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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-02-21 20:56:18 UTC
HMDB IDHMDB0000053
Secondary Accession Numbers
  • HMDB00053
Metabolite Identification
Common NameAndrostenedione
DescriptionAndrostenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.
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
AndrostendioneHMDB
D4-Androstene-3,17-dioneHMDB
Delta4-AndrostenedioneHMDB
FecundinHMDB
[4-14C]-AndrostenedioneHMDB
[4-14C]Androst-4-ene-3,17-dioneHMDB
delta 4 AndrostenedioneMeSH
delta-4-AndrostenedioneMeSH
4 Androstene 3,17 dioneMeSH
Chemical FormulaC19H26O2
Average Molecular Weight286.4085
Monoisotopic Molecular Weight286.193280076
IUPAC Name(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
Traditional Nameandrostenedione
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
DescriptionThis compound 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.058 mg/mLNot Available
LogP2.75HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
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
Polarizability33.2 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Fibroblasts
  • Gonads
  • Kidney
  • Liver
  • Muscle
  • Placenta
  • Prostate
  • Skin
  • Testes
Pathways
NameSMPDB/PathwhizKEGG
17-Beta Hydroxysteroid Dehydrogenase III DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Androgen and Estrogen MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleMap00150
Androstenedione MetabolismThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Aromatase deficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000698 uMNewborn (0-30 days old)Female
Normal
details
BloodDetected and Quantified0.00244-0.00768 uMNot SpecifiedNot SpecifiedNormal details
BloodDetected and Quantified<0.0140 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.00489 +/- 0.00196 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0059 (0.0023-0.0094) uMAdult (>18 years old)BothNormal
    • The Merck Manual,...
details
BloodDetected and Quantified0.00315 (0.00000-0.00630) uMAdult (>18 years old)FemaleNormal
    • The Merck Manual,...
details
BloodDetected but not Quantified Adult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.00524 +/- 0.00140 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000978-0.00803 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00061 +/- 0.00022 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified<0.00100 uMNot SpecifiedBothNormal details
BloodDetected and Quantified0.0022 (0.0010-0.0034) uMChildren (1-13 years old)BothNormal
    • Mayo Medical Labo...
details
BloodDetected and Quantified0.005 (0.0024-0.0070) uMAdolescent (13-18 years old)FemaleNormal
    • Mayo Medical Labo...
details
BloodDetected and Quantified0.0040 (0.0013-0.0066) uMChildren (1-13 years old)FemaleNormal
    • Mayo Medical Labo...
details
BloodDetected and Quantified0.001 (0.00034-0.00170) uMChildren (1-13 years old)FemaleNormal
    • Mayo Medical Labo...
details
BloodDetected and Quantified0.0057 (0.00069-0.01) uMAdult (>18 years old)FemaleNormal
    • Mayo Medical Labo...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00101 (0.00002-0.002) uMAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.090 +/- 0.058 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0068 +/- 0.0013 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000698-0.0583 uMNewborn (0-30 days old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.0066 +/- 0.0038 uMAdult (>18 years old)Female
Polycystic ovary syndrome (PCOS)
details
BloodDetected and Quantified0.00663 uMAdolescent (13-18 years old)Female
21-hydroxylase deficiency
details
BloodDetected and Quantified0-0.00244 uMAdult (>18 years old)Female
21-hydroxylase deficiency
details
BloodDetected and Quantified0.517 uMInfant (0-1 year old)Both
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)
details
BloodDetected and Quantified0.00154-0.0174 uMAdult (>18 years old)Female21-hydroxylase deficiency details
BloodDetected and Quantified0.00137 +/- 0.000800 uMNewborn (0-30 days old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.000810 +/- 0.00140 uMChildren (1-13 years old)Not Specified
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.000900-0.00420 uMAdult (>18 years old)MaleX-linked ichthyosis details
BloodDetected and Quantified0.0017 uMAdult (>18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0041 uMAdolescent (13-18 years old)Male
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.00175-0.0770 uMNewborn (0-30 days old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.000270-0.0480 uMChildren (1-13 years old)Both
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.000570 +/- 0.000200 uMChildren (1-13 years old)BothAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00103 +/- 0.00100 uMInfant (0-1 year old)Not SpecifiedAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00380 +/- 0.00100 uMAdult (>18 years old)MaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected and Quantified0.00430 +/- 0.00180 uMAdult (>18 years old)FemaleAdrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency details
