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Revision as of 13:16, 26 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'KEGG', 'CASNo').← Previous edit		Latest revision as of 05:52, 13 October 2024 edit undoCrafterNova (talk | contribs)Extended confirmed users16,642 edits +linksTag: 2017 wikitext editor
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			{{Short description|Tetracyclic hydrocarbon parent of the steroids}}
			{{For|the closely related derivatives of gonane|Sterane}}
	{{Chembox		{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 424869490		| verifiedrevid = 457481383
	| ImageFile = gonane.png		| ImageFile = Gonane.png
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageName Stereo, skeletal formula of gonane ((1R,2S,10S,11R,15S)-heptadecane) with all chiral centres hydrogenised		| ImageName = Stereo, skeletal formula of gonane ((1R,2S,10S,11R,15S)-heptadecane) with all chiral centres hydrogenised
			| ImageFile1 = Steran num ABCD.svg
	| PIN = 2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-Hexadecahydro-1''H''-cyclopentaphenanthrene{{Citation needed|date = October 2011}}
			| ImageSize1 =
	| OtherNames = 18-Norestrane{{Citation needed|date = October 2011}}
			| ImageAlt1 =
⚫	| Section1 = {{Chembox Identifiers
			| ImageName1 = Carbon numbering in gonane
	| CASNo = <!-- blanked - oldvalue: 4732-76-7 -->
			| IUPACName = 5ξ-Gonane
⚫	| CASNo_Ref = {{cascite|changed|??}}
	| CASNo_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>		| SystematicName = (3a''R'',3b''S'',5a''Ξ'',9a''S'',9b''R'',11a''S'')-Hexadecahydro-1''H''-cyclopentaphenanthrene
	| PubChem = 1108		| OtherNames =
		⚫	|Section1={{Chembox Identifiers
	| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
	| PubChem1 = 6857523		| CASNo = 4732-76-7
	| PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}		| CASNo_Ref = {{cascite|changed|??}}
	| PubChem1_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>		| CASNo_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>
	| PubChem2 = 6857525		| PubChem = 1108
			| PubChem1 = 6857523
	| PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}
	| PubChem2_Comment = <small>(1''R'',2''S'',7''R'',10''S'',11''R'',15''S'')- heptadecane</small>		| PubChem1_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>
	| PubChem3 = 6857524		| PubChem2 = 6857525
		⚫	| PubChem2_Comment = <small>(1''R'',2''S'',7''R'',10''S'',11''R'',15''S'')- heptadecane</small>
	| PubChem3_Ref = {{Pubchemcite|correct|Pubchem}}
			| PubChem3 = 6857524
⚫	| PubChem3_Comment = <small>(1''R'',2''S'',7''S'',10''S'',11''R'',15''S'')- heptadecane</small>
		⚫	| PubChem3_Comment = <small>(1''R'',2''S'',7''S'',10''S'',11''R'',15''S'')- heptadecane</small>
⚫	| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			<!-- chaotic and inconsistent ID numbering; made assumptions. 25 Nov 2014. -->
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 5256859		| ChemSpiderID = 5256859
	| ChemSpiderID3 = 1077		| ChemSpiderID3 = 1077
	| ChemSpiderID3_Ref = {{chemspidercite|changed|chemspider}}		| ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>
	| ChemSpiderID1 = 5256859		| ChemSpiderID1 = 5256861
	| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID1_Comment = <small>(1''R'',2''S'',10''S'',11''R'',15''S'')- heptadecane</small>
		⚫	| ChemSpiderID1_Comment = <small>(1''R'',2''S'',7''R'',10''S'',11''R'',15''S'')- heptadecane</small>
	| ChemSpiderID1 = 5256861
		⚫	| ChemSpiderID2 = 5256860
	| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
⚫	| ChemSpiderID1_Comment = <small>(1''R'',2''S'',7''R'',10''S'',11''R'',15''S'')- heptadecane</small>
