Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-06 16:16:43 UTC
Update Date2021-09-16 15:27:41 UTC
HMDB IDHMDB0006768
Secondary Accession Numbers
  • HMDB06768
Metabolite Identification
Common Name19-Oxoandrost-4-ene-3,17-dione
Description19-Oxoandrost-4-ene-3,17-dione 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. 19-Oxoandrost-4-ene-3,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752405
Synonyms
ValueSource
19-OxoandrostenedioneHMDB
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(2S,10R,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde
Traditional Name(2S,10R,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-2-carbaldehyde
CAS Registry NumberNot Available
SMILES
[H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O
InChI Identifier
InChI=1S/C19H24O3/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/h10-11,14-16H,2-9H2,1H3/t14-,15?,16?,18-,19+/m0/s1
InChI KeyXRCFMDPVHKVRDJ-NHMXRCTMSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 19-oxosteroid
  • 3-oxosteroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP10(2.59) g/LALOGPS
logP10(2.96) g/LChemAxon
logS10(-3.7) g/LALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.21 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.4 m³·mol⁻¹ChemAxon
Polarizability33.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.89731661259
DarkChem[M-H]-166.5331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
19-Oxoandrost-4-ene-3,17-dione[H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O3526.8Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione[H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O2717.9Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione[H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=O2812.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C2908.8Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C2543.1Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(=O)CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C3173.3Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #2C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CCC2=O2779.3Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #2C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CCC2=O2703.0Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TMS,isomer #2C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CCC2=O3279.7Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C2798.8Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C2715.9Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CCC3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C=O)C1CC=C2O[Si](C)(C)C3250.6Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2[C@@H]3CCC4=CC(=O)CC[C@]4(C=O)C3CC[C@]12C3160.7Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2[C@@H]3CCC4=CC(=O)CC[C@]4(C=O)C3CC[C@]12C2725.4Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC2[C@@H]3CCC4=CC(=O)CC[C@]4(C=O)C3CC[C@]12C3339.2Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CCC(=O)[C@@]3(C)CCC123033.9Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CCC(=O)[C@@]3(C)CCC122943.5Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CCC(=O)[C@@]3(C)CCC123444.7Standard polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123283.4Semi standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123057.3Standard non polar33892256
19-Oxoandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C=O)C(=C1)CC[C@H]1C3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CCC123485.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0290000000-3f3c07c2928d5eb6bc482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 10V, Positive-QTOFsplash10-0udi-0069000000-4cf0f82f29d435064aae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 20V, Positive-QTOFsplash10-0g59-0191000000-13cd084dbfd20757dd232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 40V, Positive-QTOFsplash10-0udi-4390000000-07c1a3f2313a8bcd74182017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 10V, Negative-QTOFsplash10-0002-0090000000-9682812a6c76b322e6142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 20V, Negative-QTOFsplash10-0002-0090000000-bcf61fd273859ebc35f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 40V, Negative-QTOFsplash10-00l6-1090000000-00fa9379a73ca4316f952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 10V, Positive-QTOFsplash10-0udi-0049000000-f42da796c6c42c1abdd72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 20V, Positive-QTOFsplash10-05fr-0290000000-ea9fb5e90b08fc41c2c12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 40V, Positive-QTOFsplash10-052b-1900000000-f1ce177a03ad82bc6f3c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 10V, Negative-QTOFsplash10-0002-0090000000-a118d42b688aa2d698022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 20V, Negative-QTOFsplash10-00dj-0090000000-d4f4516a60eaa4281c592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Oxoandrost-4-ene-3,17-dione 40V, Negative-QTOFsplash10-00xr-1790000000-403ad3c430383cc1e0932021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024070
KNApSAcK IDNot Available
Chemspider ID17465008
KEGG Compound IDC05297
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16399653
PDB IDNot Available
ChEBI ID1069535
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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

Enzymes

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