CAMPESTEROL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H48O
Molecular Weight	400.6812
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@]([H])(C)CC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O

InChI

InChIKey=SGNBVLSWZMBQTH-PODYLUTMSA-N

InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20-,22+,23+,24-,25+,26+,27+,28-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H48O
Molecular Weight	400.6812
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosinase 41 Target ID: CHEMBL3318 Sources: Lim, T.K. (2016) Edible Medicinal and Non-Medicinal Plants, page 206, retrieved from: https://books.google.ru/books?id=d42RCwAAQBAJ	Inhibitor 7728
Target ID: Cholesterol absorption Sources: https://www.ncbi.nlm.nih.gov/pubmed/9560801	Inhibitor 7728

PubMed

Title	Date	PubMed
Phytosterols reduce in vitro metastatic ability of MDA-MB-231 human breast cancer cells.	2001	11962251
Relationship of genetic variation in genes encoding apolipoprotein A-IV, scavenger receptor BI, HMG-CoA reductase, CETP and apolipoprotein E with cholesterol metabolism and the response to plant stanol ester consumption.	2002 Apr	11952809
Evidence for multiple sterol methyl transferase pathways in Pneumocystis carinii.	2002 Dec	12617472
Comparison of the hepatic clearances of campesterol, sitosterol, and cholesterol in healthy subjects suggests that efflux transporters controlling intestinal sterol absorption also regulate biliary secretion.	2002 Dec	12427790
Overexpression in Catharanthus roseus hairy roots of a truncated hamster 3-hydroxy-3-methylglutaryl-CoA reductase gene.	2002 Feb	11996224
Interactions between sterol biosynthesis genes in embryonic development of Arabidopsis.	2002 Jul	12100483
Profile of cholesterol-related sterols in aged amyloid precursor protein transgenic mouse brain.	2002 Jul	12091492
Serum plant sterols and biliary cholesterol secretion in humans: studies with ursodeoxycholic acid.	2002 Jul	12091491
Micellar distribution of cholesterol and phytosterols after duodenal plant stanol ester infusion.	2002 Jun	12016126
[3,3]-Claisen rearrangements in 24alpha-methyl steroid synthesis. Application to campesterol, crinosterol, and Delta25-crinosterol side chain construction.	2002 Jun	11996932
Effects of calcium and plant sterols on serum lipids in obese Zucker rats on a low-fat diet.	2002 Mar	12064332
Effects of 5-campestenone (24-methylcholest-5-en-3-one) on the type 2 diabetes mellitus model animal C57BL/KsJ-db/db mice.	2002 Mar	11972300
Consumption of tall oil-derived phytosterols in a chocolate matrix significantly decreases plasma total and low-density lipoprotein-cholesterol levels.	2002 Nov	12425728
Specificity of the commonly used enzymatic assay for plasma cholesterol determination.	2002 Nov	12401826
Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of gibberellins in Arabidopsis.	2002 Nov 22	12228237
Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed.	2002 Sep	12226510
Ineffective decrease of serum cholesterol by simvastatin in a subgroup of hypercholesterolemic coronary patients.	2002 Sep	12119203
Phytonutrient deficiency: the place of palm fruit.	2003	14506002
Plant sterols lower LDL cholesterol without improving endothelial function in prepubertal children with familial hypercholesterolaemia.	2003	12971422
[Lipid metabolism in anorexia nervosa].	2003	12920792
Plasma markers of cholesterol homeostasis and apolipoprotein B-100 kinetics in the metabolic syndrome.	2003 Apr	12690090
Relationships between cholesterol homoeostasis and triacylglycerol-rich lipoprotein remnant metabolism in the metabolic syndrome.	2003 Apr	12653682
Presence of phytosterol oxides in crude vegetable oils and their fate during refining.	2003 Apr 9	12670187
Genetic analysis of indicators of cholesterol synthesis and absorption: lathosterol and phytosterols in Dutch twins and their parents.	2003 Aug	14511438
[Hyperlipidemia: therapeutic principles in clinical practice].	2003 Dec 15	14685674
