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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (24) Show 24 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 08:03:18 UTC

Update Date

2021-09-14 15:41:25 UTC

HMDB ID

HMDB0003955

Secondary Accession Numbers

HMDB03955

Metabolite Identification

Common Name

19-Hydroxyandrost-4-ene-3,17-dione

Description

19-Hydroxyandrost-4-ene-3,17-dione, also known as 19-HAED, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, 19-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid lipid molecule. 19-Hydroxyandrost-4-ene-3,17-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB03955.mol
  Mrv0541 02231219502D          

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 12 22  1  1  0  0  0
 10 23  1  6  0  0  0
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 20 25  1  0  0  0  0
M  END

HMDB03955.mol
  Mrv0541 02231219502D          

 25 28  0  0  0  0            999 V2000
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0797   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 10  5  1  0  0  0  0
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 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
 17 19  2  0  0  0  0
  5 20  1  1  0  0  0
  9 21  1  1  0  0  0
 12 22  1  1  0  0  0
 10 23  1  6  0  0  0
 11 24  1  6  0  0  0
 20 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003955

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1

> <INCHI_KEY>
XGUHPTGEXRHMQQ-BGJMDTOESA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.95371598701328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,10R,11S,15S)-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.6481798466666664

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.18419939480066

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.709452416108206

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9685930407626059

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
85.38219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
19-haed

