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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

enzymes (8) Show 8 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000015

Secondary Accession Numbers

HMDB00015

Metabolite Identification

Common Name

Cortexolone

Description

Cortexolone, also known as cortodoxone or 11-deoxycortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, cortexolone is considered to be a steroid molecule. Cortexolone is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate in the synthesis of cortisol. It was first described by Tadeusz Reichstein in 1938 and named as Substance S. It has also been referred to as Reichstein's Substance S or Compound S. Cortexolone acts as a glucocorticoid, though it is less potent than cortisol. Cortexolone is synthesized from 17alpha-hydroxyprogesterone by 21-hydroxylase and is converted to cortisol by 11beta-hydroxylase. As a result, the level of cortexolone is often measured in patients to diagnose impaired cortisol synthesis, to identify any enzyme deficiency that may be causing impairment along the pathway to cortisol, and to differentiate adrenal disorders. Cortexolone in mammals has limited biological activity and mainly acts as metabolic intermediate within the glucocorticoid pathway, leading to cortisol. On the other hand, in sea lampreys, cortexolone is the major glucocorticoid, with mineralocorticoid activity. Cortexolone in sea lampreys binds to specific corticosteroid receptors and is involved in intestinal osmoregulation and in sea lamprey at metamorphosis, a process in which they develop seawater tolerance before downstream migration.

Structure

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


  Mrv1652303182019222D          

 28 31  0  0  0  0            999 V2000
10001.078110001.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.940610000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7988 9997.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.7729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.366610000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9998.7729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2268 9999.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5123 9999.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5123 9998.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2268 9997.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9413 9998.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9413 9999.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.366010000.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651510000.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6532 9999.5938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6532 9997.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3677 9998.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3677 9999.1813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.080510000.4276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0805 9999.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8651 9999.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.350010000.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865110000.6826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.865110001.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.578810001.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149510001.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.578810001.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.293410001.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15  4  1  6  0  0  0
 18  5  1  1  0  0  0
  9  3  2  0  0  0  0
 15 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12  2  1  1  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  6  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 18 20  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

HMDB0000015
     RDKit          3D
Cortexolone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.0371    0.0070    1.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.1190    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9552   -1.3413   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.2159   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.0291   -0.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4016    1.0718    0.1682 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1942    2.3579   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    2.2293    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216    0.9223    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.9086    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1480   -0.3310    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -0.6103    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7511   -1.2796   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.0848   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -0.3258    0.1302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2884   -1.2350    1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    1.0761   -0.4188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8600    2.1863   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100    1.5954   -0.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.0824   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7816   -0.1814   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5779   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4834   -0.4368    1.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.4366   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1110   -1.9607   -0.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -1.0084    1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231    0.1490    2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    0.8259    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -2.0211   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -1.9245    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.3420   -1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560   -2.1305   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677    0.4502   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.8744    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    3.1787    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.4976   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0946    2.3319    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332    3.0507    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380    1.8254    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878   -1.1785   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -2.3114    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5705   -1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.0900   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -0.9949    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -1.1283    1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832   -2.2956    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.9229   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897    2.5439    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    3.0456   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991    2.0329   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9389    1.8503    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493   -1.1342   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -2.2082   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934   -0.7576   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4733   -2.7554   -0.7442 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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  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
  8 38  1  0
 10 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END


  Mrv1652303182019222D          

 28 31  0  0  0  0            999 V2000
10001.078110001.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.940610000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7988 9997.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.7729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.366610000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9998.7729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2268 9999.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5123 9999.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5123 9998.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2268 9997.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9413 9998.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9413 9999.1798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.366010000.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651510000.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6532 9999.5938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6532 9997.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3677 9998.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3677 9999.1813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.080510000.4276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0805 9999.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8651 9999.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.350010000.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865110000.6826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.865110001.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.578810001.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149510001.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.578810001.0951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.293410001.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15  4  1  6  0  0  0
 18  5  1  1  0  0  0
  9  3  2  0  0  0  0
 15 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12  2  1  1  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  6  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 13 19  1  0  0  0  0
 20  6  1  6  0  0  0
 19  1  1  1  0  0  0
 18 20  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000015

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1

> <INCHI_KEY>
WHBHBVVOGNECLV-OBQKJFGGSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.4605

