5-Cholesten-3β-ol-7-one - Moligand™,≥99% , CAS No.566-28-9

CAS: 566-28-9 Cat. No.: H130174 Molecular Weight: 400.64

GRADE & PURITY Moligand™, ≥99%

Synonyms

Q27133201 | A937398 | HY-113342 | (2,5-dimethyl-thiazol-4-yl)-acetic acid | 7-Keto Cholesterol (~98%) | CHEBI:64294 | 3beta-Hydroxycholest-5-en-7-one | HMS2236E05 | 2-Phenoxy-acetamidine HCl | 5-Cholesten-3-beta-ol-7-one | 5-Cholesten-3beta-ol-7-one | AS-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

5-Cholesten-3β-ol-7-one is an oxidation product of cholesterol, widely present in atherosclerotic plaques, and has a stronger atherogenic effect than cholesterol. 7-Ketocholesterol can inhibit the rate-limiting enzymes involved in bile acid and cholesterol synthesis, such as cholesterol 7α-hydroxylase and HMG-CoA reductase. 7-Ketocholesterol exhibits pro-inflammatory effects both in vivo and in vitro and can induce cell apoptosis (apoptosis).

Specifications

Synonyms

Q27133201 | A937398 | HY-113342 | (2, 5-dimethyl-thiazol-4-yl)-acetic acid | 7-Keto Cholesterol (~98%) | CHEBI:64294 | 3beta-Hydroxycholest-5-en-7-one | HMS2236E05 | 2-Phenoxy-acetamidine HCl | 5-Cholesten-3-beta-ol-7-one | 5-Cholesten-3beta-ol-7-one | AS-

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

It is a cholesterol derivative that decreases the membrane potential of lipid bilayers. It reportedly accumulates in atherosclerotic plaques that leads to apoptosis of vascular cells.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504756061
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756061
• Canonical Smiles: CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C
• IUPAC Name: (3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• InChIKey: YIKKMWSQVKJCOP-ABXCMAEBSA-N
• INCHI: 1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CC[C@@H](C4)O)C)C
• WGK Germany: 3
• Molecular Weight: 400.64
• Reaxy-Rn: 2063124
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2063124&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Cholestane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Cholestane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Cholesterols and derivatives
• Alternative Parents: 7-oxosteroids 3-beta-hydroxysteroids 3-beta-hydroxy delta-5-steroids Delta-5-steroids Cyclohexenones Secondary alcohols Cyclic alcohols and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Cholesterol - Cholesterol-skeleton - 3-hydroxy-delta-5-steroid - 3-hydroxysteroid - Hydroxysteroid - Oxosteroid - 3-beta-hydroxy-delta-5-steroid - 3-beta-hydroxysteroid - 7-oxosteroid - Delta-5-steroid - Cyclohexenone - Cyclic alcohol - Ketone - Secondary alcohol - Organooxygen compound - Alcohol - Carbonyl group - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
• External Descriptors: Cholesterol and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

RORA Tchem Nuclear receptor ROR-alpha (1 Activities)

Discover Target: RORA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

NPC1L1 Tclin Niemann-Pick C1-like protein 1 (346 Activities)

Discover Target: NPC1L1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

Discover Target: PLK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-29 (80576 Activities)

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U-937 (7138 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

Discover Target: POLI

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RORA Tchem Nuclear receptor ROR-alpha (562 Activities)

Discover Target: RORA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GMNN Tbio Geminin (128009 Activities)

Discover Target: GMNN

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

Discover Target: RAPGEF3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)

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PC-12 (7051 Activities)

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Vero (26788 Activities)

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C6 (2371 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility：DMSO ；Ethanol
• Sensitivity: Light sensitive
• Molecular Weight: 400.600 g/mol
• XLogP3: 7.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 400.334 Da
• Monoisotopic Mass: 400.334 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 663.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yueyuan Zhang, Sha Xu, Jianxin Xu, Fuchao Xu, Geng Lu, Jiawei Zhou, Shuangshuang Gu, Jun Wang.  (2023)  Prognostic value of plasma 7-ketocholesterol in sepsis.  CLINICA CHIMICA ACTA,      [PMID:37399884] [10.1016/j.cca.2023.117467]

2. Ge Bai, Chuan-Guo Ma, Yu-Yuan Hu, Shu-Jing Guo, Tong Wang.  (2023)  Chemical conversions of free phytosterols during the bleaching of corn oil.  FOOD CHEMISTRY,      [PMID:36731234] [10.1016/j.foodchem.2023.135512]

3. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang.  (2024)  The global phosphorylation landscape of mouse oocytes during meiotic maturation.  EMBO JOURNAL,      [PMID:39256562] [10.1038/s44318-024-00222-1]