			| ChemSpiderID2_Comment = <small>(1''R'',2''S'',7''S'',10''S'',11''R'',15''S'')- heptadecane</small>
⚫	| ChemSpiderID2 = 5256860
			| KEGG = C19639
⚫	| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| KEGG_Ref = {{keggcite|changed|kegg}}
⚫	| ChemSpiderID2_Comment = <small>(1''R'',2''S'',7''S'',10''S'',11''R'',15''S'')- heptadecane</small>
		⚫	| ChEBI = 35528
	| KEGG = <!-- blanked - oldvalue: C19639 -->
	| KEGG_Ref = {{keggcite|changed|kegg}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| SMILES = C2C1(CCCC1)3CC4(3C2)CCC4
⚫	| ChEBI = 35528
		⚫	| StdInChI = 1S/C17H28/c1-2-6-14-12(4-1)8-10-17-15-7-3-5-13(15)9-11-16(14)17/h12-17H,1-11H2/t12?,13-,14-,15+,16+,17-/m0/s1
	| ChEBI_Ref = {{ebicite|changed|EBI}}
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| SMILES = C2C1(CCCC1)3CC4(3C2)CCC4
		⚫	| StdInChIKey = UACIBCPNAKBWHX-CTBOZYAPSA-N
⚫	| StdInChI = 1S/C17H28/c1-2-6-14-12(4-1)8-10-17-15-7-3-5-13(15)9-11-16(14)17/h12-17H,1-11H2/t12?,13-,14-,15+,16+,17-/m0/s1
	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	}}
⚫	| StdInChIKey = UACIBCPNAKBWHX-CTBOZYAPSA-N
		⚫	|Section2={{Chembox Properties
	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
		⚫	| C=17 | H=28
⚫	}}
		⚫	}}
⚫	| Section2 = {{Chembox Properties
	| C = 17
⚫	| H = 28
	| ExactMass = 232.219100896 g mol<sup>-1</sup>
⚫	}}
	}}		}}
			'''Gonane''' ('''cyclopentanoperhydrophenanthrene''') is a chemical compound with formula {{chem|C|17|H|28}}, whose structure consists of four ] rings ] together: three ] units and one ]. It can also be viewed as the result of fusing a cyclopentane molecule with a fully ] molecule of ], hence the more descriptive name "'''perhydrocyclopentaphenanthrene'''". The non-systematic version of the above name is "cyclopentanoperhydrophenanthrene".<ref name="Yang et al. 2023" />
	'''Gonane''' is a steroid nucleus. Gonane can exist as sixty-four ]s, the most common are known as 5α-gonane and 5β-gonane.
			It has no double bonds, that is, it is completely ] and is considered the main structure of ]s, often referred to as the '''steroid nucleus'''.<ref name="Yang et al. 2023">{{Cite journal |last1=Yang |first1=Yanqing |last2=Krin |first2=Anna |last3=Cai |first3=Xiaoli |last4=Poopari |first4=Mohammad Reza |last5=Zhang |first5=Yuefei |last6=Cheeseman |first6=James R. |last7=Xu |first7=Yunjie |date=2023-01-12 |title=Conformations of Steroid Hormones: Infrared and Vibrational Circular Dichroism Spectroscopy |journal=Molecules (Basel, Switzerland) |volume=28 |issue=2 |pages=771 |doi=10.3390/molecules28020771 |issn=1420-3049 |pmc=9864676 |pmid=36677830 |doi-access=free }}</ref> There are many forms of gonane, but only a few occur naturally in living organisms. Some common forms include 5α-gonane and 5β-gonane. ], ], and ] are derivatives of gonane with additional methyl or ethyl groups attached to certain carbon positions. The term gonane is also used to describe a group of ]s that are similar to ] but have a slightly different structure than other hormones like estranes.
			==Significance==
			Gonane is a significant chemical compound in the family of ]s because its structure comprises four hydrocarbon rings fused together, consisting of three cyclohexane units and one cyclopentane, which is often referred to as the "steroid nucleus" and serves as the parent compound for steroids.
			The discovery of gonane and its role as a steroid nucleus has been fundamental in understanding the structure and function of various ] hormones. The numbering of steroid rings is determined based on the skeletal structure of gonane, providing a framework for the classification and identification of different steroids.
