You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:03 UTC

HMDB ID

HMDB0000903

Secondary Accession Numbers

HMDB00903

Metabolite Identification

Common Name

Tetrahydrocortisone

Description

Cortisol is a corticosteroid hormone that is involved in the response to stress; it increases blood pressure and blood sugar levels and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation. -- Wikipedia ; As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. -- Wikipedia .

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Tetrahydrofuran.mol
  Mrv1652305271900302D          

 30 33  0  0  0  0            999 V2000
   -2.3857   -1.5496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3857   -0.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -0.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -1.5496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2423   -1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -0.7246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1866   -0.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9712   -0.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712    0.7678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7137    1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    2.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866    0.5129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1866    1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    0.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -0.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9568   -0.7246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9568    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1002   -1.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    1.1165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002    2.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568    0.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9168    2.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -2.3746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -1.1371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    0.1004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -1.1371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 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  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
  1 22  1  1  0  0  0
 12 23  1  6  0  0  0
 14 24  1  0  0  0  0
 18 25  2  0  0  0  0
 13 26  2  0  0  0  0
  5 27  1  6  0  0  0
 19 28  1  6  0  0  0
  8 29  1  1  0  0  0
  9 30  1  6  0  0  0
M  END

Tetrahydrofuran.mol
  Mrv1652305271900302D          

 30 33  0  0  0  0            999 V2000
   -2.3857   -1.5496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3857   -0.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -0.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -1.5496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2423   -1.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722   -0.7246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1866   -0.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9712   -0.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4562    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712    0.7678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7137    1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033    2.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866    0.5129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1866    1.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    0.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -0.3121    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9568   -0.7246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9568    0.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1002   -1.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7189    1.1165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1002    2.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568    0.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9168    2.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -2.3746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423   -1.1371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    0.1004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1866   -1.1371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 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  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
  1 22  1  1  0  0  0
 12 23  1  6  0  0  0
 14 24  1  0  0  0  0
 18 25  2  0  0  0  0
 13 26  2  0  0  0  0
  5 27  1  6  0  0  0
 19 28  1  6  0  0  0
  8 29  1  1  0  0  0
  9 30  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000903

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
SYGWGHVTLUBCEM-SDYDLROXSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.4758

> <EXACT_MASS>
364.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.47223298033221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.4990142216666678