BloodDetected but not Quantified Adult (>18 years old)Male
Schizophrenia
details
BloodDetected and Quantified<0.00003 uMAdult (>18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified<0.00003 uMAdolescent (13-18 years old)FemaleLipoid Adrenal Hyperplasia details
BloodDetected and Quantified0.00279-0.00454 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.12 uMNewborn (0-30 days old)Female
11-beta-hydroxylase deficiency
details
BloodDetected and Quantified0.00360-0.0227 uMChildren (1-13 years old)Both11-beta-hydroxylase deficiency details
BloodDetected and Quantified0.0090 +/- 0.0046 uMAdult (>18 years old)Female
Polycystic ovary syndrome (PCOS)
details
BloodDetected and Quantified0.0090 +/- 0.0065 uMAdult (>18 years old)BothCushing's syndrome details
BloodDetected and Quantified0.0031 +/- 0.0030 uMAdult (>18 years old)BothCushing's syndrome details
BloodDetected and Quantified0.000873 uMNewborn (0-30 days old)Female
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
details
UrineDetected but not Quantified Adult (>18 years old)Female
Ovarian cancer
details
UrineDetected and Quantified0.090 +/- 0.073 umol/mmol creatinineAdult (>18 years old)FemaleThyroid cancer details
UrineDetected and Quantified0.0017 +/- 0.00034 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.0025 +/- 0.00071 umol/mmol creatinineAdult (>18 years old)Both
Rheumatoid arthritis
details
UrineDetected and Quantified0.0025 +/- 0.00042 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
UrineDetected and Quantified0.0047 +/- 0.0005 umol/mmol creatinineAdult (>18 years old)Both
Systemic lupus erythematosus (SLE)
details
Associated Disorders and Diseases
Disease References
11-beta-Hydroxylase deficiency
  1. Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
21-Hydroxylase deficiency
  1. Warinner SA, Zimmerman D, Thompson GB, Grant CS: Study of three patients with congenital adrenal hyperplasia treated by bilateral adrenalectomy. World J Surg. 2000 Nov;24(11):1347-52. [PubMed:11038205 ]
  2. Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28. [PubMed:11826238 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
  2. Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ]
  3. Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
  1. Schwarz E, Liu A, Randall H, Haslip C, Keune F, Murray M, Longo N, Pasquali M: Use of steroid profiling by UPLC-MS/MS as a second tier test in newborn screening for congenital adrenal hyperplasia: the Utah experience. Pediatr Res. 2009 Aug;66(2):230-5. doi: 10.1203/PDR.0b013e3181aa3777. [PubMed:19390483 ]
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Cushing's Syndrome
  1. Mune T, Morita H, Yasuda K, Murayama M, Yamakita N, Miura K: Elevated plasma 19-hydroxyandrostenedione levels in Cushing's disease: stimulation with ACTH and inhibition with metyrapone. Clin Endocrinol (Oxf). 1993 Mar;38(3):265-72. [PubMed:8384536 ]
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Polycystic ovary syndrome
  1. Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. [PubMed:16890572 ]
Rheumatoid arthritis
  1. Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
  1. Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Lipoid Congenital Adrenal Hyperplasia
  1. Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
X-linked ichthyosis
  1. Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Associated OMIM IDs
  • 184700 (Polycystic ovary syndrome)
  • 181500 (Schizophrenia)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 202010 (11-beta-Hydroxylase deficiency)
  • 201910 (21-Hydroxylase deficiency)
  • 613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
  • 201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
  • 308100 (X-linked ichthyosis)
  • 201710 (Lipoid Congenital Adrenal Hyperplasia)
  • 180300 (Rheumatoid arthritis)
DrugBank IDDB01536
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021807
KNApSAcK IDC00003644
Chemspider ID5898
KEGG Compound IDC00280
BioCyc IDANDROST4ENE
BiGG ID2210012
Wikipedia LinkAndrostenedione
METLIN ID2795
PubChem Compound6128
PDB IDASD
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. Berkovitz GD, Guerami A, Brown TR, MacDonald PC, Migeon CJ: Familial gynecomastia with increased extraglandular aromatization of plasma carbon19-steroids. J Clin Invest. 1985 Jun;75(6):1763-9. [PubMed:3924954 ]
  2. Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. [PubMed:16855166 ]
  3. Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
  4. van Vloten WA, van Haselen CW, van Zuuren EJ, Gerlinger C, Heithecker R: The effect of 2 combined oral Contraceptives containing either drospirenone or cyproterone acetate on acne and seborrhea. Cutis. 2002 Apr;69(4 Suppl):2-15. [PubMed:12096825 ]
  5. Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2. [PubMed:15522925 ]
  6. Egloff M, Savoure N, Tardivel-Lacombe J, Massart C, Nicol M, Degrelle H: Influence of sex hormone binding globulin and serum albumin on the conversion of androstenedione to testosterone by human erythrocytes. Acta Endocrinol (Copenh). 1981 Jan;96(1):136-40. [PubMed:7192922 ]
