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Record Information
Version1.0
Creation Date2016-09-30 23:07:03 UTC
Update Date2020-05-21 16:29:04 UTC
BMDB IDBMDB0003955
Secondary Accession Numbers
  • BMDB03955
Metabolite Identification
Common Name19-Hydroxyandrost-4-ene-3,17-dione
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.
Structure
Thumb
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 Weight302.4079
Monoisotopic Molecular Weight302.188194698
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
CAS Registry Number510-64-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CO
InChI Identifier
InChI=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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufu-4910000000-ca91f3850d2822c36110View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0ufu-4910000000-acb494bbf38c6f0ab6aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0zi3-3920000000-2fb97be8369cef8834c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0ug0-3920000000-088095d0d94653a7ded1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufu-4910000000-ca91f3850d2822c36110View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ufu-4910000000-acb494bbf38c6f0ab6aeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0zi3-3920000000-2fb97be8369cef8834c8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ug0-3920000000-088095d0d94653a7ded1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052o-2920000000-719a80545e9031debcbaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000f-3920000000-25496932221b91188e02View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0290000000-4f45d95c38d59fa1da5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r2-1239000000-c5d6f655f6699da8120cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0095000000-0c098e2b64d478a5e4d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-0190000000-d6d70ed69da9f27bee29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdl-3490000000-5a0e988988f81f967b03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3a6715be3231f63279bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ul0-0095000000-032bf9cb6539d3f7479aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1090000000-16932bcbf046cb12b8b5View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003955
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030282
KNApSAcK IDNot Available
Chemspider ID221136
KEGG Compound IDC05290
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6990
PubChem Compound252379
PDB IDNot Available
ChEBI ID27576
References
Synthesis ReferenceUeberwasser, 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.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively. Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid. Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen. Also displays 2-hydroxylase activity toward estrone. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:
CYP19A1
Uniprot ID:
P46194
Molecular weight:
58090.0
Reactions
Androstenedione + Oxygen + Reduced flavoprotein → 19-Hydroxyandrost-4-ene-3,17-dione + Water + Oxidized flavoproteindetails