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.904492965642536

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.576202868308023

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569620405321663

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
96.67619999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:57})
 58 61  0  0  0  0  0  0  0  0999 V2000
   -0.9519    1.4982   -1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    1.3568   -0.5536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8813    2.4561    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    2.0213   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.4931   -0.5270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5966    0.1965   -1.8875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2312   -0.2132    0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    0.3015    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884   -1.5617    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6636   -2.0209    1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378    0.0796   -0.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6986   -0.2552    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -1.0575   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -1.1907   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -2.2685   -0.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    0.0405   -0.7073 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.3540   -1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    1.1932    0.0423 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2586    0.9314    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    2.4488   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    2.1872    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.0107   -0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4373    1.2526   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6236    0.7389    0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204   -0.4243   -0.1748 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4812   -0.1676   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -0.6785    0.4519 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -1.6754   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950   -1.4032   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.2293   -0.0270 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1738   -0.5952    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7465    2.4776    1.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    3.4271   -0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    2.2476    0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534    2.5323   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.4720   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3420   -1.4775   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9701   -2.2709   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0597   -2.8854    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -1.0760    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.5485    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563    0.6208    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123   -1.9836   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930   -0.8219   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    2.6877   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333    3.2816    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2092    3.0772    0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    1.9558    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478    1.6301    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629    0.4824    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0774   -1.4052    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -2.5031   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860   -1.9336    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -1.1449   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -2.2948   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1352   -0.7933    1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808    0.2322    1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.4853    1.5045 H   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
  2 11  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4  5  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 36  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 13 14  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 22  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 30  1  0  0  0  0
 24 25  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 27 51  1  0  0  0  0
 28 29  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 29 30  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
 30 31  1  1  0  0  0
 31 56  1  0  0  0  0
 31 57  1  0  0  0  0
 31 58  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Tetrahydrofuran.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.453  -2.893   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.453  -1.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.120  -0.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.120  -3.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.786  -2.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.452  -3.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.881  -2.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.881  -1.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.215  -0.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.680  -1.059   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.585   0.187   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.680   1.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.199   3.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.299   4.433   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.215   0.957   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.215   2.497   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.881   1.727   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.452   0.957   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.452  -0.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.786  -1.353   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.786   0.187   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.787  -3.663   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.075   2.084   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.787   4.034   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.786   1.727   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.711   3.787   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -1.786  -4.433   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.452  -2.123   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.881   0.187   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.215  -2.123   0.000  0.00  0.00           H+0
CONECT    1    2    4   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2   20                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   20   27                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   29                                             
CONECT    9    8   10   15   30                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15   23                                             
CONECT   13   12   14   26                                                  
