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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 20:32:57 UTC
Update Date2021-09-14 15:41:24 UTC
HMDB IDHMDB0003422
Secondary Accession Numbers
  • HMDB03422
Metabolite Identification
Common NameBoldione
DescriptionBoldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054 , 16308875 , 16244993 ).
Structure
Data?1582752276
Synonyms
ValueSource
1,4-Androstadiene-3,17-dioneChEBI
1-DehydroandrostenedioneChEBI
ADDChEBI
ADTChEBI
AndrostadienedioneChEBI
Androst-1,4-diene-3,17-dioneMeSH
BoldioneChEBI
Androsta-1,4-diene-3, 17-dioneHMDB
Androsta-1,4-diene-3,17-dioneHMDB
Androstane-1,4-diene-3, 17-dioneHMDB
Androstra-1,4-diene-3,17-dioneHMDB
Chemical FormulaC19H24O2
Average Molecular Weight284.3927
Monoisotopic Molecular Weight284.177630012
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione
Traditional Nameandrosta-1,4-diene-3,17-dione
CAS Registry Number897-06-3
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeyLUJVUUWNAPIQQI-QAGGRKNESA-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
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP2.78ALOGPS
logP3.93ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.83ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.7 m³·mol⁻¹ChemAxon
Polarizability32.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available168.414http://allccs.zhulab.cn/database/detail?ID=AllCCS00001245
DarkChem[M+H]+PredictedNot Available169.30931661259
DarkChem[M-H]-PredictedNot Available162.16331661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0590000000-6541a31ec672647c25132017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0920000000-c2ed6077391b4b85511a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-0096-7900000000-0e538c3554828587687d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dm-3900000000-5d42203f518a991857732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dj-1900000000-19c879c287403c0ed2ef2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dj-0910000000-004b73c2f16c9747052b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00y1-0960000000-9c049fde9edd83e377b42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-000i-0090000000-59ad5b9288fa52be718c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-004l-5900000000-c06d7a1d1deabe2ff1f62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-05dl-4900000000-fa822a5bff16e6c79e5f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00di-2910000000-d9af7cc7fbe8d5314eb42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00di-1920000000-9967f8cfb367b47cc4322017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-014i-0790000000-0d6677503a198b1035c02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-014i-0090000000-696830f2bd076fad3e712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0910000000-f76cb8acbe3dda64f6782017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-97401279a4ed4f0109a42017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0390000000-086427ce5de936a67dfa2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbl-3490000000-d0da828aadfb92f0e18e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3bf930b2450afcd9c7b32017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-45c4760674e826b36a012017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fto-2190000000-493a7a2fafd41fe4def62017-07-26View 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 IDDB07373
Phenol Explorer Compound IDNot Available
FooDB IDFDB023170
KNApSAcK IDC00047005
Chemspider ID12893
KEGG Compound IDC20144
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBoldione
METLIN IDNot Available
PubChem Compound13472
PDB IDNot Available
ChEBI ID40799
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceBrzezowska, Ewa; Kowalski, Tadeusz. Method for obtaining androsta-1,4-diene-3,17-dione. Pol. (2007), 4pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pompa G, Arioli F, Fracchiolla ML, Rossi CA, Bassini AL, Stella S, Biondi PA: Neoformation of boldenone and related steroids in faeces of veal calves. Food Addit Contam. 2006 Feb;23(2):126-32. [PubMed:16449054 ]
  2. Kim Y, Jun M, Lee W: Characterization of boldione and its metabolites in human urine by liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(1):9-20. [PubMed:16308875 ]
  3. Arioli F, Chiesa LM, Fracchiolla ML, Biondi PA, Pompa G: ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results. Vet Res Commun. 2005 Aug;29 Suppl 2:355-7. [PubMed:16244993 ]