19-Hydroxyandrost-4-ene-3,17-dione (CHEM035605)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:55:19 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035605
Identification
Common Name19-Hydroxyandrost-4-ene-3,17-dione
ClassSmall Molecule
Description19-Hydroxyandrost-4-ene-3,17-dione, also known as 19-hydroxyandrost-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. 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. 19-Hydroxyandrost-4-ene-3,17-dione participates in a number of enzymatic reactions, within cattle. In particular, 19-Hydroxyandrost-4-ene-3,17-dione can be biosynthesized from androstenedione through its interaction with the enzyme cytochrome P450 19A1. In addition, 19-Hydroxyandrost-4-ene-3,17-dione can be converted into 19-oxoandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In cattle, 19-hydroxyandrost-4-ene-3,17-dione is involved in the metabolic pathway called the androstenedione metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
19-HydroxyandrostenedioneChEBI
19-Hydroxy-4-androstene-3,17-dioneHMDB
19-Hydroxy-4-androstene-3,17-dione, 18O-labeledHMDB
19-HAEDHMDB
Chemical FormulaC19H26O3
Average Molecular Mass302.408 g/mol
Monoisotopic Mass302.188 g/mol
CAS Registry Number510-64-5
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 Name19-haed
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO
InChI IdentifierInChI=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 KeyXGUHPTGEXRHMQQ-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.
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-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 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 Solubility0.072 g/LALOGPS
logP2.1ALOGPS
logP2.65ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)18.71ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.38 m³·mol⁻¹ChemAxon
Polarizability33.95 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufu-4910000000-ca91f3850d2822c36110Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufu-4910000000-acb494bbf38c6f0ab6aeSpectrum
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0zi3-3920000000-2fb97be8369cef8834c8Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0ug0-3920000000-088095d0d94653a7ded1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufu-4910000000-ca91f3850d2822c36110Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufu-4910000000-acb494bbf38c6f0ab6aeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zi3-3920000000-2fb97be8369cef8834c8Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-3920000000-088095d0d94653a7ded1Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052o-2920000000-719a80545e9031debcbaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000f-3920000000-25496932221b91188e02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0290000000-4f45d95c38d59fa1da5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r2-1239000000-c5d6f655f6699da8120cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0095000000-0c098e2b64d478a5e4d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-0190000000-d6d70ed69da9f27bee29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdl-3490000000-5a0e988988f81f967b03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3a6715be3231f63279bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ul0-0095000000-032bf9cb6539d3f7479aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1090000000-16932bcbf046cb12b8b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-a31baae7fa83b1a9cb20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l2r-0291000000-86360d0dc940679c31bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05be-1900000000-8071003485ecbea19dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-80caba83ca693b662223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-47ffb3556f0d805c33a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1390000000-6e12d642905fa15bfaf5Spectrum
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 IDHMDB0003955
FooDB IDFDB030282
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6990
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID221136
ChEBI ID27576
PubChem Compound ID252379
Kegg Compound IDC05290
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.