CONECT   14   13   24                                                       
CONECT   15   12    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18    8   20   28                                             
CONECT   20   19    3    5   21                                             
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23   12                                                            
CONECT   24   14                                                            
CONECT   25   18                                                            
CONECT   26   13                                                            
CONECT   27    5                                                            
CONECT   28   19                                                            
CONECT   29    8                                                            
CONECT   30    9                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -0.952   1.498  -1.632  1.00  0.00           H  
HETATM    2  C   UNL     1      -1.018   1.357  -0.554  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.881   2.456   0.078  1.00  0.00           C  
HETATM    4  C   UNL     1      -3.326   2.021  -0.286  1.00  0.00           C  
HETATM    5  C   UNL     1      -3.275   0.493  -0.527  1.00  0.00           C  
HETATM    6  O   UNL     1      -3.597   0.197  -1.887  1.00  0.00           O  
HETATM    7  C   UNL     1      -4.231  -0.213   0.400  1.00  0.00           C  
HETATM    8  O   UNL     1      -4.551   0.301   1.444  1.00  0.00           O  
HETATM    9  C   UNL     1      -4.788  -1.562   0.022  1.00  0.00           C  
HETATM   10  O   UNL     1      -5.664  -2.021   1.054  1.00  0.00           O  
HETATM   11  C   UNL     1      -1.838   0.080  -0.221  1.00  0.00           C  
HETATM   12  C   UNL     1      -1.699  -0.255   1.265  1.00  0.00           C  
HETATM   13  C   UNL     1      -1.286  -1.058  -1.065  1.00  0.00           C  
HETATM   14  C   UNL     1       0.188  -1.191  -0.707  1.00  0.00           C  
HETATM   15  O   UNL     1       0.654  -2.268  -0.426  1.00  0.00           O  
HETATM   16  C   UNL     1       1.056   0.041  -0.707  1.00  0.00           C  
HETATM   17  H   UNL     1       1.233   0.354  -1.736  1.00  0.00           H  
HETATM   18  C   UNL     1       0.364   1.193   0.042  1.00  0.00           C  
HETATM   19  H   UNL     1       0.259   0.931   1.095  1.00  0.00           H  
HETATM   20  C   UNL     1       1.223   2.449  -0.092  1.00  0.00           C  
HETATM   21  C   UNL     1       2.587   2.187   0.554  1.00  0.00           C  
HETATM   22  C   UNL     1       3.276   1.011  -0.137  1.00  0.00           C  
HETATM   23  H   UNL     1       3.437   1.253  -1.188  1.00  0.00           H  
HETATM   24  C   UNL     1       4.624   0.739   0.534  1.00  0.00           C  
HETATM   25  C   UNL     1       5.320  -0.424  -0.175  1.00  0.00           C  
HETATM   26  H   UNL     1       5.481  -0.168  -1.222  1.00  0.00           H  
HETATM   27  O   UNL     1       6.579  -0.678   0.452  1.00  0.00           O  
HETATM   28  C   UNL     1       4.444  -1.675  -0.085  1.00  0.00           C  
HETATM   29  C   UNL     1       3.095  -1.403  -0.753  1.00  0.00           C  
HETATM   30  C   UNL     1       2.395  -0.229  -0.027  1.00  0.00           C  
HETATM   31  C   UNL     1       2.174  -0.595   1.442  1.00  0.00           C  
HETATM   32  H   UNL     1      -1.746   2.478   1.160  1.00  0.00           H  
HETATM   33  H   UNL     1      -1.650   3.427  -0.359  1.00  0.00           H  
HETATM   34  H   UNL     1      -4.003   2.248   0.538  1.00  0.00           H  
HETATM   35  H   UNL     1      -3.653   2.532  -1.191  1.00  0.00           H  
HETATM   36  H   UNL     1      -4.485   0.472  -2.151  1.00  0.00           H  
HETATM   37  H   UNL     1      -5.342  -1.478  -0.913  1.00  0.00           H  
HETATM   38  H   UNL     1      -3.970  -2.271  -0.102  1.00  0.00           H  
HETATM   39  H   UNL     1      -6.060  -2.885   0.878  1.00  0.00           H  
HETATM   40  H   UNL     1      -2.370  -1.076   1.517  1.00  0.00           H  
HETATM   41  H   UNL     1      -0.670  -0.548   1.477  1.00  0.00           H  
HETATM   42  H   UNL     1      -1.956   0.621   1.860  1.00  0.00           H  
HETATM   43  H   UNL     1      -1.812  -1.984  -0.833  1.00  0.00           H  
HETATM   44  H   UNL     1      -1.393  -0.822  -2.124  1.00  0.00           H  
HETATM   45  H   UNL     1       1.358   2.688  -1.147  1.00  0.00           H  
HETATM   46  H   UNL     1       0.733   3.282   0.413  1.00  0.00           H  
HETATM   47  H   UNL     1       3.209   3.077   0.459  1.00  0.00           H  
HETATM   48  H   UNL     1       2.449   1.956   1.610  1.00  0.00           H  
HETATM   49  H   UNL     1       5.248   1.630   0.470  1.00  0.00           H  
HETATM   50  H   UNL     1       4.463   0.482   1.581  1.00  0.00           H  
HETATM   51  H   UNL     1       7.077  -1.405   0.053  1.00  0.00           H  
HETATM   52  H   UNL     1       4.940  -2.503  -0.592  1.00  0.00           H  
HETATM   53  H   UNL     1       4.286  -1.934   0.962  1.00  0.00           H  
HETATM   54  H   UNL     1       3.253  -1.145  -1.800  1.00  0.00           H  
HETATM   55  H   UNL     1       2.471  -2.295  -0.689  1.00  0.00           H  
HETATM   56  H   UNL     1       3.135  -0.793   1.916  1.00  0.00           H  
HETATM   57  H   UNL     1       1.681   0.232   1.952  1.00  0.00           H  
HETATM   58  H   UNL     1       1.548  -1.485   1.504  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3   11   18                                       
CONECT    3    2    4   32   33                                       
CONECT    4    3    5   34   35                                       
CONECT    5    4    6    7   11                                       
CONECT    6    5   36                                                 
CONECT    7    5    8    8    9                                       
CONECT    8    7    7                                                 
CONECT    9    7   10   37   38                                       
CONECT   10    9   39                                                 
CONECT   11    5    2   12   13                                       
CONECT   12   11   40   41   42                                       
CONECT   13   11   14   43   44                                       
CONECT   14   13   15   15   16                                       
CONECT   15   14   14                                                 
CONECT   16   14   17   18   30                                       
CONECT   17   16                                                      
CONECT   18   16    2   19   20                                       
CONECT   19   18                                                      
CONECT   20   18   21   45   46                                       
CONECT   21   20   22   47   48                                       
CONECT   22   21   23   24   30                                       
CONECT   23   22                                                      
CONECT   24   22   25   49   50                                       
CONECT   25   24   26   27   28                                       
CONECT   26   25                                                      
CONECT   27   25   51                                                 
CONECT   28   25   29   52   53                                       
CONECT   29   28   30   54   55                                       