> <EXACT_MASS>
346.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.86084842151295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.5839312316666665

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.905648730473413

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.591037618857374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.329982616090181

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
95.80749999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000015
     RDKit          3D
Cortexolone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.0371    0.0070    1.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.1190    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9552   -1.3413   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.2159   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.0291   -0.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4016    1.0718    0.1682 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1942    2.3579   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    2.2293    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216    0.9223    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.9086    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1480   -0.3310    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -0.6103    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7511   -1.2796   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.0848   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -0.3258    0.1302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2884   -1.2350    1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    1.0761   -0.4188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8600    2.1863   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100    1.5954   -0.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.0824   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7816   -0.1814   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5779   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4834   -0.4368    1.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.4366   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1110   -1.9607   -0.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -1.0084    1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231    0.1490    2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    0.8259    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -2.0211   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -1.9245    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.3420   -1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560   -2.1305   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677    0.4502   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.8744    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    3.1787    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.4976   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0946    2.3319    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332    3.0507    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380    1.8254    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878   -1.1785   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -2.3114    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5705   -1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.0900   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -0.9949    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -1.1283    1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832   -2.2956    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.9229   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897    2.5439    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    3.0456   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991    2.0329   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9389    1.8503    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493   -1.1342   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -2.2082   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934   -0.7576   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4733   -2.7554   -0.7442 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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  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
  8 38  1  0
 10 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8668.6798669.014   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.6898666.681   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8660.6918662.820   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8666.0198664.376   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8667.3518666.681   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8668.6798664.376   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8663.3578665.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0238665.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0238663.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3578662.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6908663.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6908665.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3508668.235   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.0168667.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.0198665.908   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0198662.828   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3538663.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3538665.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6848667.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6848665.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.1488665.449   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.0538666.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.1488667.941   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.1488669.481   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.4808670.251   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8668.8128670.251   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0    8671.4808668.711   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0    8672.8148669.481   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   12                                                            
CONECT    3    9                                                            
CONECT    4   15                                                            
CONECT    5   18                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12    7   11   15    2                                             
CONECT   13   14   19                                                       
CONECT   14   13   15                                                       
CONECT   15   18   14    4   12                                             
CONECT   16   17   11                                                       
CONECT   17   16   18                                                       
CONECT   18   15   17    5   20                                             
CONECT   19   20   23   13    1                                             
CONECT   20   19   21    6   18                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   27   19   22                                             
CONECT   24   23   25   26                                                  
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0000015
HETATM    1  C1  UNL     1      -2.037   0.007   1.565  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.713  -0.119   0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.955  -1.341  -0.185  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.346  -1.216  -0.862  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.178  -0.029  -0.566  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.402   1.072   0.168  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.194   2.358  -0.093  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.440   2.229   0.757  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.122   0.922   0.578  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.427   0.909   0.854  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.148  -0.331   0.700  1.00  0.00           C  
HETATM   12  O1  UNL     1       6.115  -0.610   1.450  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.751  -1.280  -0.345  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.352  -1.085  -0.859  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.480  -0.326   0.130  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.288  -1.235   1.325  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.937   1.076  -0.419  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.860   2.186  -0.149  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.210   1.595  -0.581  1.00  0.00           C  
HETATM   20  C19 UNL     1      -2.978   0.082  -0.686  1.00  0.00           C  
HETATM   21  O2  UNL     1      -2.782  -0.181  -2.040  1.00  0.00           O  
HETATM   22  C20 UNL     1      -4.172  -0.578  -0.144  1.00  0.00           C  
HETATM   23  O3  UNL     1      -4.483  -0.437   1.012  1.00  0.00           O  
HETATM   24  C21 UNL     1      -5.040  -1.437  -0.978  1.00  0.00           C  
HETATM   25  O4  UNL     1      -6.111  -1.961  -0.270  1.00  0.00           O  
HETATM   26  H1  UNL     1      -2.408  -1.008   1.896  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.123   0.149   2.213  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.705   0.826   1.830  1.00  0.00           H  
HETATM   29  H4  UNL     1      -1.618  -2.021  -0.800  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.818  -1.925   0.774  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.179  -1.342  -1.974  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.956  -2.131  -0.595  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.468   0.450  -1.549  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.498   0.874   1.235  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.576   3.179   0.341  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.412   2.498  -1.156  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.095   2.332   1.824  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.133   3.051   0.522  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.938   1.825   1.194  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.488  -1.179  -1.182  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.923  -2.311   0.062  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.418  -0.571  -1.839  1.00  0.00           H  
HETATM   43  H18 UNL     1       2.933  -2.090  -1.054  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.022  -0.995   2.139  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.282  -1.128   1.781  1.00  0.00           H  
HETATM   46  H21 UNL     1       2.483  -2.296   1.054  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.862   0.923  -1.515  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.890   2.544   0.886  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.609   3.046  -0.825  1.00  0.00           H  
HETATM   50  H25 UNL     1      -3.499   2.033  -1.539  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.939   1.850   0.190  1.00  0.00           H  
HETATM   52  H27 UNL     1      -2.849  -1.134  -2.266  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.481  -2.208  -1.539  1.00  0.00           H  
HETATM   54  H29 UNL     1      -5.493  -0.758  -1.758  1.00  0.00           H  
HETATM   55  H30 UNL     1      -6.473  -2.755  -0.744  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   17   20
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   15   33
CONECT    6    7   17   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   10   15
CONECT   10   11   39
CONECT   11   12   12   13
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16
CONECT   16   44   45   46
CONECT   17   18   47
CONECT   18   19   48   49
CONECT   19   20   50   51
CONECT   20   21   22
CONECT   21   52
CONECT   22   23   23   24
CONECT   24   25   53   54
CONECT   25   55
END

