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Record Information
Version1.0
Creation Date2016-09-30 22:19:01 UTC
Update Date2020-05-21 16:29:04 UTC
BMDB IDBMDB0000053
Secondary Accession Numbers
  • BMDB00053
Metabolite Identification
Common NameAndrostenedione
DescriptionAndrostenedione, also known as fecundin, 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, androstenedione is considered to be a steroid lipid molecule. Androstenedione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Androstenedione exists in all living organisms, ranging from bacteria to humans. Androstenedione participates in a number of enzymatic reactions, within cattle. In particular, Androstenedione can be converted into androstanedione through its interaction with the enzyme 3-oxo-5-alpha-steroid 4-dehydrogenase 1. In addition, Androstenedione can be converted into 19-hydroxyandrost-4-ene-3,17-dione through the action of the enzyme cytochrome P450 19A1. In cattle, androstenedione is involved in the metabolic pathway called the androstenedione metabolism pathway. Androstenedione is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
4-Androstene-3,17-dioneChEBI
4-ANDROSTENE-3-17-dioneChEBI
delta(4)-Androsten-3,17-dioneChEBI
delta(4)-Androstene-3,17-dioneChEBI
Δ(4)-Androsten-3,17-dioneGenerator
Δ(4)-Androstene-3,17-dioneGenerator
(4)-Androsten-3,17-dioneHMDB
17-KetotestosteroneHMDB
3,17-Dioxoandrost-4-eneHMDB
4-Androsten-3,17-dioneHMDB
4-AndrostenedioneHMDB
Androst-4-ene-3,17-dioneHMDB, KEGG
AndrostendioneHMDB
D4-Androstene-3,17-dioneHMDB
delta4-AndrostenedioneHMDB
FecundinHMDB
delta 4 AndrostenedioneMeSH, HMDB
delta-4-AndrostenedioneMeSH, HMDB
4 Androstene 3,17 dioneMeSH, HMDB
AndrostenedioneHMDB
delta4-Androstene-3,17-dioneHMDB
Δ4-Androstene-3,17-dioneHMDB
Chemical FormulaC19H26O2
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS Registry Number63-05-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChI KeyAEMFNILZOJDQLW-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-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0578 mg/mLNot Available
LogP2.75HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-518e1ad38bcc73325b53View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-5172e05f9889ee2bfaf4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000f-8940000000-f2892fe3b281d44164c8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-007d-1960000000-167f1765b095da9d603bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-518e1ad38bcc73325b53View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-5910000000-5172e05f9889ee2bfaf4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0590000000-502d6b821317a01a1990View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-36e848ba16b141eef47bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-9600000000-712954fc35a84c8217deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-f8e9aa16b4b208b69f7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000f-8940000000-e12025ea2b7808c64b9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-6910000000-b616785c86a92f46158eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9800000000-73e545a1eb2232d55371View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-735473bc44dd70e29259View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-5790000000-114675a4457063901f2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-0347db9e9578e8d5d6f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05pc-0490000000-d4049441f1c172450dc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-4790000000-355bc0834a6465ecad30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-887b6f223b77c683ef99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-9dafdd780cca012f1fb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-2190000000-264074b1eefeed0e3103View in MoNA
MSMass Spectrum (Electron Ionization)splash10-059m-3940000000-9cb32ac21e46afb2829aView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Blood
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Milk
  • Ovary
  • Placenta
  • Prostate Tissue
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified<0.000545 uMNot SpecifiedNot Specified
Normal
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified0.00186 +/- 0.000354 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00103 +/- 0.000302 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00326 +/- 0.000946 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00147 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00101 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.00306 uMNot SpecifiedNot Specified
Normal
details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000545 uMNot SpecifiedNot Specified
Treated with estradiol benzoate and progesterone
details
BloodDetected and Quantified0.000716 uMNot SpecifiedNot Specified
Treated with estradiol benzoate
details
HMDB IDHMDB0000053
DrugBank IDDB01536
Phenol Explorer Compound IDNot Available
FooDB IDFDB030678
KNApSAcK IDC00003644
Chemspider ID5898
KEGG Compound IDC00280
BioCyc IDANDROST4ENE
BiGG ID2210012
Wikipedia LinkAndrostenedione
METLIN ID2795
PubChem Compound6128
PDB IDNot Available
ChEBI ID16422
References
Synthesis ReferenceEgorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Courant F, Antignac JP, Maume D, Monteau F, Andre F, Le Bizec B: Determination of naturally occurring oestrogens and androgens in retail samples of milk and eggs. Food Addit Contam. 2007 Dec;24(12):1358-66. doi: 10.1080/02652030701329637. [PubMed:17852390 ]
  2. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]

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
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis. Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol. Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione. Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA. Also 16-alpha hydroxylates androgens, relevant for estriol synthesis. 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:
CYP17A1
Uniprot ID:
P05185
Molecular weight:
57244.0
Reactions
17-Hydroxyprogesterone → Androstenedionedetails