CONECT   30   29   16   22   31                                       
CONECT   31   30   56   57   58                                       
CONECT   32    3                                                      
CONECT   33    3                                                      
CONECT   34    4                                                      
CONECT   35    4                                                      
CONECT   36    6                                                      
CONECT   37    9                                                      
CONECT   38    9                                                      
CONECT   39   10                                                      
CONECT   40   12                                                      
CONECT   41   12                                                      
CONECT   42   12                                                      
CONECT   43   13                                                      
CONECT   44   13                                                      
CONECT   45   20                                                      
CONECT   46   20                                                      
CONECT   47   21                                                      
CONECT   48   21                                                      
CONECT   49   24                                                      
CONECT   50   24                                                      
CONECT   51   27                                                      
CONECT   52   28                                                      
CONECT   53   28                                                      
CONECT   54   29                                                      
CONECT   55   29                                                      
CONECT   56   31                                                      
CONECT   57   31                                                      
CONECT   58   31                                                      
MASTER        0    0    0    0    0    0    0    0   58    0   58    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:57})
 58 61  0  0  0  0  0  0  0  0999 V2000
   -0.9519    1.4982   -1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    1.3568   -0.5536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8813    2.4561    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260    2.0213   -0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754    0.4931   -0.5270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5966    0.1965   -1.8875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2312   -0.2132    0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    0.3015    1.4443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884   -1.5617    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6636   -2.0209    1.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8378    0.0796   -0.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6986   -0.2552    1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -1.0575   -1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -1.1907   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6545   -2.2685   -0.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556    0.0405   -0.7073 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.3540   -1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3644    1.1932    0.0423 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2586    0.9314    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2229    2.4488   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872    2.1872    0.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.0107   -0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4373    1.2526   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6236    0.7389    0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3204   -0.4243   -0.1748 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4812   -0.1676   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5793   -0.6785    0.4519 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -1.6754   -0.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950   -1.4032   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950   -0.2293   -0.0270 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1738   -0.5952    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7465    2.4776    1.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6496    3.4271   -0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    2.2476    0.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534    2.5323   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853    0.4720   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3420   -1.4775   -0.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9701   -2.2709   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0597   -2.8854    0.8785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699   -1.0760    1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.5485    1.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9563    0.6208    1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8123   -1.9836   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3930   -0.8219   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    2.6877   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333    3.2816    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2092    3.0772    0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489    1.9558    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478    1.6301    0.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4629    0.4824    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0774   -1.4052    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403   -2.5031   -0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2860   -1.9336    0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2532   -1.1449   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -2.2948   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1352   -0.7933    1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808    0.2322    1.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -1.4853    1.5045 H   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
  2 11  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4  5  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 36  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 13 14  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 30  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 22  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 30  1  0  0  0  0
 24 25  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 27 51  1  0  0  0  0
 28 29  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 29 30  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
 30 31  1  1  0  0  0
 31 56  1  0  0  0  0
 31 57  1  0  0  0  0
 31 58  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3a,5b)-3,17,21-Trihydroxy-pregnane-11,20-dione	HMDB
3,17-Dihydroxy-17-hydroxyacetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-one	HMDB
3a,17,21-Trihydroxy-5a-pregnane-11,20-dione	HMDB
3a,17,21-Trihydroxy-5b-pregnane-11,20-dione	HMDB
3alpha,17,21-Trihydroxy-5beta-pregnane-11,20-dione	HMDB
3alpha,17,21-Trihydroxypregnane-11,20-dione	HMDB
3b,17,21-Trihydroxy-5a-pregnane-11,20-dione	HMDB
5a-Pregnan-3b,17a,21-triol-11,20-dion	HMDB
Ba 2681	HMDB
tetrahydro e	HMDB
tetrahydro-Cortisone	HMDB
Tetrahydrocompound e	HMDB
Tetrahydrocortison	HMDB
Urocortisone	HMDB

