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
[Plants sterols and stanols: new prospects in prevention of ischemic heart disease (based on data published in the European Heart Journal, 1999, vol. 1 (Suppl S))].	2001	11234137
Oxidized plant sterols in human serum and lipid infusions as measured by combined gas-liquid chromatography-mass spectrometry.	2001 Dec	11734576
Apolipoprotein E phenotype regulates cholesterol absorption in healthy 13-month-old children--The STRIP Study.	2001 Dec	11726725
Cholesterol and all-cause mortality in Honolulu.	2001 Dec 1	11741659
Effects of plant sterols and stanols on lipid metabolism and cardiovascular risk.	2001 Feb	11383323
Genetic analysis of phytosterolaemia.	2001 Feb	11286381
Sterol composition of Aureoumbra lagunensis, the Texas brown tide alga.	2001 Jul	11397449
Plant sterols regulate rat vascular smooth muscle cell growth and prostacyclin release in culture.	2001 Jun	11427042
Fate of intravenously administered squalene and plant sterols in human subjects.	2001 Jun	11369807
Birth weight, subsequent growth, and cholesterol metabolism in children 8-12 years old born preterm.	2001 Mar	11207165
Anti-inflammatory and immunomodulating properties of a sterol fraction from Sideritis foetens Clem.	2001 May	11379762
Brassinosteroids. Plant counterparts to animal steroid hormones?	2002	12481548
Classification and class-modeling of "Riviera Ligure" extra-virgin olive oil using chemical-physical parameters.	2002 Apr 10	11929311
Inhibition of cholesterol biosynthesis by Delta22-unsaturated phytosterols via competitive inhibition of sterol Delta24-reductase in mammalian cells.	2002 Aug 15	12162789
Serum plant sterols as a potential risk factor for coronary heart disease.	2002 Dec	12489060
Effects of phytosterol ester-enriched margarine on plasma lipoproteins in mild to moderate hypercholesterolemia are related to basal cholesterol and fat intake.	2002 Feb	11833047
Acute effects of weight reduction on cholesterol metabolism in obese type 2 diabetes.	2002 Feb	11750274
Phytosterol content in American ginseng seed oil.	2002 Feb 13	11829639
Serum plant sterols and biliary cholesterol secretion in humans: studies with ursodeoxycholic acid.	2002 Jul	12091491
[3,3]-Claisen rearrangements in 24alpha-methyl steroid synthesis. Application to campesterol, crinosterol, and Delta25-crinosterol side chain construction.	2002 Jun	11996932
Consumption of tall oil-derived phytosterols in a chocolate matrix significantly decreases plasma total and low-density lipoprotein-cholesterol levels.	2002 Nov	12425728
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
Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation.	2002 Spring	12511107
Plant sterols lower LDL cholesterol without improving endothelial function in prepubertal children with familial hypercholesterolaemia.	2003	12971422
Plasma markers of cholesterol homeostasis and apolipoprotein B-100 kinetics in the metabolic syndrome.	2003 Apr	12690090
Antioxidant effects of phytosterol and its components.	2003 Aug	14598915
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
Oil goldenberry (Physalis peruviana L.).	2003 Feb 12	12568557
Efficiency of intestinal cholesterol absorption in humans is not related to apoE phenotype.	2003 Jan	12518038
Expression of a Streptomyces 3-hydroxysteroid oxidase gene in oilseeds for converting phytosterols to phytostanols.	2003 Jan	12475617
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
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
Ezetimibe: a first-in-class, novel cholesterol absorption inhibitor.	2003 Winter	14647533
Selective sterol accumulation in ABCG5/ABCG8-deficient mice.	2004 Feb	14657202

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