			==Usage of the term==
			The term gonane is also used to refer to a group of ]s<ref name="Loiseau et al. 2018">{{Cite journal |last1=Loiseau |first1=Camille |last2=Cayetanot |first2=Florence |last3=Joubert |first3=Fanny |last4=Perrin-Terrin |first4=Anne S. |last5=Cardot |first5=Philippe |last6=Fiamma |first6=Marie N. |last7=Frugiere |first7=Alain |last8=Straus |first8=Christian |last9=Bodineau |first9=Laurence |date=2018-11-02 |title=Current Perspectives for the use of Gonane Progesteronergic Drugs in the Treatment of Central Hypoventilation Syndromes |doi-access=free |journal=Current Neuropharmacology |volume=16 |issue=10 |pages=1433–1454 |doi=10.2174/1570159X15666170719104605 |pmc=6295933 |pmid=28721821}}</ref> that are carbon 18-homologated 19-nortestosterone derivatives including ] and its ]s.<ref name="Edgren-Stanczyk1999">{{Cite journal |last1=Edgren |first1=Richard A. |last2=Stanczyk |first2=Frank Z. |date=December 1999 |title=Nomenclature of the gonane progestins |url=https://linkinghub.elsevier.com/retrieve/pii/S0010782499001018 |journal=Contraception |volume=60 |issue=6 |pages=313 |doi=10.1016/S0010-7824(99)00101-8|pmid=10715364 }}</ref> This term is used in this way in order to distinguish them from ]s, which are also 19-nortestosterone derivatives.<ref name="Edgren-Stanczyk1999" />
			== Structure ==
			Gonane is a ] ] with no double bonds. It is formally the parent compound of the ]s, hence it is called the "steroid nucleus".<ref name="Yang et al. 2023" /><ref name="FugmannLang-Fugmann2014">{{cite book|author1=Burkhard Fugmann|author2=Susanne Lang-Fugmann|author3=Wolfgang Steglich|title=RÖMPP Encyclopedia Natural Products, 1st Edition, 2000|url=https://books.google.com/books?id=PNyeAwAAQBAJ&pg=PT1918|date=28 May 2014|oclc=1389366313|publisher=Thieme|isbn=9783131795519|pages=1918–}}</ref><ref name="Speight2010">{{cite book|last=Speight|first=James G.|title=Handbook of Industrial Hydrocarbon Processes|url=https://books.google.com/books?id=EykJ2OyEHfsC&pg=PA474|oclc=750151056|date=24 December 2010|publisher=Gulf Professional Publishing|isbn=9780080942711|pages=474–}}</ref> Some important gonane derivatives are the ]s, characterized by ]s at the C10 and C13 positions and a ] at the C17 position.<ref name="Speight2010" />
			Because gonane has six ], it has 64 (2<sup>6</sup>) theoretically possible ]s,<ref name="FugmannLang-Fugmann2014" /> that differ on the position of the lone hydrogens at carbons 5, 8, 9, 10, 13 and 14 in the direction perpendicular to the mean plane of the carbons. However, only a few of these stereoisomers occur in living organisms.<ref name="FugmannLang-Fugmann2014" /> The most common are ] and ].
	<gallery>		<gallery>
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	</gallery>		</gallery>
			<gallery>
			File:AB-trans-Gonan.svg|5α-Gonane, side-perspective view
			File:AB-cis-Gonan.svg|5β-Gonane, side-perspective view
			</gallery>
			==Variants==
			] (C18) is the 13β-methyl variant of gonane, ] (C19) is the 10β,13β-dimethyl variant of gonane, and ] (C21) is the 10β,13β-dimethyl, 17β-] variant of gonane.<ref name="Sriram2010">{{cite book|author=D. Sriram|title=Medicinal Chemistry|url=https://books.google.com/books?id=tUSLclf_NoQC&pg=PA594|date=1 September 2010|publisher=Pearson Education India|isbn=978-81-317-3144-4|pages=594–}}</ref><ref name="BaulieuKelly1990">{{cite book|author1=Etienne-Emile Baulieu|author2=Paul A. Kelly|title=Hormones: From Molecules to Disease|url=https://books.google.com/books?id=Seddp4-dulIC&pg=PA391|date=30 November 1990|publisher=Springer Science & Business Media|isbn=978-0-412-02791-8|pages=391–}}</ref>
			==References==
			{{Reflist}}
			{{Tetracyclics}}
	{{Steroid classification}}		{{Steroid classification}}
	]		]
			]
			]
	{{Hydrocarbon-stub}}		{{Hydrocarbon-stub}}
	{{Steroid-stub}}		{{Steroid-stub}}
	]
	]
	]
	]