HMDB0000015
     RDKit          3D
Cortexolone
 55 58  0  0  0  0  0  0  0  0999 V2000
   -2.0371    0.0070    1.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.1190    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9552   -1.3413   -0.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.2159   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.0291   -0.5657 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4016    1.0718    0.1682 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1942    2.3579   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    2.2293    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1216    0.9223    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.9086    0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1480   -0.3310    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149   -0.6103    1.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7511   -1.2796   -0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.0848   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4804   -0.3258    0.1302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2884   -1.2350    1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    1.0761   -0.4188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8600    2.1863   -0.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100    1.5954   -0.5809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    0.0824   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7816   -0.1814   -2.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1722   -0.5779   -0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4834   -0.4368    1.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.4366   -0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1110   -1.9607   -0.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080   -1.0084    1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231    0.1490    2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7051    0.8259    1.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -2.0211   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8184   -1.9245    0.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1786   -1.3420   -1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560   -2.1305   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677    0.4502   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.8744    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    3.1787    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    2.4976   -1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0946    2.3319    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332    3.0507    0.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9380    1.8254    1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4878   -1.1785   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9225   -2.3114    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4183   -0.5705   -1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.0900   -1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -0.9949    2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -1.1283    1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4832   -2.2956    1.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.9229   -1.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897    2.5439    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    3.0456   -0.8245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4991    2.0329   -1.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9389    1.8503    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493   -1.1342   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -2.2082   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4934   -0.7576   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4733   -2.7554   -0.7442 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
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  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
  8 38  1  0
 10 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  6
 18 48  1  0
 18 49  1  0
 19 50  1  0
 19 51  1  0
 21 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Desoxy-17-hydroxycorticosterone	ChEBI
Cortodoxone	ChEBI
Reichstein substance S	HMDB
Substance S, reichstein's	HMDB
11 Deoxycortisol	HMDB
11 Desoxycortisol	HMDB
11 Desoxycortisone	HMDB
S, Reichstein's substance	HMDB
11-Desoxycortisol	HMDB
11-Desoxycortisone	HMDB
Reichsteins substance S	HMDB
11-Deoxycortisol	HMDB
SK&F 3050	HMDB
Reichstein's substance S	HMDB
11-Deoxy-17-hydroxycorticosterone	HMDB
11-Deoxyhydrocortisone	HMDB
11-Desoxyhydrocortisone	HMDB
17,21-Dihydroxy-4-pregnene-3,20-dione	HMDB
17,21-Dihydroxypregn-4-ene-3,20-dione	HMDB
17,21-Dihydroxyprogesterone	HMDB
17-Hydroxy-11-deoxycorticosterone	HMDB
17alpha-Hydroxycortexone	HMDB
20-Dione 17,21-dihydroxypregn-4-ene-3	HMDB
4-Pregnene-17alpha,21-diol-3,20-dione	HMDB
Compound S	HMDB
11-Deoxy-17-hydrocorticosterone	HMDB
11-Deoxycortisone	HMDB
11-Desoxy-17α-hydroxycorticosterone	HMDB
11-Desoxy-17alpha-hydroxycorticosterone	HMDB
17,21-Dihydroxypregn-4-en-3,20-dione	HMDB
17Α,21-dihydroxy-4-pregnen-3,20-dione	HMDB
17Α,21-dihydroxypregn-4-ene-3,20-dione	HMDB
17Α,21-dihydroxyprogesterone	HMDB
17Α-hydroxycortexone	HMDB
4-Pregnen-17α,21-diol-3,20-dione	HMDB
4-Pregnene-17α,21-diol-3,20-dione	HMDB
17alpha,21-Dihydroxy-4-pregnen-3,20-dione	HMDB
17alpha,21-Dihydroxypregn-4-ene-3,20-dione	HMDB
17alpha,21-Dihydroxyprogesterone	HMDB
4-Pregnen-17alpha,21-diol-3,20-dione	HMDB
Cortexolone	MeSH