  7. Zarrilli S, Lombardi G, Paesano L, Di Somma C, Colao A, Mirone V, De Rosa M: Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy. Andrologia. 2000 May;32(3):147-54. [PubMed:10863969 ]
  8. Heikkila R, Aho K, Heliovaara M, Hakama M, Marniemi J, Reunanen A, Knekt P: Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study. Cancer. 1999 Jul 15;86(2):312-5. [PubMed:10421267 ]
  9. Schlaghecke R, Kley HK, Kruskemper HL: The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul;44(1):23-33. [PubMed:6100340 ]
  10. King DS, Sharp RL, Vukovich MD, Brown GA, Reifenrath TA, Uhl NL, Parsons KA: Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. JAMA. 1999 Jun 2;281(21):2020-8. [PubMed:10359391 ]
  11. Johansson A, Henriksson A, Olofsson BO, Olsson T: Adrenal steroid dysregulation in dystrophia myotonica. J Intern Med. 1999 Apr;245(4):345-51. [PubMed:10356596 ]
  12. Atkinson G, Campbell DJ, Cawood ML, Oakey RE: Steroids in human intrauterine fluids of early pregnancy. Clin Endocrinol (Oxf). 1996 Apr;44(4):435-40. [PubMed:8706310 ]
  13. Zarrilli S, Paesano L, Mirone V, Finelli L, De Rosa M: [Evaluation of seminal and hormonal parameters in idiopathic varicocele before and after surgical intervention]. Chir Ital. 1998 Mar-Aug;50(2-4):21-8. [PubMed:11762080 ]
  14. Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. [PubMed:16890572 ]
  15. Thomson S, Wallace AM, Cook B: A 125I-radioimmunoassay for measuring androstenedione in serum and in blood-spot samples from neonates. Clin Chem. 1989 Aug;35(8):1706-12. [PubMed:2758640 ]
  16. Riikonen RS: How do cryptogenic and symptomatic infantile spasms differ? Review of biochemical studies in Finnish patients. J Child Neurol. 1996 Sep;11(5):383-8. [PubMed:8877606 ]
  17. Azurmendi A, Braza F, Sorozabal A, Garcia A, Braza P, Carreras MR, Munoz JM, Cardas J, Sanchez-Martin JR: Cognitive abilities, androgen levels, and body mass index in 5-year-old children. Horm Behav. 2005 Aug;48(2):187-95. [PubMed:15878571 ]
  18. Schairer C, Hill D, Sturgeon SR, Fears T, Mies C, Ziegler RG, Hoover RN, Sherman ME: Serum concentrations of estrogens, sex hormone binding globulin, and androgens and risk of breast hyperplasia in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2005 Jul;14(7):1660-5. [PubMed:16030098 ]
  19. Feldman PS, Kovacs K, Horvath E, Adelson GL: Malignant Leydig cell tumor: clinical, histologic and electron microscopic features. Cancer. 1982 Feb 15;49(4):714-21. [PubMed:7055782 ]
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  22. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
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  24. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 43 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
Reactions
Testosterone + NAD → Androstenedione + NADHdetails
Testosterone + NADP → Androstenedione + NADPHdetails
References
  1. Amin SA, Huang CC, Reierstad S, Lin Z, Arbieva Z, Wiley E, Saborian H, Haynes B, Cotterill H, Dowsett M, Bulun SE: Paracrine-stimulated gene expression profile favors estradiol production in breast tumors. Mol Cell Endocrinol. 2006 Jul 11;253(1-2):44-55. Epub 2006 Jun 2. [PubMed:16735089 ]
General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Reduced adrenal ferredoxin + Androstenedione + Oxygen → 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:
HSD17B2
Uniprot ID:
P37059
Molecular weight:
42784.75
Reactions
Testosterone + NAD → Androstenedione + NADHdetails
Testosterone + NAD → Androstenedione + NADH + Hydrogen Iondetails
References
  1. Su EJ, Cheng YH, Chatterton RT, Lin ZH, Yin P, Reierstad S, Innes J, Bulun SE: Regulation of 17-beta hydroxysteroid dehydrogenase type 2 in human placental endothelial cells. Biol Reprod. 2007 Sep;77(3):517-25. Epub 2007 May 30. [PubMed:17538076 ]
General function:
Involved in oxidoreductase activity
Specific function:
NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Molecular weight:
26973.56
Reactions
Testosterone + NAD → Androstenedione + NADHdetails
Testosterone + NAD → Androstenedione + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
Etiocholanedione + NADP → Hydrogen Ion + NADPH + Androstenedionedetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A2
Uniprot ID:
P31213
Molecular weight:
28407.035
Reactions
Androstanedione + Acceptor → Androstenedione + Reduced acceptordetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
Reactions
Androstanedione + Acceptor → Androstenedione + Reduced acceptordetails
General function:
Involved in oxidoreductase activity
Specific function:
Favors the reduction of androstenedione to testosterone. Uses NADPH while the two other EDH17B enzymes use NADH.
Gene Name:
HSD17B3
Uniprot ID:
P37058
Molecular weight:
34515.345
Reactions
Testosterone + NADP → Androstenedione + NADPHdetails
Testosterone + NADP → Androstenedione + NADPH + Hydrogen Iondetails
References
  1. Lindqvist A, Hughes IA, Andersson S: Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency. J Clin Endocrinol Metab. 2001 Feb;86(2):921-3. [PubMed:11158067 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365

Only showing the first 10 proteins. There are 43 proteins in total.