NP-MRD: Showing NP-Card for Dihydrocortisol (NP0087040)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...Show more...

Record Information

Version

2.0

Created at

2022-05-11 16:38:11 UTC

Updated at

2022-05-11 16:38:11 UTC

NP-MRD ID

NP0087040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrocortisol

Description

Dihydrocortisol 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, dihydrocortisol is considered to be a steroid lipid molecule. Dihydrocortisol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, dihydrocortisol participates in a number of enzymatic reactions. In particular, dihydrocortisol can be converted into cortisol through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, dihydrocortisol can be biosynthesized from tetrahydrocortisol through its interaction with the enzyme aldo-keto reductase family 1 member C4. In humans, dihydrocortisol is involved in the metabolic disorder called the 11-beta-hydroxylase deficiency (cyp11b1) pathway. Dihydrocortisol was first documented in 1983 (PMID: 6821952). A 17alpha-hydroxy-C21-steroid that is cortisol in which the 4-5 double bond has undergone formal hydrogenation to give the corresponding 5beta- steroid (PMID: 10543414) (PMID: 11585134) (PMID: 29375009) (PMID: 3793407).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652303192016422D          

 30 33  0  0  0  0            999 V2000
10001.078110001.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938710001.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.940710000.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7988 9998.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.366610000.2021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.9679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9998.9679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9407 9997.7209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2275 9999.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5130 9999.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5130 9998.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2275 9998.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9395 9999.3743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9395 9998.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6540 9998.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3685 9998.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366410001.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651910000.6208    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6519 9999.7957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3664 9999.3833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.080910000.6207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0809 9999.7958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8655 9999.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.350410000.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510000.8757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.865510001.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910002.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.7007    0.0000 O   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11  4  2  0  0  0  0
 12 14  1  0  0  0  0
 14  8  1  1  0  0  0
  9 13  1  0  0  0  0
 13  3  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18  2  1  1  0  0  0
 19 13  1  0  0  0  0
 19  6  1  6  0  0  0
 16 20  1  0  0  0  0
 20  5  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22  7  1  6  0  0  0
 17 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -2.2581   -1.4053   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2094    0.2645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9019   -0.7083    1.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4382   -0.6862    1.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768    0.7490    1.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7489    1.1672    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8473    1.6406    0.6765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0928    0.8461   -0.4029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3099    1.8484   -1.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0353    1.3808   -1.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2677    0.3918   -0.9624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8832    0.3552    0.4479 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0110   -0.2413    1.4451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5932   -1.0210    2.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391   -1.1033    0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -0.6295   -0.3112 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6338   -1.5924   -1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1629    0.7239   -0.7400 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0020    1.0384   -1.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3480    0.3275   -1.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.1524   -0.2140 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3038    1.0317    0.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1927   -1.1134    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2809   -2.2054   -0.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1545   -0.8010    1.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0268    0.4527    1.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2380   -1.9488   -0.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2900   -1.0777   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -2.1391   -0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6760   -1.7868    1.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7010   -0.0452    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965   -1.1277    0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8648   -1.2321    2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3042    2.5453    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406    1.9554    1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964    0.3519   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757    2.1926   -2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1154    2.7700   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    2.2664   -1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2110    0.9728   -2.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3393   -0.6027   -1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258    1.4513    0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486    0.5693    2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721   -0.6354    3.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6980   -2.1268    0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766   -1.2292    1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -2.2508   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791   -2.2898   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3665   -1.1171   -2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3127    1.4160    0.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2550    2.1329   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    0.8412   -2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    0.9932   -1.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3472   -0.5466   -2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    0.9820    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734   -0.9921    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0647   -1.5334    2.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5381    1.1562    1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 21 16  1  0
 16 17  1  6
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  6
 16 18  1  0
  2 12  1  0
 11 18  1  0
  2  8  1  0
 18 50  1  1
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 22 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 15 45  1  0
 15 46  1  0
 13 43  1  1
 14 44  1  0
 12 42  1  1
 11 41  1  6
 10 39  1  0
 10 40  1  0
  9 37  1  0
  9 38  1  0
  8 36  1  6
  7 34  1  0
  7 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

