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Protostane

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Protostane
Names

IUPAC name Protostane^[1]
Systematic IUPAC name (1R,3aS,3bS,5aS,9aS,9bS,11aS)-3a,3b,6,6,9a-Pentamethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	70050-78-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:36483
ChemSpider	7827639
PubChem CID	9548716
UNII	7F8LXZ75AX^Y
CompTox Dashboard (EPA)	DTXSID601337032
InChI InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-29(7)24(23)13-14-26-28(6)18-10-17-27(4,5)25(28)16-20-30(26,29)8/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25+,26+,28+,29+,30+/m1/s1 Key: OORMXZNMRWBSTK-XJIBWFFZSA-N
SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@]2([C@H]1CC[C@@H]3[C@@]2(CC[C@@H]4[C@@]3(CCCC4(C)C)C)C)C
Properties
Chemical formula	C₃₀H₅₄
Molar mass	414.762 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Protostane is a tetracyclic triterpene, its natural distribution is primarily limited to the genus Alisma. It is so named because it is considered to be the "prototype" of steroids.^[2]

References

[edit]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1539. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

^ Zhao M, Gödecke T, Gunn J, Duan JA, Che CT (2013). "Protostane and Fusidane Triterpenes: A Mini-Review". Molecules. 18 (4): 4054–4080. doi:10.3390/molecules18044054. PMC 3901436. PMID 23563857.

v t e Tetracyclics
Classes	Polyketides Tetracenes Steroids
Antibiotics	Tetracyclines Tetracycline Chlortetracycline Demeclocycline Doxycycline Eravacycline Lymecycline Minocycline Omadacycline Oxytetracycline Rolitetracycline Sarecycline Glycylcycline Tigecycline Triterpenes Fusidanes Fusidic acid Helvolic acid Cephalosporin P₁
Antidepressants (TeCAs)	Azipramine Ciclopramine Esmirtazapine Mianserin Mirtazapine Naranol Oxaprotiline Setiptiline (teciptiline)
Steroids	Sex hormones Progestogens Acetomepregenol Chlormadinone acetate Danazol Delmadinone acetate Etonogestrel Gestodene Hydroxyprogesterone caproate Levonorgestrel Norethisterone Norgestrel Progesterone Segesterone acetate Tibolone Sterane Cholane Cholestane Ergostane Gonanes Androstane Estrane Pregnane Allopregnane Norpregnane Retropregnane Triterpenes Cycloartane Cucurbitacins Cucurbitane Dammarane Euphane Lanostane Protostane Sterols Phytosterols Campesterol beta-Sitosterol Cholesterol Stanol esters

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