Boldione (CHEM035527)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:50:59 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035527
Identification
Common NameBoldione
ClassSmall Molecule
DescriptionA steroid that consists of androstane having double bonds at positions 1 and 4 and two keto groups at positions 3 and 17.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass284.393 g/mol
Monoisotopic Mass284.178 g/mol
CAS Registry Number897-06-3
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
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0590000000-6541a31ec672647c2513Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0920000000-c2ed6077391b4b85511aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-0096-7900000000-0e538c3554828587687dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dm-3900000000-5d42203f518a99185773Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dj-1900000000-19c879c287403c0ed2efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00dj-0910000000-004b73c2f16c9747052bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00y1-0960000000-9c049fde9edd83e377b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-000i-0090000000-59ad5b9288fa52be718cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-004l-5900000000-c06d7a1d1deabe2ff1f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-05dl-4900000000-fa822a5bff16e6c79e5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00di-2910000000-d9af7cc7fbe8d5314eb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-00di-1920000000-9967f8cfb367b47cc432Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-014i-0790000000-0d6677503a198b1035c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-APPI-QQ , positivesplash10-014i-0090000000-696830f2bd076fad3e71Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0910000000-f76cb8acbe3dda64f678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-97401279a4ed4f0109a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0390000000-086427ce5de936a67dfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbl-3490000000-d0da828aadfb92f0e18eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-3bf930b2450afcd9c7b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-45c4760674e826b36a01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fto-2190000000-493a7a2fafd41fe4def6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-88e0917a0373fe627050Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-f15eb753b2ac78e32ce9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kaj-0390000000-5831bde5b618b84ffa7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-07ee8f0bccd26372634cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0790000000-f0dab0651773a8d88ad7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07373
HMDB IDHMDB0003422
FooDB IDFDB023170
Phenol Explorer IDNot Available
KNApSAcK IDC00047005
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBoldione
Chemspider ID12893
ChEBI ID40799
PubChem Compound ID13472
Kegg Compound IDC20144
YMDB IDNot Available
ECMDB IDM2MDB005196
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10843575
2. Brzezowska, Ewa; Kowalski, Tadeusz. Method for obtaining androsta-1,4-diene-3,17-dione. Pol. (2007), 4pp.
3. 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.
4. 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.
5. 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.