NP-MRD: Showing NP-Card for 18-Hydroxycorticosterone (NP0086547)

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Record Information

Version

2.0

Created at

2022-05-11 16:24:02 UTC

Updated at

2022-05-11 16:24:02 UTC

NP-MRD ID

NP0086547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-Hydroxycorticosterone

Description

18-Hydroxycorticosterone 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, 18-hydroxycorticosterone is considered to be a steroid lipid molecule. 18-Hydroxycorticosterone is a corticosteroid and a derivative of corticosterone. Chronically high levels of 18-hydroxycorticosterone are associated with at least three inborn errors of metabolism including adrenal hyperplasia type V, corticosterone methyl oxidase I deficiency, and corticosterone methyl oxidase II deficiency. It serves as an intermediate in the synthesis of aldosterone by the enzyme aldosterone synthase in the zona glomerulosa. This imbalance leads to low levels of sodium and high levels of potassium in the blood (hyponatremia and hyperkalemia, respectively). 18-Hydroxycorticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 18-hydroxycorticosterone participates in a number of enzymatic reactions. In particular, 18-hydroxycorticosterone can be converted into aldosterone; which is catalyzed by the enzyme cytochrome P450 11B2. In addition, 18-hydroxycorticosterone can be biosynthesized from corticosterone through the action of the enzyme cytochrome P450 11B1. In humans, 18-hydroxycorticosterone is involved in the metabolic disorder called the corticosterone methyl oxidase II deficiency (cmo II) pathway. 18-Hydroxycorticosterone is a potentially toxic compound. 18-Hydroxycorticosterone was first documented in 1981 (PMID: 7226574). In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy) (PMID: 12505784) (PMID: 22238407) (PMID: 6887870) (PMID: 2009228).

Structure

MOL 3D MOL SDF PDB SMILES InChI

18-Hydroxycorticosterone .mol
  Mrv1652302121822582D          

 29 32  0  0  0  0            999 V2000
   -2.6388   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533   -2.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9335   -0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7181   -0.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181    0.6661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9731    1.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4210    2.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7700    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533    1.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335    0.4112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0197    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190    0.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    0.4112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2099    0.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2099   -0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2099   -0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523    1.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -1.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -0.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335   -1.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  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  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 10 18  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
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 19 26  1  0  0  0  0
 23 27  1  6  0  0  0
  9 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    3.0697   -0.9300   -1.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    0.1243   -0.2764 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1692    1.4450   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6557    1.4358   -0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905    0.6545    0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5373    0.5844    0.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4137    0.0300    1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594   -0.2194    1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3630   -0.8744    2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1174   -0.0154    2.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3648   -0.2806    0.9273 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0972    0.2791   -0.2901 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4179   -0.3716   -1.4833 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6833   -1.7473   -1.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443   -0.0988   -1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -0.3362   -0.2772 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1499   -1.7589   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -2.3087   -1.0442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    0.6228   -0.0851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0634    0.4671   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0876   -0.2731   -1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2857    1.2968   -0.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2278    1.0244   -1.7433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2797    0.3435    1.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9207    0.0291    2.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875    0.2483    0.9002 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1900   -0.8054   -1.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435   -1.9593   -0.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895   -0.7939   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7830    2.2511   -0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7703    1.6398   -1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0116    1.0953   -1.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092    2.4848   -0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8499   -0.2335    2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0787   -1.8749    1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -0.8810    3.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4966   -0.3622    3.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    1.0682    2.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3911   -1.3795    0.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7827    1.3634   -0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8360    0.0139   -2.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7200   -2.1798   -2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919    0.9548   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4843   -0.7234   -2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7525   -1.8601    0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347   -2.3852    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134   -3.2796   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003    1.6417   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437    1.0418    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0349    2.3904   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1276    1.2940   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6906    1.2897    1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0237   -0.4300    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8993   -0.9374    2.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7284    0.8363    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462    1.3495    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 24  1  0
 24 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 19 16  1  0
 16 17  1  1
 17 18  1  0
 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  2  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 26  1  0
  2 12  1  0
 11 26  1  0
  2  8  1  0
 26 56  1  6
 25 54  1  0
 25 55  1  0
 24 52  1  0
 24 53  1  0
 19 48  1  1
 22 49  1  0
 22 50  1  0
 23 51  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 15 43  1  0
 15 44  1  0
 13 41  1  6
 14 42  1  0
 12 40  1  6
 11 39  1  6
 10 37  1  0
 10 38  1  0
  9 35  1  0
  9 36  1  0
  7 34  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

18-Hydroxycorticosterone .mol
  Mrv1652302121822582D          

 29 32  0  0  0  0            999 V2000
   -2.6388   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533   -2.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388   -0.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -0.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9244   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -1.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9335   -0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7181   -0.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2031   -0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181    0.6661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9731    1.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4210    2.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7700    1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533    1.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335    0.4112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0197    1.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190    0.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    0.4112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2099    0.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -0.4138    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2099   -0.8263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2099   -0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523    1.7166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -1.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -0.0013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335   -1.2388    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  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  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 10 18  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
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  1  0  0  0
 19 26  1  0  0  0  0
 23 27  1  6  0  0  0
  9 28  1  1  0  0  0
 10 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086547

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1

> <INCHI_KEY>
HFSXHZZDNDGLQN-ZVIOFETBSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.4599

> <EXACT_MASS>
362.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.76700665940721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
0.7418204010000004

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.715825962499885

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.799060379167592

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7672247982276605

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
97.7747

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-FEB-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 18-Hydroxycorticosterone .mol                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-FEB-18         0                                  
HETATM    1  C   UNK     0      -4.926  -3.082   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.259  -3.852   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.926  -1.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.592  -0.772   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.592  -3.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.258  -3.082   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.925  -3.852   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.409  -3.082   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.409  -1.542   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.743  -0.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.207  -1.248   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.112  -0.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.207   1.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.683   2.708   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.653   3.852   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.171   3.107   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.259   2.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.743   0.768   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.903   2.299   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.409   1.538   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.925   0.768   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.258   1.538   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.925  -0.772   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.258  -1.542   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.258  -0.002   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.658   3.204   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -0.925  -2.312   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.409  -0.002   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.743  -2.312   0.000  0.00  0.00           H+0
CONECT    1    2    3    5                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3   24                                                       
CONECT    5    1    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   23   28                                             
CONECT   10    9   11   18   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13   10   19   20                                             
CONECT   19   18   26                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    9   24   27                                             
CONECT   24   23    4    6   25                                             
CONECT   25   24                                                            
CONECT   26   19                                                            
CONECT   27   23                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
11b,18,21-Trihydroxy-pregn-4-ene-3,20-dione	HMDB
18 Hydrocorticosterone	HMDB
18 Hydroxycorticosterone	HMDB
18-Hydrocorticosterone	HMDB
Hydroxycorticosterone, 18	HMDB
(11Β)-11,18,21-trihydroxypregn-4-ene-3,20-dione	HMDB
(11beta)-11,18,21-Trihydroxypregn-4-ene-3,20-dione	HMDB

Chemical Formula

C₂₁H₃₀O₅

Average Mass

362.4599 Da

Monoisotopic Mass

362.20932 Da

IUPAC Name

(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H30O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,14-17,19,22-23,25H,2-7,9-11H2,1H3/t14-,15-,16+,17-,19+,20-,21+/m0/s1

InChI Key

HFSXHZZDNDGLQN-ZVIOFETBSA-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
Pregnane-skeleton
20-oxosteroid
18-hydroxysteroid
3-oxo-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:16485 )
11beta-hydroxy steroid (CHEBI:16485 )
20-oxo steroid (CHEBI:16485 )
21-hydroxy steroid (CHEBI:16485 )
18-hydroxy steroid (CHEBI:16485 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C01124 )
Mineralocorticoids (C01124 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030091 )

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	1.28	ALOGPS
logP	0.74	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.8	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	3	ChemAxon
Refractivity	97.77 m³·mol⁻¹	ChemAxon
Polarizability	39.77 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

HMDB0000319

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021945

KNApSAcK ID

Not Available

Chemspider ID

10748

KEGG Compound ID

C01124

BioCyc ID

18-HYDROXYCORTICOSTERONE

BiGG ID

Not Available

Wikipedia Link

18-Hydroxycorticosterone

METLIN ID

5308

PubChem Compound

11222

PDB ID

Not Available

ChEBI ID

16485

Good Scents ID

Not Available

References

General References

Shakerdi LA, Connell JM, Fraser R, Wallace AM: Analysis of biological samples by gas chromatography-mass spectrometry without a reference standard: measurement of urinary 18-hydroxytetrahydro-11-dehydrocorticosterone excretion rate in human subjects. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 5;784(2):367-73. doi: 10.1016/s1570-0232(02)00825-5. [PubMed:12505784 ]
Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, Rabbia F, Terzolo M, Gomez-Sanchez EP, Gomez-Sanchez CE, Veglio F: 18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes. J Clin Endocrinol Metab. 2012 Mar;97(3):881-9. doi: 10.1210/jc.2011-2384. Epub 2012 Jan 11. [PubMed:22238407 ]
Sonino N, Chow D, Levine LS, New MI: Clinical response to metyrapone as indicated by measurement of mineralocorticoids and glucocorticoids in normal children. Clin Endocrinol (Oxf). 1981 Jan;14(1):31-9. doi: 10.1111/j.1365-2265.1981.tb00362.x. [PubMed:7226574 ]
Vecsei P, Abdelhamid S, Mittelstadt GV, Lichtwald K, Haack D, Lewicka S: Aldosterone metabolites and possible aldosterone precursors in hypertension. J Steroid Biochem. 1983 Jul;19(1A):345-51. [PubMed:6887870 ]
Kooner JS, Few JD, Lee CY, Taylor GM, James VH: Investigation of the salivary 18-hydroxycorticosterone:aldosterone ratio in man using a direct assay. J Steroid Biochem Mol Biol. 1991 Mar;38(3):377-82. doi: 10.1016/0960-0760(91)90110-q. [PubMed:2009228 ]

Showing NP-Card for 18-Hydroxycorticosterone (NP0086547)

MOL for NP0086547 (18-Hydroxycorticosterone)

3D MOL for NP0086547 (18-Hydroxycorticosterone)

3D SDF for NP0086547 (18-Hydroxycorticosterone)

3D-SDF for NP0086547 (18-Hydroxycorticosterone)

PDB for NP0086547 (18-Hydroxycorticosterone)

3D PDB for NP0086547 (18-Hydroxycorticosterone)

SMILES for NP0086547 (18-Hydroxycorticosterone)

INCHI for NP0086547 (18-Hydroxycorticosterone)

Structure for NP0086547 (18-Hydroxycorticosterone)

3D Structure for NP0086547 (18-Hydroxycorticosterone)