  Mrv1652303192016422D          

 30 33  0  0  0  0            999 V2000
10001.078110001.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938710001.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.940710000.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7988 9998.1344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.366610000.2021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6533 9998.9679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.0781 9998.9679    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9407 9997.7209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2275 9999.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5130 9999.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5130 9998.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2275 9998.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9395 9999.3743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.9395 9998.5492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.6540 9998.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3685 9998.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366410001.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.651910000.6208    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.6519 9999.7957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3664 9999.3833    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.080910000.6207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.0809 9999.7958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8655 9999.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.350410000.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.865510000.8757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.865510001.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210001.2882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.579210002.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.149910002.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.294910001.7007    0.0000 O   0  0  0  0  0  0  0  0  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11  4  2  0  0  0  0
 12 14  1  0  0  0  0
 14  8  1  1  0  0  0
  9 13  1  0  0  0  0
 13  3  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18  2  1  1  0  0  0
 19 13  1  0  0  0  0
 19  6  1  6  0  0  0
 16 20  1  0  0  0  0
 20  5  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  6  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 20 22  1  0  0  0  0
 22  7  1  6  0  0  0
 17 21  1  0  0  0  0
 21  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0087040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
ACSFOIGNUQUIGE-AIPUTVCKSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.4758

> <EXACT_MASS>
364.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.09860734946175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
1.3210007696666675

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.86612825927211

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.584777493497679

> <JCHEM_PKA_STRONGEST_BASIC>
-2.842415800615454

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
96.57329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8668.6798669.377   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8664.6868668.603   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.6898667.044   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8660.6918663.184   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8667.3518667.044   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.0198664.740   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8668.6798664.740   0.000  0.00  0.00           H+0
HETATM    8  H   UNK     0    8664.6898662.412   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8663.3588666.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.0248665.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.0248663.959   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3588663.189   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6878665.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6878663.959   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8666.0218663.189   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.3558663.959   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3518668.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0178667.825   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.0178666.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3518665.515   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.6848667.825   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.6848666.285   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.1498665.809   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8671.0548667.055   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.1498668.301   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8670.1498669.841   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8671.4818669.071   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8671.4818670.611   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0    8668.8138670.611   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0    8672.8178669.841   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   18                                                            
CONECT    3   13                                                            
CONECT    4   11                                                            
CONECT    5   20                                                            
CONECT    6   19                                                            
CONECT    7   22                                                            
CONECT    8   14                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   14                                                       
CONECT   13   14    9    3   19                                             
CONECT   14   13   15   12    8                                             
CONECT   15   14   16                                                       
CONECT   16   15   20                                                       
CONECT   17   18   21                                                       
CONECT   18   17   19    2                                                  
CONECT   19   18   20   13    6                                             
CONECT   20   19   16    5   22                                             
CONECT   21   22   25   17    1                                             
CONECT   22   21   23   20    7                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   26   27   21   24                                             
CONECT   26   25   28   29                                                  
CONECT   27   25                                                            
CONECT   28   26   30                                                       
CONECT   29   26                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
5beta-Pregnane-11beta,17alpha,21-triol-3,20-dione	KEGG
5b-Pregnane-11b,17a,21-triol-3,20-dione	Generator
5β-Pregnane-11β,17α,21-triol-3,20-dione	Generator
5-beta-Dihydrocortisol	HMDB
(5beta,11beta)-11,17,21-Trihydroxypregnane-3,20-dione	ChEBI
11-beta,17,21-Trihydroxy-5-beta-pregnane-3,20-dione	ChEBI
(5b,11b)-11,17,21-Trihydroxypregnane-3,20-dione	Generator
(5β,11β)-11,17,21-Trihydroxypregnane-3,20-dione	Generator
11-b,17,21-Trihydroxy-5-b-pregnane-3,20-dione	Generator
11-β,17,21-Trihydroxy-5-β-pregnane-3,20-dione	Generator
11beta,17,21-Trihydroxy-5beta-pregnane-3,20-dione	HMDB
11beta,17alpha,21-Trihydroxy-5beta-pregnane-3,20-dione	HMDB
11β,17,21-Trihydroxy-5β-pregnane-3,20-dione	HMDB
11β,17α,21-Trihydroxy-5β-pregnane-3,20-dione	HMDB
5beta-Dihydrocortisol	HMDB
5β-Dihydrocortisol	HMDB
Dihydrocortisol	HMDB

