   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.445   0.898   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.961   1.169   0.000  0.00  0.00           O+0
HETATM   11  S   UNK     0      13.954  -0.008   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0      14.947  -1.186   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      15.131   0.984   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.777  -1.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.397   1.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.412   4.209   0.000  0.00  0.00           H+0
HETATM   20  O   UNK     0       3.896   3.938   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.842  -0.136   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       6.351  -1.043   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.811  -0.678   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15   23                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   15                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15    5    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23   33                                             
CONECT   22   21                                                            
CONECT   23   21    2   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   21   27   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(11beta)-11,17-Dihydroxy-21-(sulfooxy)pregn-4-ene-3,20-dione	ChEBI
11,17-Dihydroxy-4-pregnene-3,20-dione-21-yl-sulfate	ChEBI
Cortisol-21-sulfate	ChEBI
(11b)-11,17-Dihydroxy-21-(sulfooxy)pregn-4-ene-3,20-dione	Generator
(11b)-11,17-Dihydroxy-21-(sulphooxy)pregn-4-ene-3,20-dione	Generator
(11beta)-11,17-Dihydroxy-21-(sulphooxy)pregn-4-ene-3,20-dione	Generator
(11Β)-11,17-dihydroxy-21-(sulfooxy)pregn-4-ene-3,20-dione	Generator
(11Β)-11,17-dihydroxy-21-(sulphooxy)pregn-4-ene-3,20-dione	Generator
11,17-Dihydroxy-4-pregnene-3,20-dione-21-yl-sulfuric acid	Generator
11,17-Dihydroxy-4-pregnene-3,20-dione-21-yl-sulphate	Generator
11,17-Dihydroxy-4-pregnene-3,20-dione-21-yl-sulphuric acid	Generator
Cortisol-21-sulfuric acid	Generator
Cortisol-21-sulphate	Generator
Cortisol-21-sulphuric acid	Generator
Cortisol 21-sulfuric acid	Generator
Cortisol 21-sulphate	Generator
Cortisol 21-sulphuric acid	Generator
SS441 Compound	MeSH
Cortisol 21-sulfate, 4-(14)C-labeled	MeSH
4-Pregnen-11,17,21-triol-3,20-dione 21-sulfate	MeSH
Cortisol sulfate	MeSH
F(K)S CPD	MeSH
Cortisol 21-sulfate, 1,2-T2-labeled	MeSH

Chemical Formula

C₂₁H₃₀O₈S

Average Mass

442.5200 Da

Monoisotopic Mass

442.16614 Da

IUPAC Name

{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxy}sulfonic acid

Traditional Name

2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethoxysulfonic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(C(=O)COS(O)(=O)=O)[C@@]1(C)C[C@]([H])(O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O8S/c1-19-7-5-13(22)9-12(19)3-4-14-15-6-8-21(25,17(24)11-29-30(26,27)28)20(15,2)10-16(23)18(14)19/h9,14-16,18,23,25H,3-8,10-11H2,1-2H3,(H,26,27,28)/t14-,15-,16-,18+,19-,20-,21-/m0/s1

InChI Key

JOVLCJDINAUYJW-VWUMJDOOSA-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

Progestogin-skeleton
Sulfated steroid skeleton
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Sulfate-ester
Sulfuric acid monoester
Alkyl sulfate
Sulfuric acid ester
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic alcohol
Organic sulfuric acid or derivatives
Secondary alcohol
Cyclic ketone
Ketone
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:16473 )
3-oxo steroid (CHEBI:16473 )
11beta-hydroxy steroid (CHEBI:16473 )
17alpha-hydroxy steroid (CHEBI:16473 )
20-oxo steroid (CHEBI:16473 )
cortisol ester (CHEBI:16473 )
Sulfates (LMST05020020 )

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	-0.18	ALOGPS
logP	-0.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	-1.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	138.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.39 m³·mol⁻¹	ChemAxon
Polarizability	45.17 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

HMDB0062779

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB034853

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102172

PDB ID

Not Available

ChEBI ID

16473

Good Scents ID

Not Available

References

General References

Hayashi T, Kornel L: Cortisol-21-sulfate (FS) is a specific ligand for intracellular transcortin: demonstration of three types of high affinity corticosteroid binders in bovine aortic cytosol by a combined use of FS and RU 28362. Endocrinology. 1990 Jan;126(1):307-16. doi: 10.1210/endo-126-1-307. [PubMed:2152866 ]
de Rijke E, Zoontjes PW, Samson D, Oostra S, Sterk SS, van Ginkel LA: Investigation of the presence of prednisolone in bovine urine. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2014 Apr;31(4):605-13. doi: 10.1080/19440049.2013.878479. Epub 2014 Mar 3. [PubMed:24392764 ]
Miyabo S, Hisada T: In vitro biosynthesis of cortisol-21-sulfate by various dog tissues. Endocrinology. 1972 May;90(5):1404-6. doi: 10.1210/endo-90-5-1404. [PubMed:5012753 ]
Tamm J, Volkwein U, Voigt KD: [The isolation of cortisol-21-sulfate from the urine of patients with Cushing's syndrome before and after total adrenalectomy]. Experientia. 1964 Nov 15;20(11):601-2. doi: 10.1007/BF02144806. [PubMed:5857563 ]
Kornel L, Patel SK, Ezzeraimi E, Shackleton CH: Corticosteroids in human blood: IX. Evidence for adrenal secretion of sulfate-conjugated cortisol, 11 beta,17 alpha-dihydroxy-4-pregnene-3,20-dione-21-yl-sulfate. Steroids. 1995 Dec;60(12):817-23. doi: 10.1016/0039-128x(95)00141-c. [PubMed:8650705 ]

Showing NP-Card for Cortisol 21-sulfate (NP0092619)

MOL for NP0092619 (Cortisol 21-sulfate)

3D MOL for NP0092619 (Cortisol 21-sulfate)

3D SDF for NP0092619 (Cortisol 21-sulfate)

3D-SDF for NP0092619 (Cortisol 21-sulfate)

PDB for NP0092619 (Cortisol 21-sulfate)

3D PDB for NP0092619 (Cortisol 21-sulfate)

SMILES for NP0092619 (Cortisol 21-sulfate)

INCHI for NP0092619 (Cortisol 21-sulfate)

Structure for NP0092619 (Cortisol 21-sulfate)

3D Structure for NP0092619 (Cortisol 21-sulfate)