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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:47:21 UTC

Update Date

2022-09-22 18:34:41 UTC

HMDB ID

HMDB0341222

Secondary Accession Numbers

None

Metabolite Identification

Common Name

11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one

Description

11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one 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 very few articles have been published on 11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309092222252D          

 31 34  0  0  1  0            999 V2000
    1.4440   -2.7799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -2.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9122   -2.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1278   -3.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7050   -2.3711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7974   -1.4499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9565   -3.7777    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  2  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

  Mrv1652309092222252D          

 31 34  0  0  1  0            999 V2000
    1.4440   -2.7799    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2561   -2.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9758   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9122   -2.1492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1278   -3.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7050   -2.3711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7974   -1.4499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9565   -3.7777    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  2  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 30  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0341222

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](O)(CO)[C@@]1(O)CC[C@@]2([H])[C@@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[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/h9,14-18,22,24-26H,3-8,10-11H2,1-2H3/t14-,15+,16+,17-,18-,19+,20+,21+/m1/s1

> <INCHI_KEY>
AWWCEQOCFFQUKS-ZENBKHFWSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
40.6074040128202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.6599902603333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.221821222821635

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.989630422523696

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8465845871140836

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
98.1667

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <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  H   UNK     0       2.696  -5.189   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       4.211  -4.918   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.688  -6.367   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.219  -3.741   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.703  -4.012   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.839  -6.183   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       8.783  -4.426   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       8.313  -1.800   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      10.822  -2.707   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       9.252  -7.052   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8   30                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   30                                             
CONECT   11   10                                                            
CONECT   12   10   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   12   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29    6   10   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11b,17a,20b,21-Tetrahydroxypregn-4-en-3-one	Generator
11Β,17α,20β,21-tetrahydroxypregn-4-en-3-one	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Molecular Weight

364.482

Monoisotopic Molecular Weight

364.22497413

IUPAC Name

(1S,2R,10R,11S,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CO)[C@@]1(O)CC[C@@]2([H])[C@@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[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/h9,14-18,22,24-26H,3-8,10-11H2,1-2H3/t14-,15+,16+,17-,18-,19+,20+,21+/m1/s1

InChI Key

AWWCEQOCFFQUKS-ZENBKHFWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

21-hydroxysteroid
Progestogin-skeleton
Pregnane-skeleton
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.66	ChemAxon
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.17 m³·mol⁻¹	ChemAxon
Polarizability	40.61 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

67153081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13367707

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 11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one (HMDB0341222)

MOL for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

3D MOL for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

3D SDF for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

3D-SDF for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

PDB for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

3D PDB for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

SMILES for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

INCHI for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

Structure for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

3D Structure for HMDB0341222 (11beta,17alpha,20beta,21-Tetrahydroxypregn-4-en-3-one)

Predicted Kovats Retention Indices