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

152-58-9

SMILES

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

InChI Identifier

InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1

InChI Key

WHBHBVVOGNECLV-OBQKJFGGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

21-hydroxysteroid
Progestogin-skeleton
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

glucocorticoid (CHEBI:28324 )
deoxycortisol (CHEBI:28324 )
Glucocorticoids (C05488 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05488 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030086 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Hyperphenylalaninemia ( PMID: 8933406.0 )

Disposition

Source

Exogenous

Food

Animal origin

Bovine

Beefalo ( FooDB (FOOD00530) )

Caprae

Domestic goat ( FooDB (FOOD00529) )

Equine

Horse ( FooDB (FOOD00378) )

Ovis

Sheep (Mutton, Lamb) ( FooDB (FOOD00473) )

Swine

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

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Multicellular process

Coagulation

Role

Industrial application

Pharmaceutical industry

Biomarker

Diagnostic biomarker ( PMID: 8933406.0 )

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.08	SANGSTER (1994)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	187.356	30932474
[M+H]+	Not Available	187.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002182

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.58	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.81 m³·mol⁻¹	ChemAxon
Polarizability	38.86 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
AllCCS	[M+H]+	185.795	32859911
AllCCS	[M-H]-	189.967	32859911
DeepCCS	[M-2H]-	215.514	30932474
DeepCCS	[M+Na]+	190.9	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cortexolone	[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3199.8	Standard polar	33892256
Cortexolone	[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2850.9	Standard non polar	33892256
Cortexolone	[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3169.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cortexolone,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO	3267.0	Semi standard non polar	33892256
Cortexolone,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C	3242.6	Semi standard non polar	33892256
Cortexolone,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C	3149.9	Semi standard non polar	33892256
Cortexolone,1TMS,isomer #4	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO	3146.2	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3319.2	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO	3191.6	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3226.8	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #4	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=O)CO[Si](C)(C)C	3169.1	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #5	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3232.0	Semi standard non polar	33892256
Cortexolone,2TMS,isomer #6	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO)O[Si](C)(C)C	3085.5	Semi standard non polar	33892256
Cortexolone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3251.7	Semi standard non polar	33892256
Cortexolone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3141.0	Standard non polar	33892256
Cortexolone,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=O)CO[Si](C)(C)C	3453.7	Standard polar	33892256
Cortexolone,3TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3296.5	Semi standard non polar	33892256
Cortexolone,3TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3032.1	Standard non polar	33892256
Cortexolone,3TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3438.2	Standard polar	33892256
Cortexolone,3TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3156.0	Semi standard non polar	33892256
Cortexolone,3TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3061.3	Standard non polar	33892256
Cortexolone,3TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO)O[Si](C)(C)C	3477.0	Standard polar	33892256
Cortexolone,3TMS,isomer #4	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3133.4	Semi standard non polar	33892256
Cortexolone,3TMS,isomer #4	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3111.3	Standard non polar	33892256
Cortexolone,3TMS,isomer #4	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3516.9	Standard polar	33892256
Cortexolone,4TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3190.0	Semi standard non polar	33892256
Cortexolone,4TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3134.5	Standard non polar	33892256
Cortexolone,4TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@]2(O[Si](C)(C)C)C(=CO[Si](C)(C)C)O[Si](C)(C)C	3412.4	Standard polar	33892256
Cortexolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@]1(C(=O)CO)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3511.9	Semi standard non polar	33892256
Cortexolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3514.0	Semi standard non polar	33892256
