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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]].
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| - | [[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.
| + | <table align='right' border=1> |
| | + | <tr><td> |
| | + | <jmol><jmolApplet> |
| | + | <size>200</size> |
| | + | <script>spin on;color atoms amino;</script> |
| | + | <uploadedFileContents>NPH118.SDF</uploadedFileContents> |
| | + | <color>black</color> |
| | + | </jmolApplet> |
| | + | </jmol> |
| | + | </td></tr></table> |
| | + | ==Description== |
| | + | A metabolite of TESTOSTERONE or ANDROSTENEDIONE with a 3-alpha-hydroxyl group and without the double bond. The 3-beta hydroxyl isomer is epiandrosterone. |
| | + | ==General Properties== |
| | | | |
| - | 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.
| + | <b>*Molecular Weight</b> |
| - | KEGG Pathway
| + | |
| - | *Androgen and estrogen metabolism | + | |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | |
| - | |+'''List of PDB files having Androsterone as a Ligand:'''
| + | |
| - | |-
| + | |
| - | ! style="background:brown; color:white" |MMDB ID
| + | |
| - | ! style="background:brown; color:white" |PDB ID
| + | |
| - | ! style="background:brown; color:white" |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
| + | |
| - | |-
| + | |
| - | |}
| + | |
| - | {| border="1;width:100%; height:200px;style=text-align:center"
| + | |
| - | |+'''Physiochemical properties of Androsterone:'''
| + | |
| - | |-
| + | |
| - | ! style="background:brown; color:white" |Physical Property
| + | |
| - | ! style="background:brown; color:white" |Value
| + | |
| - | ! style="background:brown; color:white" |Units
| + | |
| - | ! style="background:brown; color:white" |Temp (deg C)
| + | |
| - | ! style="background:brown; color:white" |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
| + | |
| - | |-
| + | |
| - | |}
| + | |
| | | | |
| | + | 290.44 |
| | | | |
| - | ==See also==
| + | <b>*Molecular Formula</b> |
| - | * [[Androstadienone]] | + | |
| - | * [[Androstatrione]]
| + | |
| - | * [[Androstenol]]
| + | |
| - | * [[Androstenone]]
| + | |
| - | * [[Dehydroepiandrosterone]]
| + | |
| - | * [[Estratetraenol]]
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| | | | |
| - | ==External links==
| + | C<sub>1</sub><sub>9</sub>H<sub>3</sub><sub>0</sub>O<sub>2</sub> |
| - | *[http://www.hmdb.ca/scripts/show_card.cgi?METABOCARD=HMDB00031 Androsterone entry in the HMDB]
| + | |
| - | *
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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.
| + | <b>*IUPAC NAME</b> |
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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
| + | (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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| - | 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
| + | <b>*Canonical Smiles</b> |
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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.
| + | CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O |
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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]] | + | |
| - | [[Category:hormones]] | + | ==PhysioChemical Properties== |
| - | [[Category:steroids]] | + | |
| - | [[Category:Pheromones]] | + | <b>*Melting Point</b> |
| | + | |
| | + | 185(EXP) |
| | + | |
| | + | <b>*LogP</b> |
| | + | |
| | + | 3.69(EXP) |
| | + | |
| | + | <b>*Water Solubility</b> |
| | + | |
| | + | 12(EXP) at 23C |
| | + | |
| | + | ==External Links== |
| | + | *[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5879]Pubchem |
| | + | *[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1YB1]]1YB1,[[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1X8J]]1X8J, |
| | + | *[http://www.genome.jp/dbget-bin/www_bget?compound+C00523]]KEGG Compound |
| | + | *[http://www.hmdb.ca/metabolites/HMDB00031]Human Metabolome DataBase |
| | + | |
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| | + | [[Categories:Hormones]] |
A metabolite of TESTOSTERONE or ANDROSTENEDIONE with a 3-alpha-hydroxyl group and without the double bond. The 3-beta hydroxyl isomer is epiandrosterone.
(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