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CCC(=O)%5BC@@...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:47})
 48 51  0  0  0  0  0  0  0  0999 V2000
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 25 48  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03955.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.151   0.467   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       2.977   2.871   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0      -2.211   1.100   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   20                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    9    5   14   23                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18    2                                                            
CONECT   19   17                                                            
CONECT   20    5   25                                                       
CONECT   21    9                                                            
CONECT   22   12                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CCC(=O)%5BC@@... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -2.002   0.687  -1.645  1.00  0.00           H  
HETATM    2  C   UNL     1      -2.070   0.740  -0.558  1.00  0.00           C  
HETATM    3  C   UNL     1      -3.077   1.816  -0.133  1.00  0.00           C  
HETATM    4  C   UNL     1      -4.442   1.123  -0.396  1.00  0.00           C  
HETATM    5  C   UNL     1      -4.183  -0.379  -0.361  1.00  0.00           C  
HETATM    6  O   UNL     1      -4.977  -1.260  -0.587  1.00  0.00           O  
HETATM    7  C   UNL     1      -2.739  -0.540   0.012  1.00  0.00           C  
HETATM    8  C   UNL     1      -2.599  -0.558   1.536  1.00  0.00           C  
HETATM    9  C   UNL     1      -2.007  -1.731  -0.574  1.00  0.00           C  
HETATM   10  C   UNL     1      -0.565  -1.685  -0.043  1.00  0.00           C  
HETATM   11  C   UNL     1       0.124  -0.371  -0.396  1.00  0.00           C  
HETATM   12  H   UNL     1       0.245  -0.308  -1.478  1.00  0.00           H  
HETATM   13  C   UNL     1      -0.686   0.858   0.056  1.00  0.00           C  
HETATM   14  H   UNL     1      -0.790   0.850   1.141  1.00  0.00           H  
HETATM   15  C   UNL     1       0.015   2.139  -0.396  1.00  0.00           C  
HETATM   16  C   UNL     1       1.388   2.251   0.277  1.00  0.00           C  
HETATM   17  C   UNL     1       2.159   0.980  -0.036  1.00  0.00           C  
HETATM   18  C   UNL     1       3.371   1.079  -0.575  1.00  0.00           C  
HETATM   19  C   UNL     1       4.102  -0.149  -0.918  1.00  0.00           C  
HETATM   20  O   UNL     1       5.313  -0.180  -0.978  1.00  0.00           O  
HETATM   21  C   UNL     1       3.252  -1.375  -1.192  1.00  0.00           C  
HETATM   22  C   UNL     1       2.309  -1.559  -0.003  1.00  0.00           C  
HETATM   23  C   UNL     1       1.499  -0.318   0.270  1.00  0.00           C  
HETATM   24  C   UNL     1       1.232  -0.290   1.776  1.00  0.00           C  
HETATM   25  O   UNL     1       2.476  -0.251   2.479  1.00  0.00           O  
HETATM   26  H   UNL     1      -2.963   2.057   0.924  1.00  0.00           H  
HETATM   27  H   UNL     1      -2.971   2.710  -0.748  1.00  0.00           H  
HETATM   28  H   UNL     1      -5.155   1.397   0.381  1.00  0.00           H  
HETATM   29  H   UNL     1      -4.825   1.413  -1.375  1.00  0.00           H  
HETATM   30  H   UNL     1      -3.151  -1.406   1.941  1.00  0.00           H  
HETATM   31  H   UNL     1      -1.546  -0.648   1.803  1.00  0.00           H  
HETATM   32  H   UNL     1      -3.001   0.368   1.948  1.00  0.00           H  
HETATM   33  H   UNL     1      -2.490  -2.655  -0.259  1.00  0.00           H  
HETATM   34  H   UNL     1      -2.003  -1.665  -1.662  1.00  0.00           H  
HETATM   35  H   UNL     1      -0.582  -1.798   1.041  1.00  0.00           H  
HETATM   36  H   UNL     1       0.000  -2.510  -0.476  1.00  0.00           H  
HETATM   37  H   UNL     1       0.143   2.118  -1.478  1.00  0.00           H  
HETATM   38  H   UNL     1      -0.594   3.001  -0.122  1.00  0.00           H  
HETATM   39  H   UNL     1       1.923   3.115  -0.117  1.00  0.00           H  
HETATM   40  H   UNL     1       1.264   2.352   1.355  1.00  0.00           H  
HETATM   41  H   UNL     1       3.811   2.048  -0.759  1.00  0.00           H  
HETATM   42  H   UNL     1       2.673  -1.228  -2.103  1.00  0.00           H  
HETATM   43  H   UNL     1       3.890  -2.252  -1.296  1.00  0.00           H  
HETATM   44  H   UNL     1       1.633  -2.388  -0.213  1.00  0.00           H  
HETATM   45  H   UNL     1       2.898  -1.803   0.881  1.00  0.00           H  
HETATM   46  H   UNL     1       0.646   0.594   2.025  1.00  0.00           H  
HETATM   47  H   UNL     1       0.680  -1.185   2.064  1.00  0.00           H  
HETATM   48  H   UNL     1       2.383  -0.232   3.442  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3    7   13                                       
CONECT    3    2    4   26   27                                       
CONECT    4    3    5   28   29                                       
CONECT    5    4    6    6    7                                       
CONECT    6    5    5                                                 
CONECT    7    5    2    8    9                                       
CONECT    8    7   30   31   32                                       
CONECT    9    7   10   33   34                                       
CONECT   10    9   11   35   36                                       
CONECT   11   10   12   13   23                                       
CONECT   12   11                                                      
CONECT   13   11    2   14   15                                       
CONECT   14   13                                                      
CONECT   15   13   16   37   38                                       
CONECT   16   15   17   39   40                                       
CONECT   17   16   18   18   23                                       
CONECT   18   17   17   19   41                                       
CONECT   19   18   20   20   21                                       
CONECT   20   19   19                                                 
CONECT   21   19   22   42   43                                       
CONECT   22   21   23   44   45                                       
CONECT   23   22   11   17   24                                       
CONECT   24   23   25   46   47                                       
CONECT   25   24   48                                                 
CONECT   26    3                                                      
CONECT   27    3                                                      
CONECT   28    4                                                      
CONECT   29    4                                                      
CONECT   30    8                                                      
CONECT   31    8                                                      
CONECT   32    8                                                      
CONECT   33    9                                                      
CONECT   34    9                                                      
CONECT   35   10                                                      
CONECT   36   10                                                      
CONECT   37   15                                                      
CONECT   38   15                                                      
CONECT   39   16                                                      
CONECT   40   16                                                      
CONECT   41   18                                                      
CONECT   42   21                                                      
CONECT   43   21                                                      
CONECT   44   22                                                      
CONECT   45   22                                                      
CONECT   46   24                                                      
CONECT   47   24                                                      
CONECT   48   25                                                      
MASTER        0    0    0    0    0    0    0    0   48    0   48    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CCC(=O)%5BC@@...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:47})
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
19-Hydroxyandrostenedione	ChEBI
19-Hydroxy-4-androstene-3,17-dione	HMDB
19-Hydroxy-4-androstene-3,17-dione, 18O-labeled	HMDB
19-HAED	HMDB

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

(1S,2S,10R,11S,15S)-2-(hydroxymethyl)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

Traditional Name

19-haed

CAS Registry Number

510-64-5

SMILES

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

InChI Identifier

InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1

InChI Key

XGUHPTGEXRHMQQ-BGJMDTOESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
19-hydroxysteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Primary alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:27576 )
19-hydroxy steroid (CHEBI:27576 )
17-oxo steroid (CHEBI:27576 )
androstanoid (CHEBI:27576 )
C19 steroids (androgens) and derivatives (C05290 )
C19 steroids (androgens) and derivatives (LMST02020067 )

Ontology

Physiological effect

Health effect:

Health condition:

Cushing's syndrome

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Organ and components:

Testicle

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

System process:

Reproduction

Cellular process:

Cell signaling

Industrial application:

Physical Properties

State

Solid

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

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.072 g/L	ALOGPS
logP	2.1	ALOGPS
logP	2.65	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	18.71	ChemAxon
pKa (Strongest Basic)	-0.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.38 m³·mol⁻¹	ChemAxon
Polarizability	33.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	171.897	31661259
DarkChem	[M-H]-	Predicted	Not Available	164.649	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
19-Hydroxyandrost-4-ene-3,17-dione,1TMS,#1	2874.7502	https://arxiv.org/abs/1905.12712
19-Hydroxyandrost-4-ene-3,17-dione,1TMS,#2	2901.6304	https://arxiv.org/abs/1905.12712
19-Hydroxyandrost-4-ene-3,17-dione,1TMS,#3	2818.3936	https://arxiv.org/abs/1905.12712
19-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,#1	3127.5457	https://arxiv.org/abs/1905.12712
19-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,#2	3156.875	https://arxiv.org/abs/1905.12712
19-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,#3	3090.8154	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0ufu-4910000000-ca91f3850d2822c36110	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0ufu-4910000000-acb494bbf38c6f0ab6ae	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)	splash10-0zi3-3920000000-2fb97be8369cef8834c8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)	splash10-0ug0-3920000000-088095d0d94653a7ded1	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufu-4910000000-ca91f3850d2822c36110	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ufu-4910000000-acb494bbf38c6f0ab6ae	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0zi3-3920000000-2fb97be8369cef8834c8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ug0-3920000000-088095d0d94653a7ded1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052o-2920000000-719a80545e9031debcba	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000f-3920000000-25496932221b91188e02	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-0290000000-4f45d95c38d59fa1da5e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00r2-1239000000-c5d6f655f6699da8120c	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0095000000-0c098e2b64d478a5e4d2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fri-0190000000-d6d70ed69da9f27bee29	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kdl-3490000000-5a0e988988f81f967b03	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0049000000-3a6715be3231f63279bb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ul0-0095000000-032bf9cb6539d3f7479a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1090000000-16932bcbf046cb12b8b5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-a31baae7fa83b1a9cb20	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0l2r-0291000000-86360d0dc940679c31bc	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05be-1900000000-8071003485ecbea19dce	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-80caba83ca693b662223	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-47ffb3556f0d805c33a6	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-1390000000-6e12d642905fa15bfaf5	2021-09-06	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Placenta
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Androstenedione Metabolism		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000323 +/- 0.000193 uM	Adult (>18 years old)	Both	Cushing's syndrome	8384536	details
Blood	Detected and Quantified	0.000092 +/- 0.000024 uM	Adult (>18 years old)	Both	Cushing's syndrome	8384536	details

Associated Disorders and Diseases

Disease References

Cushing's Syndrome
Mune T, Morita H, Yasuda K, Murayama M, Yamakita N, Miura K: Elevated plasma 19-hydroxyandrostenedione levels in Cushing's disease: stimulation with ACTH and inhibition with metyrapone. Clin Endocrinol (Oxf). 1993 Mar;38(3):265-72. [PubMed:8384536 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030282

KNApSAcK ID

Not Available

Chemspider ID

221136

KEGG Compound ID

C05290

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6990

PubChem Compound

252379

PDB ID

Not Available

ChEBI ID

27576

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Ueberwasser, H.; Heusler, K.; Kalvoda, J.; Meystre, Ch.; Wieland, P.; Anner, G.; Wettstein, A. Steroids. CXCIII. 19-Norsteroids. A simple route to 19-norandrostane derivatives. Helvetica Chimica Acta (1963), 46 344-52.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Osawa Y, Ohnishi S, Yarborough C, Ohigashi S, Kosaki T, Hashino M, Yanaihara T, Nakayama T: Serum level of 19-hydroxyandrostenedione during pregnancy and at delivery determined by gas chromatography/mass spectrometry. Steroids. 1990 Apr;55(4):165-9. [PubMed:2339447 ]
Padmanabhan V, Chappel SC, Beitins IZ: An improved in vitro bioassay for follicle-stimulating hormone (FSH): suitable for measurement of FSH in unextracted human serum. Endocrinology. 1987 Sep;121(3):1089-98. [PubMed:3113917 ]

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6. Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

7. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8. Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9. Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are 24 proteins in total.

Show all enzymes and transporters

Showing metabocard for 19-Hydroxyandrost-4-ene-3,17-dione (HMDB0003955)

MOL for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

3D MOL for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

3D SDF for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

3D-SDF for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

PDB for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

3D PDB for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

SMILES for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

INCHI for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

Structure for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

3D Structure for HMDB0003955 (19-Hydroxyandrost-4-ene-3,17-dione)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

Enzymes