4-Dihydroboldenone (CHEM036023)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:44 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036023
Identification
Common Name4-Dihydroboldenone
ClassSmall Molecule
DescriptionA 3-oxo Delta(1)-steroid with 5beta-configuration formed from 17beta-hydroxyandrosta-1,4-dien-3-one by reduction across the C4-C5 double bond.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5beta,17beta)-17-Hydroxyandrost-1-en-3-oneChEBI
(5b,17b)-17-Hydroxyandrost-1-en-3-oneGenerator
(5Β,17β)-17-hydroxyandrost-1-en-3-oneGenerator
17b-Hydroxy-5b -androst-1-en-3-oneHMDB
17b-Hydroxy-5b-androst-1-en-3-oneHMDB, Generator
5b-Androst-1-en-17b-ol-3-oneHMDB
5b-Androst-1-ene-17b-ol-3-oneHMDB
5beta-Androst-1-en-17beta-ol-3-oneMeSH, HMDB
Androst-1-en-17-ol-3-oneMeSH, HMDB
17β-Hydroxy-5β-androst-1-en-3-oneGenerator
17beta-Hydroxy-5beta-androst-1-en-3-oneHMDB
4-DihydroboldenoneHMDB
5beta-Androst-1-ene-17beta-ol-3-oneHMDB
5β-Androst-1-en-17β-ol-3-oneHMDB
5β-Androst-1-ene-17β-ol-3-oneHMDB
Chemical FormulaC19H28O2
Average Molecular Mass288.424 g/mol
Monoisotopic Mass288.209 g/mol
CAS Registry Number10529-96-1
IUPAC Name(1S,2R,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-one
Traditional Name(1S,2R,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-en-5-one
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C19H28O2/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/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1
InChI KeyOKJCFMUGMSVJBG-MISPCMORSA-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
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 3-oxo-5-beta-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • 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 Solubility0.013 g/LALOGPS
logP3.38ALOGPS
logP3.41ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.7 m³·mol⁻¹ChemAxon
Polarizability33.61 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, Positivesplash10-05i9-0490000000-f6ebedc0daa2295b81c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000t-1219000000-33752dbf36217e013441Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-16a979e47d20a140bb20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022i-0290000000-1903847e4640d27ffe3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002o-3890000000-365296df3fe861648302Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-507160a36d5fc98fe109Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c58084752b6f0048e230Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-1090000000-79ab60776a39e76e2172Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-b2999bc7d49ce2a4db44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0960000000-1321f449097600ca5668Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-7da59599892bb5ce25b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0090000000-50477ff83a0e087a0650Spectrum
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 IDNot Available
HMDB IDHMDB0006035
FooDB IDFDB023811
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20045328
ChEBI ID87331
PubChem Compound ID12133279
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19089863
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21255593
3. Masse R, Ayotte C, Dugal R: Studies on anabolic steroids. I. Integrated methodological approach to the gas chromatographic-mass spectrometric analysis of anabolic steroid metabolites in urine. J Chromatogr. 1989 Apr 7;489(1):23-50.
4. Maughan RJ: Contamination of dietary supplements and positive drug tests in sport. J Sports Sci. 2005 Sep;23(9):883-9.
5. Fineschi V, Riezzo I, Centini F, Silingardi E, Licata M, Beduschi G, Karch SB: Sudden cardiac death during anabolic steroid abuse: morphologic and toxicologic findings in two fatal cases of bodybuilders. Int J Legal Med. 2007 Jan;121(1):48-53. Epub 2005 Nov 15.
6. VanHelder WP, Kofman E, Tremblay MS: Anabolic steroids in sport. Can J Sport Sci. 1991 Dec;16(4):248-57.
7. Saudan C, Baume N, Robinson N, Avois L, Mangin P, Saugy M: Testosterone and doping control. Br J Sports Med. 2006 Jul;40 Suppl 1:i21-4.
8. Thevis M, Schanzer W: Mass spectrometry in sports drug testing: Structure characterization and analytical assays. Mass Spectrom Rev. 2007 Jan-Feb;26(1):79-107.
9. Green GA: Doping control for the team physician: a review of drug testing procedures in sport. Am J Sports Med. 2006 Oct;34(10):1690-8. Epub 2006 Aug 21.
10. Iversen P: Combined androgen blockade in the treatment of advanced prostate cancer--an overview. The Scandinavian Prostatic Cancer Group. Scand J Urol Nephrol. 1997 Jun;31(3):249-54.