Cortexolone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3408.9	Semi standard non polar	33892256
Cortexolone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O)(C(=O)CO)[C@@]3(C)CC[C@@H]12	3429.4	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3822.7	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=CO)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3735.3	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O[Si](C)(C)C(C)(C)C)(C(=O)CO)[C@@]3(C)CC[C@@H]12	3702.5	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3734.5	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3695.6	Semi standard non polar	33892256
Cortexolone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O)(C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3580.2	Semi standard non polar	33892256
Cortexolone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	4015.9	Semi standard non polar	33892256
Cortexolone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3703.9	Standard non polar	33892256
Cortexolone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3696.0	Standard polar	33892256
Cortexolone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3980.7	Semi standard non polar	33892256
Cortexolone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3795.9	Standard non polar	33892256
Cortexolone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3704.4	Standard polar	33892256
Cortexolone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3900.6	Semi standard non polar	33892256
Cortexolone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3673.6	Standard non polar	33892256
Cortexolone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@](O[Si](C)(C)C(C)(C)C)(C(=CO)O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3742.2	Standard polar	33892256
Cortexolone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3861.5	Semi standard non polar	33892256
Cortexolone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3720.1	Standard non polar	33892256
Cortexolone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3802.1	Standard polar	33892256
Cortexolone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	4155.3	Semi standard non polar	33892256
Cortexolone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3882.7	Standard non polar	33892256
Cortexolone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3670.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Cortexolone GC-MS (2 MEOX; 2 TMS)	splash10-0fau-4920000000-b369d2b097d724e4d6d6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cortexolone GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone LC-ESI-qTof , Positive-QTOF	splash10-0a4j-3931000000-0d5b4b35af4fb7259e0b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone , positive-QTOF	splash10-0a4j-3931000000-0d5b4b35af4fb7259e0b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 10V, Positive-QTOF	splash10-0002-0009000000-3a7012051ab6d4bf0562	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 20V, Positive-QTOF	splash10-052b-7954000000-8b08129e96f27aa17d97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 10V, Negative-QTOF	splash10-014i-0009000000-42c6be6599289f724a27	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 40V, Positive-QTOF	splash10-052b-6900000000-e4a3639328e2024d0e8f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 20V, Negative-QTOF	splash10-014i-0009000000-bb32ffe5ad4a80ab7c5a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cortexolone 40V, Negative-QTOF	splash10-0002-0390000000-d6fdb36b0e90c40b94cb	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 10V, Positive-QTOF	splash10-002b-0029000000-4461b817ffbd52446693	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 20V, Positive-QTOF	splash10-0cfs-0198000000-95e4ea654010492c731e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 40V, Positive-QTOF	splash10-01c9-0390000000-2c12ac25b2d03a951073	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 10V, Negative-QTOF	splash10-0002-0019000000-8ffa4f9a93205a223d67	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 20V, Negative-QTOF	splash10-000i-3089000000-630c1ceb5066f51ae904	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 40V, Negative-QTOF	splash10-0a4i-6091000000-520f7455eb4f28362eb9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 10V, Positive-QTOF	splash10-0002-0009000000-6e67f0e99b733343d1e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 20V, Positive-QTOF	splash10-08i0-0901000000-78c126f772ed1698f472	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 40V, Positive-QTOF	splash10-002g-3930000000-d7d52250ebc31a93ab06	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 10V, Negative-QTOF	splash10-01pa-0049000000-bba8b14791a1510eb866	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 20V, Negative-QTOF	splash10-00kr-0096000000-364c61e7a9193d6a16fb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cortexolone 40V, Negative-QTOF	splash10-00kr-0090000000-96af9df83c9954436093	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Mitochondria
Endoplasmic reticulum

