Androsterone

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'''Androsterone''' Pubchem(5879) (ADT) is a [[steroid hormone]] with weak [[androgenic]] activity. It is made in the [[liver]] from the [[metabolism]] of [[testosterone]]. It was first isolated in 1931, by [[Adolf Friedrich Johann Butenandt]] and [[Kurt Tscherning]]. They distilled over 17000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to [[estrone]].
 +
[[Celery]] is claimed to contain androsterone however this is a mistake. Celery actually contains [[androstenone]], which has a different structure to Androsterone and is otherwise unrelated. Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a [[pheromone]]. Androsterone has been shown to naturally occur in [[pine]] [[pollen]] and is well known in many [[animal]] [[species]]. (2)
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Androsterone and its 3b [[isomer]] (epiandrosterone) are naturally produced by the enzyme 5aReductase from the adrenal hormone DHEA (dehydroepiandrosterone). Androsterone can also be converted from the natural steroids 5aAndrostanediol via 17b-Hydroxysteroid dehydrogenase or from 5aAndrostanedione via 3a-Hydroxysteroid dehydrogenase.  
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==Description==
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A metabolite of TESTOSTERONE or ANDROSTENEDIONE with a  3-alpha-hydroxyl group and without the double bond. The 3-beta  hydroxyl isomer is epiandrosterone.
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==General Properties==
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<b>*Molecular Weight</b>
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Androsterone provides the basic skeleton describing an androgen with a 3 a/b hydroxyl group and a 17 position ketone. Descriptive modifiers can be added like "epi" to signify a 3b hydroxyl and "#-ene" to signify the double bond placement. This basic structure can be modified in mammals by dehydrogenating it via many enzymes to create DHEA compounds that include 1-ene, 4-ene, 5-ene isomers. These isomers have been shown to be naturally occurring in mammals along with several unique structures including 4-Hydroxy-4-Dehydroepiandrosterone and 6-Keto-4-Dehydroepiandrosterone. Synthetically the combinations of dehydrogenated variants are vast and can include many unique structures.
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KEGG Pathway
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*Androgen and estrogen metabolism
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''List of PDB files having Androsterone as a Ligand:'''
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|-
 +
! style="background:brown; color:white" |MMDB ID
 +
! style="background:brown; color:white" |PDB ID
 +
! style="background:brown; color:white" |Reference
 +
|-
 +
|31178
 +
|1YB1
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|Lukacik P, Bunkoczi G, Kavanagh K, Ng S, Von Delft F, Bray J, Edwards A, Arrowsmith C, Sundstrom M, Oppermann U, Structural, Genomics Consortium (Sgc), 2004/12/18
 +
|-
 +
|31956
 +
|1X8J
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|Pakhomova S, Buck J, Newcomer METhe structures of the unique sulfotransferase retinol dehydratase with product and inhibitors provide insight into enzyme mechanism and inhibitionProtein Sci. v14, p.176-182
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|-
 +
|}
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{| border="1;width:100%; height:200px;style=text-align:center"
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|+'''Physiochemical properties of Androsterone:'''
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|-
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|-
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|Melting Point
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|185
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|deg C
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|  
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|EXP
 +
|-
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|log P (octanol-water)
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|3.69
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|(none)
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|  
 +
|EXP
 +
|-
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|Water Solubility
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|12
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|mg/L
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|23
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|EXP
 +
|-
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|Vapor Pressure
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|2.79E-08
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|mm Hg
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|25
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|EST
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|-
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|Henry's Law Constant
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|6.37E-09
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|atm-m3/mole
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|25
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|EST
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|-
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|Atmospheric OH Rate Constant
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|4.56E-11
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|cm3/molecule-sec
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|25
 +
|EST
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|-
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|}
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290.44
 
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<b>*Molecular Formula</b>
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==See also==
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* [[Androstadienone]]
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* [[Androstatrione]]
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* [[Androstenol]]
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* [[Androstenone]]
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* [[Dehydroepiandrosterone]]
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* [[Estratetraenol]]
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C<sub>1</sub><sub>9</sub>H<sub>3</sub><sub>0</sub>O<sub>2</sub>
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==External links==
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*[http://www.hmdb.ca/scripts/show_card.cgi?METABOCARD=HMDB00031 Androsterone entry in the HMDB]
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*
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<b>*IUPAC NAME</b>
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1. Experientia. 1979 Dec 15;35(12):1674-5.Links The boar-pheromone steroid identified in vegetables. Claus R, Hoppen HO.
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(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
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2. FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland
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<b>*Canonical Smiles</b>
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3. Rao MS, Ide H, Alvares K, Subbarao V, Reddy JK, Hechter O, Yeldandi AV. Comparative effects of dehydroepiandrosterone and related steroids on peroxisome proliferation in rat liver. Life Sci. 52(21):1709-16, 1993
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CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
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4.McGregor SJ, Erickson AJ. Identification of 5alpha-androst-1-ene-3beta,17beta-diol in the fat of Sus scrofa L.: a "nutritional supplement" not found previously in the food supply. J Nat Prod. 2003 Sep;66(9):1147-8.
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<b>*Isomeric Smiles</b>
 