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4758 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-16,18,22,24,26H,3-11H2,1-2H3/t12-,14+,15+,16+,18-,19+,20+,21+/m1/s1

InChI Key

ACSFOIGNUQUIGE-AIPUTVCKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
3-oxo-5-beta-steroid
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

21-hydroxy steroid (CHEBI:732 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030204 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.8	ALOGPS
logP	1.32	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-2.8	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	96.57 m³·mol⁻¹	ChemAxon
Polarizability	40.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023133

KNApSAcK ID

Not Available

Chemspider ID

144508

KEGG Compound ID

C05471

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5α-Dihydrocortisol

METLIN ID

3173

PubChem Compound

164838

PDB ID

Not Available

ChEBI ID

732

Good Scents ID

Not Available

References

General References

Heilmann P, Heide J, Hundertmark S, Schoneshofer M: Administration of glycyrrhetinic acid: significant correlation between serum levels and the cortisol/cortisone-ratio in serum and urine. Exp Clin Endocrinol Diabetes. 1999;107(6):370-8. doi: 10.1055/s-0029-1212128. [PubMed:10543414 ]
Rivero-Marabe JJ, Maynar-Marino JI, Garcia-de-Tiedra MP, Galan-Martin AM, Caballero-Loscos MJ, Maynar-Marino M: Determination of natural corticosteroids in urine samples from sportsmen. J Chromatogr B Biomed Sci Appl. 2001 Sep 15;761(1):77-84. doi: 10.1016/s0378-4347(01)00306-1. [PubMed:11585134 ]
Schoneshofer M, Weber B, Nigam S: Increased urinary excretion of free 20 alpha- and 20 beta-dihydrocortisol in a hypercortisolemic but hypocortisoluric patient with Cushing's disease. Clin Chem. 1983 Feb;29(2):385-9. [PubMed:6821952 ]
Kallubai M, Reddy SP, Dubey S, Ramachary DB, Subramanyam R: Spectroscopic evaluation of synthesized 5beta-dihydrocortisol and 5beta-dihydrocortisol acetate binding mechanism with human serum albumin and their role in anticancer activity. J Biomol Struct Dyn. 2019 Feb;37(3):623-640. doi: 10.1080/07391102.2018.1433554. Epub 2018 Feb 15. [PubMed:29375009 ]
Southren AL, Hernandez MR, l'Hommedieu D, Gordon GG, Weinstein BI: Potentiation of collagen synthesis in explants of the rabbit eye by 5 beta-dihydrocortisol. Invest Ophthalmol Vis Sci. 1986 Dec;27(12):1757-60. [PubMed:3793407 ]

Showing NP-Card for Dihydrocortisol (NP0087040)

MOL for NP0087040 (Dihydrocortisol)

3D MOL for NP0087040 (Dihydrocortisol)

3D SDF for NP0087040 (Dihydrocortisol)

3D-SDF for NP0087040 (Dihydrocortisol)

PDB for NP0087040 (Dihydrocortisol)

3D PDB for NP0087040 (Dihydrocortisol)

SMILES for NP0087040 (Dihydrocortisol)

INCHI for NP0087040 (Dihydrocortisol)

Structure for NP0087040 (Dihydrocortisol)

3D Structure for NP0087040 (Dihydrocortisol)