Chemical Formula

C₂₁H₃₂O₅

Average Molecular Weight

364.4758

Monoisotopic Molecular Weight

364.224974134

IUPAC Name

(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one

Traditional Name

(1S,2S,5S,7S,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one

CAS Registry Number

53-05-4

SMILES

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

InChI Identifier

InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14-,15-,18+,19-,20-,21-/m0/s1

InChI Key

SYGWGHVTLUBCEM-SDYDLROXSA-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

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-hydroxysteroid
11-oxosteroid
Oxosteroid
3-beta-hydroxysteroid
17-hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Anorexia nervosa

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Industrial application:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.68 m³·mol⁻¹	ChemAxon
Polarizability	40.47 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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	186.429	31661259
DarkChem	[M-H]-	Predicted	Not Available	183.235	31661259
AllCCS	[M+H]+	Predicted	Not Available	189.282	32859911
AllCCS	[M-H]-	Predicted	Not Available	192.984	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Tetrahydrocortisone,1TMS,#1	3299.8503	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TMS,#2	3253.5046	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TMS,#3	3254.9731	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TMS,#4	3092.8904	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TMS,#5	3207.65	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TMS,#6	3129.1199	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#1	3248.009	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#2	3304.6533	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#3	3073.6313	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#4	3104.887	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#5	3234.9788	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#6	3229.8745	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#7	3069.2405	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#8	3071.5085	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#9	3208.1785	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#10	3061.4856	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#11	3054.8967	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#12	3173.9321	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#13	2988.746	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TMS,#14	3022.062	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#1	3266.8213	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#2	3077.8105	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#3	3068.368	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#4	3195.6462	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#5	3082.5671	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#6	3102.4734	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#7	3243.74	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#8	3005.4426	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#9	3032.9841	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#10	3039.0823	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#11	3034.4258	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#12	3174.7346	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#13	2972.063	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#14	3004.4478	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#15	2973.1145	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TMS,#16	2971.4595	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#1	3536.7104	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#2	3537.4255	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#3	3497.6536	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#4	3341.8699	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#5	3450.5884	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,1TBDMS,#6	3369.2812	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#1	3799.4734	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#2	3717.2559	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#3	3530.325	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#4	3712.6013	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#5	3565.785	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#6	3722.2986	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#7	3529.0535	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#8	3676.455	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#9	3550.973	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#10	3514.394	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#11	3505.126	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#12	3647.939	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#13	3444.3425	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,2TBDMS,#14	3466.4456	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#1	3991.612	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#2	3748.8677	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#3	3943.3416	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#4	3785.9333	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#5	3725.4888	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#6	3715.668	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#7	3900.8755	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#8	3678.1243	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#9	3706.5234	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#10	3726.3047	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#11	3856.468	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#12	3695.514	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#13	3634.9282	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#14	3670.2788	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#15	3652.42	https://arxiv.org/abs/1905.12712
Tetrahydrocortisone,3TBDMS,#16	3632.3071	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bua-3329000000-2fc8cde1a6f7cbf833e0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1402490000-42e5bdb758e6ab7df7db	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-002b-0019000000-d250ba5babf82eddad0e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-002b-1960000000-f9b927b045d86760eeb6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4l-4900000000-2464c3721a88f6a054fc	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-0009000000-9c872091c11d421f014c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p1-0049000000-af1ad9a1ea8db1d650d4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052s-1192000000-21755048697813c79a2b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-784e6ec242f4642ea5b8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bta-2029000000-9f2c95a66681e65408bb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9076000000-8477ed7e9c8d0c2c4587	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-ff01cf842eca94c822cd	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0159-1019000000-c7d6aa4cd8a49fe9f1f5	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2059000000-d99165eb37d6b524d3cb	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mk-0009000000-a2a3efef8833bc2ae58c	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0901000000-ed28984735cfd01a3dae	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0295-8790000000-3224d1d7d418505226c6	2021-09-08	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD₃OD, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Urine	Detected and Quantified	0.40 +/- 0.44 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	18545203	details
Urine	Detected and Quantified	0.41 (0.38-0.49) umol/mmol creatinine	Adult (>18 years old)	Male	Normal	11085621	details
Urine	Detected and Quantified	0.32 +/- 0.37 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	18545203	details
Urine	Detected and Quantified	0.51 +/- 0.067 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15560936	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.023 +/- 0.009 uM	Adult (>18 years old)	Both	Anorexia nervosa	2165347	details
Urine	Detected and Quantified	0.40 +/- 0.052 umol/mmol creatinine	Adult (>18 years old)	Female	Eating disorder	15560936	details
Urine	Detected and Quantified	1.5 +/- 0.53 umol/mmol creatinine	Adult (>18 years old)	Female	Eating disorder	15560936	details