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

All Tissues

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0039 +/- 0.0004 uM	Adult (>18 years old)	Both	Normal	8890720	details
Blood	Detected and Quantified	<0.0250 uM	Not Specified	Both	Normal	8933406	details
Blood	Detected and Quantified	<0.0600 uM	Newborn (0-30 days old)	Both	Normal	8933406	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	28701177	details
Urine	Detected and Quantified	0.017-178.9 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	3515819	details
Urine	Detected and Quantified	0.02 (0.0091-0.032) umol/mmol creatinine	Adult (>18 years old)	Female	Normal	6296182	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.3 uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	8933406	details
Blood	Detected and Quantified	1.84 uM	Infant (0-1 year old)	Female	11-beta-hydroxylase deficiency	8933406	details
Blood	Detected and Quantified	0.00790-0.329 uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	8933406	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Sepsis	28701177	details

Associated Disorders and Diseases

Disease References

11-beta-Hydroxylase deficiency
Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
Sepsis
Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]

Associated OMIM IDs

202010 (11-beta-Hydroxylase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021872

KNApSAcK ID

Not Available

Chemspider ID

389582

KEGG Compound ID

C05488

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28324

Food Biomarker Ontology

Not Available

VMH ID

11DOCRTSL

MarkerDB ID

MDB00013414

Good Scents ID

Not Available

References

Synthesis Reference

Luu, Duc Huy. New method for the synthesis of Reichstein's compound S from pregnene. Tap Chi Duoc Hoc (2002), (9), 23-25.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

White PC, Dupont J, New MI, Leiberman E, Hochberg Z, Rosler A: A mutation in CYP11B1 (Arg-448----His) associated with steroid 11 beta-hydroxylase deficiency in Jews of Moroccan origin. J Clin Invest. 1991 May;87(5):1664-7. [PubMed:2022736 ]
White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
Curnow KM, Tusie-Luna MT, Pascoe L, Natarajan R, Gu JL, Nadler JL, White PC: The product of the CYP11B2 gene is required for aldosterone biosynthesis in the human adrenal cortex. Mol Endocrinol. 1991 Oct;5(10):1513-22. [PubMed:1775135 ]
Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. [PubMed:14709852 ]
Trakakis E, Laggas D, Salamalekis E, Creatsas G: 21-Hydroxylase deficiency: from molecular genetics to clinical presentation. J Endocrinol Invest. 2005 Feb;28(2):187-92. [PubMed:15887869 ]
Krone N, Riepe FG, Gotze D, Korsch E, Rister M, Commentz J, Partsch CJ, Grotzinger J, Peter M, Sippell WG: Congenital adrenal hyperplasia due to 11-hydroxylase deficiency: functional characterization of two novel point mutations and a three-base pair deletion in the CYP11B1 gene. J Clin Endocrinol Metab. 2005 Jun;90(6):3724-30. Epub 2005 Mar 8. [PubMed:15755848 ]
Adinoff B, Krebaum SR, Chandler PA, Ye W, Brown MB, Williams MJ: Dissection of hypothalamic-pituitary-adrenal axis pathology in 1-month-abstinent alcohol-dependent men, part 1: adrenocortical and pituitary glucocorticoid responsiveness. Alcohol Clin Exp Res. 2005 Apr;29(4):517-27. [PubMed:15834216 ]
Brown JR, Cavanaugh AH, Farnsworth WE: A simple radioimmunoassay for plasma cortisol and 11-deoxycortisol (17, 21-dihydroxy-4-pregnene-3, 20-dione). Steroids. 1976 Oct;28(4):487-98. [PubMed:1034356 ]
den Brinker M, Joosten KF, Liem O, de Jong FH, Hop WC, Hazelzet JA, van Dijk M, Hokken-Koelega AC: Adrenal insufficiency in meningococcal sepsis: bioavailable cortisol levels and impact of interleukin-6 levels and intubation with etomidate on adrenal function and mortality. J Clin Endocrinol Metab. 2005 Sep;90(9):5110-7. Epub 2005 Jun 28. [PubMed:15985474 ]
Lee HH, Won GS, Chao HT, Lee YJ, Chung BC: Novel missense mutations, GCC [Ala306]- > GTC [Val] and ACG [Thr318]- > CCG [Pro], in the CYP11B1 gene cause steroid 11beta-hydroxylase deficiency in the Chinese. Clin Endocrinol (Oxf). 2005 Apr;62(4):418-22. [PubMed:15807871 ]
Zachmann M, Tassinari D, Prader A: Clinical and biochemical variability of congenital adrenal hyperplasia due to 11 beta-hydroxylase deficiency. A study of 25 patients. J Clin Endocrinol Metab. 1983 Feb;56(2):222-9. [PubMed:6296182 ]
Bradshaw KD, Milewich L, Mason JI, Parker CR Jr, MacDonald PC, Carr BR: Steroid secretory characteristics of a virilizing adrenal adenoma in a woman. J Endocrinol. 1994 Feb;140(2):297-307. [PubMed:8169562 ]
Bureik M, Bruck N, Hubel K, Bernhardt R: The human mineralocorticoid receptor only partially differentiates between different ligands after expression in fission yeast. FEMS Yeast Res. 2005 Apr;5(6-7):627-33. [PubMed:15780662 ]
Dragan CA, Zearo S, Hannemann F, Bernhardt R, Bureik M: Efficient conversion of 11-deoxycortisol to cortisol (hydrocortisone) by recombinant fission yeast Schizosaccharomyces pombe. FEMS Yeast Res. 2005 Apr;5(6-7):621-5. [PubMed:15780661 ]
Sakamoto N, Matsukura S, Tsuboi S, Tokumiya T, Imura H: Radioimmunoassay for 11-deoxycortisol using iodine-labeled tracer. Endocrinol Jpn. 1976 Aug;23(4):359-63. [PubMed:1024042 ]
Tjeerdsma G, Sluiter WJ, Hew JM, Molenaar WM, de Lange WE, Dullaart RP: Hyperprolactinaemia is associated with a higher prevalence of pituitary-adrenal dysfunction in non-functioning pituitary macroadenoma. Eur J Endocrinol. 1996 Sep;135(3):299-308. [PubMed:8890720 ]
Hughes IA, Arisaka O, Perry LA, Honour JW: Early diagnosis of 11 beta-hydroxylase deficiency in two siblings confirmed by analysis of a novel steroid metabolite in newborn urine. Acta Endocrinol (Copenh). 1986 Mar;111(3):349-54. [PubMed:3515819 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

Reactions

Cortexolone + Reduced ferredoxin + Oxygen → Cortisol + Oxidized ferredoxin + Water	details

References

Curnow KM, Tusie-Luna MT, Pascoe L, Natarajan R, Gu JL, Nadler JL, White PC: The product of the CYP11B2 gene is required for aldosterone biosynthesis in the human adrenal cortex. Mol Endocrinol. 1991 Oct;5(10):1513-22. [PubMed:1775135 ]

Enzyme Details

2. Mineralocorticoid receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:: NR3C2
Uniprot ID:: P08235
Molecular weight:: 107066.6

Enzyme Details

3. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NAD	details

Enzyme Details

4. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

Cortexolone + Hydrogen Ion + NADH → 17alpha,21-Dihydroxypregnenolone + NAD	details

Enzyme Details

5. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

Reactions

Cortexolone + Reduced ferredoxin + Oxygen → Cortisol + Oxidized ferredoxin + Water	details

Enzyme Details

6. Cytochrome P450 21-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: P450-CYP21B
Uniprot ID:: Q16874
Molecular weight:: 56000.9

Enzyme Details

7. Cytochrome P450, family 21, subfamily A, polypeptide 2

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP21A2
Uniprot ID:: Q08AG9
Molecular weight:: 55972.9

Enzyme Details

8. Steroid 21-hydroxylase

General function:: Not Available
Specific function:: Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:: CYP21A2
Uniprot ID:: P08686
Molecular weight:: 56000.94

Reactions

17-Hydroxyprogesterone + Reduced acceptor + Oxygen → Cortexolone + Acceptor + Water	details

Showing metabocard for Cortexolone (HMDB0000015)

MOL for HMDB0000015 (Cortexolone)

3D MOL for HMDB0000015 (Cortexolone)

3D SDF for HMDB0000015 (Cortexolone)

3D-SDF for HMDB0000015 (Cortexolone)

PDB for HMDB0000015 (Cortexolone)

3D PDB for HMDB0000015 (Cortexolone)

SMILES for HMDB0000015 (Cortexolone)

INCHI for HMDB0000015 (Cortexolone)

Structure for HMDB0000015 (Cortexolone)

3D Structure for HMDB0000015 (Cortexolone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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References

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