Stigmasterol

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-	[[Image:Stigmasterin.svg.png|thumb]]
-	'''Stigmasterol''' is a phytosterol with a molecular weight of 412.691 and a formula of C<sub>29</sub>H<sub>48</sub>O. It is also known as Wulzen anti-stiffness factor.
-	Stigmasterol is one of a group of plant sterols, or phytosterols, that includes beta-sitosterol, campesterol, ergosterol (provitamin D2), brassicasterol, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol.
-	The structures of beta-sitosterol and campesterol are virtually indistinguishable from that of cholesterol.	+	<table align='right' border=1>
		+	<tr><td>
		+	<jmol><jmolApplet>
		+	<size>200</size>
		+	<script>spin on;color atoms amino;</script>
		+	<uploadedFileContents>NPH406.SDF</uploadedFileContents>
		+	<color>black</color>
		+	</jmolApplet>
		+	</jmol>
		+	</td></tr></table>
		+	==Description==
-	==Properties==	+	==General Properties==
-	Phytosterols are insoluble in water but soluble in most organic solvents and contain one alcohol functional group.	+
-	Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus, or Mai men dong, and American Ginseng.	+	<b>*Molecular Weight</b>
-	==Availability==	+	412.69
-	Stigmasterol is also found in various vegetables, legumes, nuts, seeds and Raw unpasteurized milk. Pasteurization will inactivate stigmasterol.	+
-	It is used as a precursor in the manufacture of synthetic progesterone, a valuable human hormone that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids.	+	<b>*Molecular Formula</b>
-	==Drug Likeliness==	+	C<sub>2</sub><sub>9</sub>H<sub>4</sub><sub>8</sub>O
-	Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate, breast and colon cancers.	+
-	Studies have also indicated that a diet high in phytoesterols may inhibit the absorption of cholesterol and lower serum cholesterol levels by competing for intestinal absorption.	+	<b>*IUPAC NAME</b>
-	Studies with laboratory animals fed stigmasterol found that both cholesterol and sitosterol absorption decreased 23% and 30% respectively over a 6 week period.	+	(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
-	Phytosterols normally are broken down into bile.	+	<b>*Canonical Smiles</b>
		+
		+	CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C
		+
		+	<b>*Isomeric Smiles</b>
		+
		+	CC[C@H](C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C
		+
		+
		+	==PhysioChemical Properties==
		+
		+	<b>*Melting Point</b>
		+
		+	9.43(EST)
		+
		+	<b>*LogP</b>
		+
		+
		+
		+	<b>*Water Solubility</b>
		+
		+
		+
		+	==External Links==
		+	*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5280794]Pubchem
		+	*[http://www.genome.jp/dbget-bin/www_bget?compound+C05442]KEGG Compound
		+	*[http://www.hmdb.ca/metabolites/HMDB00937]Human Metabolome DataBase
		+
		+
		+	[[Categories:Hormones]]

---

Revision as of 00:00, 15 January 2001

Contents 1 Description 2 General Properties 3 PhysioChemical Properties 4 External Links

Description

General Properties

*Molecular Weight

412.69

*Molecular Formula

C₂₉H₄₈O

*IUPAC NAME

(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

*Canonical Smiles

CCC(C=CC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)C(C)C

*Isomeric Smiles

CC[C@H](C=C[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C

PhysioChemical Properties

*Melting Point

9.43(EST)

*LogP

*Water Solubility

External Links

• [1]Pubchem
• [2]KEGG Compound
• [3]Human Metabolome DataBase

Categories:Hormones