Associated Disorders and Diseases

Disease References

Anorexia nervosa
Vierhapper H, Kiss A, Nowotny P, Wiesnagrotzki S, Monder C, Waldhausl W: Metabolism of cortisol in anorexia nervosa. Acta Endocrinol (Copenh). 1990 Jun;122(6):753-8. [PubMed:2165347 ]

Associated OMIM IDs

606788 (Anorexia nervosa)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022310

KNApSAcK ID

Not Available

Chemspider ID

16735652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrahydrocortisone

METLIN ID

1915

PubChem Compound

12444617

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Baggett, Billy; Kinsella, Ralph A., Jr.; Doisy, Edward A. Hydrolysis of conjugates of urinary corticoids with b-glucuronidase. II. The isolation and determination of tetrahydrocortisone. Journal of Biological Chemistry (1953), 203 1013-22.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mune T, White PC: Apparent mineralocorticoid excess: genotype is correlated with biochemical phenotype. Hypertension. 1996 Jun;27(6):1193-9. [PubMed:8641723 ]
Weykamp CW, Penders TJ, Schmidt NA, Borburgh AJ, van de Calseyde JF, Wolthers BJ: Steroid profile for urine: reference values. Clin Chem. 1989 Dec;35(12):2281-4. [PubMed:2591044 ]
Koren W, Grienspuhn A, Kuznetsov SR, Berezin M, Rosenthal T, Postnov YV: Enhanced Na+/H+ exchange in Cushing's syndrome reflects functional hypermineralocorticoidism. J Hypertens. 1998 Aug;16(8):1187-91. [PubMed:9794723 ]
Rosler A, Leiberman E, Rosenmann A, Ben-Uzilio R, Weidenfeld J: Prenatal diagnosis of 11beta-hydroxylase deficiency congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1979 Oct;49(4):546-51. [PubMed:314453 ]
Stiefel P, Garcia-Morillo JS, Jimenez L, Pamies E, Miranda ML, Carneado J, Villar J, Leal-Cerro A: Role of ketoconazole treatment in urinary-free cortisol-to-cortisone and tetrahydrocortisol-to-tetrahydrocortisone ratios in nonectopic Cushing's syndrome. Endocrine. 2002 Aug;18(3):279-84. [PubMed:12450320 ]
Wallace AM, Banfield E, Ingram M, Fraser R, Swan L, Hillis WS, Connell JM: Glucocorticoids contribute to the heritability of leptin in Scottish adult female twins. Clin Endocrinol (Oxf). 2004 Jul;61(1):149-54. [PubMed:15212658 ]
Malunowicz EM, Romer TE, Urban M, Bossowski A: 11beta-hydroxysteroid dehydrogenase type 1 deficiency ('apparent cortisone reductase deficiency') in a 6-year-old boy. Horm Res. 2003;59(4):205-10. [PubMed:12649576 ]
Melander O, Frandsen E, Groop L, Hulthen UL: No evidence of a relation between 11beta-hydroxysteroid dehydrogenase type 2 activity and salt sensitivity. Am J Hypertens. 2003 Sep;16(9 Pt 1):729-33. [PubMed:12944030 ]
Vierhapper H, Nowotny P, Waldhausl W: Urinary steroid excretion rates in acromegaly. Horm Res. 2005;63(5):234-7. Epub 2005 May 17. [PubMed:15900108 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

Tetrahydrocortisone + NAD → 17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Ion	details
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + Hydrogen Ion + NADPH → Tetrahydrocortisone + NADP	details

Showing metabocard for Tetrahydrocortisone (HMDB0000903)

MOL for HMDB0000903 (Tetrahydrocortisone)

3D MOL for HMDB0000903 (Tetrahydrocortisone)

3D SDF for HMDB0000903 (Tetrahydrocortisone)

3D-SDF for HMDB0000903 (Tetrahydrocortisone)

PDB for HMDB0000903 (Tetrahydrocortisone)

3D PDB for HMDB0000903 (Tetrahydrocortisone)

SMILES for HMDB0000903 (Tetrahydrocortisone)

INCHI for HMDB0000903 (Tetrahydrocortisone)

Structure for HMDB0000903 (Tetrahydrocortisone)

3D Structure for HMDB0000903 (Tetrahydrocortisone)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions