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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:48:29 UTC

Update Date

2022-09-22 18:34:41 UTC

HMDB ID

HMDB0341225

Secondary Accession Numbers

None

Metabolite Identification

Common Name

17,20,21-Trihydroxypregn-1-ene-3,11-dione

Description

17,20,21-Trihydroxypregn-1-ene-3,11-dione 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. Based on a literature review a significant number of articles have been published on 17,20,21-Trihydroxypregn-1-ene-3,11-dione.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309092222262D          

 26 29  0  0  0  0            999 V2000
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2050    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007    0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -1.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  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
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  0  0  0  0
M  END

  Mrv1652309092222262D          

 26 29  0  0  0  0            999 V2000
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2050    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007    0.8575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -1.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9089   -0.9576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  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
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341225

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC(=O)C3C(CCC4CC(=O)C=CC34C)C1CCC2(O)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/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/h5,7,12,14-15,17-18,22,25-26H,3-4,6,8-11H2,1-2H3

> <INCHI_KEY>
YKQDRSAOXBPFTF-UHFFFAOYSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.466

> <EXACT_MASS>
362.209324066

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.696894718637125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-5,17-dione

> <JCHEM_LOGP>
1.0891623386666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.311681066086301

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.990163753398893

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9765358169143195

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
97.50809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.357  -0.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.583   0.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.388   1.601   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.552  -2.387   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.163  -1.787   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2   12   16                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17    7   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19    6   21   26                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19                                                       
CONECT   26   20                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₅

Average Molecular Weight

362.466

Monoisotopic Molecular Weight

362.209324066

IUPAC Name

14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-5,17-dione

Traditional Name

14-(1,2-dihydroxyethyl)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-5,17-dione

CAS Registry Number

Not Available

SMILES

CC12CC(=O)C3C(CCC4CC(=O)C=CC34C)C1CCC2(O)C(O)CO

InChI Identifier

InChI=1S/C21H30O5/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/h5,7,12,14-15,17-18,22,25-26H,3-4,6,8-11H2,1-2H3

InChI Key

YKQDRSAOXBPFTF-UHFFFAOYSA-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
Pregnane-skeleton
3-oxo-delta-1-steroid
3-oxosteroid
11-oxosteroid
Oxosteroid
17-hydroxysteroid
Delta-1-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Cyclic ketone
Primary alcohol
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.09	ChemAxon
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-3	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	97.51 m³·mol⁻¹	ChemAxon
Polarizability	39.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85681016

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for 17,20,21-Trihydroxypregn-1-ene-3,11-dione (HMDB0341225)

MOL for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

3D MOL for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

3D SDF for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

3D-SDF for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

PDB for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

3D PDB for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

SMILES for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

INCHI for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

Structure for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

3D Structure for HMDB0341225 (17,20,21-Trihydroxypregn-1-ene-3,11-dione)

Predicted Kovats Retention Indices