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C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
 
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[[Category:Androgens]]
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==PhysioChemical Properties==
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[[Category:hormones]]
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[[Category:steroids]]
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<b>*Melting Point</b>
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[[Category:Pheromones]]
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185(EXP)
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<b>*LogP</b>
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3.69(EXP)
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<b>*Water Solubility</b>
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12(EXP) at 23C
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==External Links==
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5879]Pubchem
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*[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1YB1]]1YB1,[[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1X8J]]1X8J,
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C00523]]KEGG Compound
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*[http://www.hmdb.ca/metabolites/HMDB00031]Human Metabolome DataBase
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[[Categories:Hormones]]
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Revision as of 07:10, 13 February 2009

Androsterone Pubchem(5879) (ADT) is a steroid hormone with weak androgenic activity. It is made in the liver from the metabolism of testosterone. It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17000 litres of male urine, from which they got 50 milligrams of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Celery is claimed to contain androsterone however this is a mistake. Celery actually contains androstenone, which has a different structure to Androsterone and is otherwise unrelated. Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone. Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species. (2)

Androsterone and its 3b isomer (epiandrosterone) are naturally produced by the enzyme 5aReductase from the adrenal hormone DHEA (dehydroepiandrosterone). Androsterone can also be converted from the natural steroids 5aAndrostanediol via 17b-Hydroxysteroid dehydrogenase or from 5aAndrostanedione via 3a-Hydroxysteroid dehydrogenase.

Androsterone provides the basic skeleton describing an androgen with a 3 a/b hydroxyl group and a 17 position ketone. Descriptive modifiers can be added like "epi" to signify a 3b hydroxyl and "#-ene" to signify the double bond placement. This basic structure can be modified in mammals by dehydrogenating it via many enzymes to create DHEA compounds that include 1-ene, 4-ene, 5-ene isomers. These isomers have been shown to be naturally occurring in mammals along with several unique structures including 4-Hydroxy-4-Dehydroepiandrosterone and 6-Keto-4-Dehydroepiandrosterone. Synthetically the combinations of dehydrogenated variants are vast and can include many unique structures. KEGG Pathway

  • Androgen and estrogen metabolism
List of PDB files having Androsterone as a Ligand:
MMDB ID PDB ID Reference
31178 1YB1 Lukacik P, Bunkoczi G, Kavanagh K, Ng S, Von Delft F, Bray J, Edwards A, Arrowsmith C, Sundstrom M, Oppermann U, Structural, Genomics Consortium (Sgc), 2004/12/18
31956 1X8J Pakhomova S, Buck J, Newcomer METhe structures of the unique sulfotransferase retinol dehydratase with product and inhibitors provide insight into enzyme mechanism and inhibitionProtein Sci. v14, p.176-182
Physiochemical properties of Androsterone:
Physical Property Value Units Temp (deg C) Source
Melting Point 185 deg C EXP
log P (octanol-water) 3.69 (none) EXP
Water Solubility 12 mg/L 23 EXP
Vapor Pressure 2.79E-08 mm Hg 25 EST
Henry's Law Constant 6.37E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.56E-11 cm3/molecule-sec 25 EST


See also

External links

1. Experientia. 1979 Dec 15;35(12):1674-5.Links The boar-pheromone steroid identified in vegetables. Claus R, Hoppen HO.

2. FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland

3. Rao MS, Ide H, Alvares K, Subbarao V, Reddy JK, Hechter O, Yeldandi AV. Comparative effects of dehydroepiandrosterone and related steroids on peroxisome proliferation in rat liver. Life Sci. 52(21):1709-16, 1993

4.McGregor SJ, Erickson AJ. Identification of 5alpha-androst-1-ene-3beta,17beta-diol in the fat of Sus scrofa L.: a "nutritional supplement" not found previously in the food supply. J Nat Prod. 2003 Sep;66(9):1147-8.

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