Determination of sterol and fatty acid compositions, oxidative stability, and nutritional value of six walnut (Juglans regia L.) cultivars grown in Portugal.	2003 Dec 17	14664531
Effect of phytosterols on cholesterol metabolism and MAP kinase in MDA-MB-231 human breast cancer cells.	2003 Feb	12667603
Serum noncholesterol sterols during inhibition of cholesterol synthesis by statins.	2003 Feb	12577049
Expression of a Streptomyces 3-hydroxysteroid oxidase gene in oilseeds for converting phytosterols to phytostanols.	2003 Jan	12475617
Solid-phase extraction-thin-layer chromatography-gas chromatography method for the detection of hazelnut oil in olive oils by determination of esterified sterols.	2003 Jan 24	12580489
Serum cholesterol, precursors and metabolites and cognitive performance in an aging population.	2003 Jan-Feb	12493560
Physical stability of a microcrystalline beta-sitosterol suspension in oil.	2003 Jul	12885381
Effects of various amounts of dietary plant sterol esters on plasma and hepatic sterol concentration and aortic foam cell formation of cholesterol-fed hamsters.	2003 Jul	12860249
Effect of a statin on hepatic apolipoprotein B-100 secretion and plasma campesterol levels in the metabolic syndrome.	2003 Jul	12821974
Sitosterolaemia and xanthomatosis in a child.	2003 Jun	12777658
Response of obligate heterozygotes for phytosterolemia to a low-fat diet and to a plant sterol ester dietary challenge.	2003 Jun	12671028
The rat STSL locus: characterization, chromosomal assignment, and genetic variations in sitosterolemic hypertensive rats.	2003 Jun 3	12783625
Non-nutritive bioactive constituents of plants: phytosterols.	2003 Mar	12747220
Comparison of the contents of the main biochemical compounds and the antioxidant activity of some Spanish olive oils as determined by four different radical scavenging tests.	2003 Mar	12742543
Comparison of the intestinal uptake of cholesterol, plant sterols, and stanols in mice.	2003 Mar	12562824
Cholesterol metabolism in 8 to 12-year-old children born preterm or at term.	2003 May	12839278
Safety of long-term consumption of plant sterol esters-enriched spread.	2003 May	12771969
Red cell and plasma plant sterols are related during consumption of plant stanol and sterol ester spreads in children with hypercholesterolemia.	2003 May	12756385
The role of sterols in plant growth and development.	2003 May	12689617
Effects of ileum transplantation and chronic rejection on absorption and synthesis of cholesterol in pigs.	2003 Nov	14574608
Application of comprehensive two-dimensional gas chromatography to the quantification of overlapping faecal sterols.	2003 Nov 26	14650615
ABCG5 and ABCG8 are obligate heterodimers for protein trafficking and biliary cholesterol excretion.	2003 Nov 28	14504269
Analysis of plant sterol and stanol esters in cholesterol-lowering spreads and beverages using high-performance liquid chromatography-atmospheric pressure chemical ionization-mass spectroscopy.	2003 Sep 10	12952413
Ezetimibe: a first-in-class, novel cholesterol absorption inhibitor.	2003 Winter	14647533
Down-regulation of hepatic and intestinal Abcg5 and Abcg8 expression associated with altered sterol fluxes in rats with streptozotocin-induced diabetes.	2004 Jan	14618236

Patents

Substance Class	Chemical Created by `admin` on `Sat Jun 26 03:28:53 UTC 2021` Edited by `admin` on `Sat Jun 26 03:28:53 UTC 2021`
Record UNII	5L5O665639
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAMPESTEROL

Common Name

English

24.ALPHA.-METHYLCHOLESTEROL

Common Name

English

(3.BETA.,24R)-ERGOST-5-EN-3-OL

Systematic Name

English

CAMPESTEROL [WHO-DD]

Common Name

English

NSC-224330

Code

English

.DELTA.5-24-ISOERGOSTEN-3.BETA.-OL

Common Name

English

CAMPESTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]

Common Name

English

24(R)-METHYLCHOLESTEROL

Systematic Name

English

CAMPESTEROL [MI]

Common Name

English

CAMPESTEROL (CONSTITUENT OF PYGEUM) [DSC]

Common Name

English

Classification Tree Code System Code

LOINC

58464-9