23-epi-26-Deoxyactein , CAS No.501938-01-8

CAS: 501938-01-8 Cat. No.: E650487 Fórmula: C₃₇H₅₆O₁₀ Peso molecular: 660.83 PubChem CID: 21668683

Synonyms

23-epi-26-Deoxyactein (constituent of Black cohosh) | DTXSID0033388 | DTXCID60820004 | PD195634 | SCHEMBL563205 | Q27138581 | UNII-2A97XP2V7I | 23-EPI-26-DEOXYACTEIN [USP-RS] | [(1R,1'R,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-1,4',6',12',17',

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

23-epi-26-Deoxyactein is a natural and orally active anti-obesity and anti-cancer compound .

In Vitro

23-epi-26-Deoxyactein (DA :10 μM and 20 μM) inhibits 3T3-L1 adipogenesis through down-regulating the expression of C/ebpα , C/ebpβ , and Pparγ , which are the critical adipogenic transcription factors. 23-epi-26-Deoxyactein (DA) promotes mitochondrial biogenesis in pancreatic β-cells preventing methylglyoxal-induced oxidative cell damage and protects osteoblasts against Antimycin A-induced cell damage. 23-epi-26-Deoxyactein (DA) inhibits growth of the MCF7 human breast cancer cells and induces cell cycle arrest at G1 (IC 50 of 21μM). 23-epi-26-Deoxyactein (0.1-1 μM) protects osteoblasts against Antimycin A-induced cell damage . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Differentiation AssayCell Line: 3T3-L1 preadipocytes. Concentration: 0-50 μM. Incubation Time: 8 days. Result: 10 μM DA inhibited the adipogenesis of 3T3-L1 preadipocytes mainly at the early stage of differentiation.

In Vivo

23-epi-26-Deoxyactein (DA: 5 and 10 mg/kg/d) significantly lowers body weight gain, fat mass, and liver weight in HFD-fed mice. 23-epi-26-Deoxyactein (DA) also reduces insulin resistance and serum lipoprotein levels in HFD-fed mice . 23-epi-26-Deoxyactein (DA) promotes adipocyte lipolysis in mice through activating the AMPK signaling and SIRT1-FOXO1 pathway . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Diet induced obesity in C57BL/6 mice . Dosage: 1-10 mg/kg. Administration: Orally, daily for 12 weeks. Result: Lowered body weight gain, fat mass, and liver weight. 5 mg/kg/d DA significantly improved HFD-induced glucose intolerance.

Form:Solid

Especificaciones

Sinónimos

23-epi-26-Deoxyactein (constituent of Black cohosh) | DTXSID0033388 | DTXCID60820004 | PD195634 | SCHEMBL563205 | Q27138581 | UNII-2A97XP2V7I | 23-EPI-26-DEOXYACTEIN [USP-RS] | [(1R,1'R,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-1,4',6',12',17',

Mecanismos bioquímicos y fisiológicos

23-epi-26-Deoxyactein is a natural and orally active anti-obesity and anti-cancer compound.

Condiciones de almacenamiento de almacenamiento

Protected from light,Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Nombres e identificadores

Sonrisas canónicas

CC1CC2(C3C(O3)(CO2)C)OC4C1C5(C(CC67CC68CCC(C(C8CCC7C5(C4)C)(C)C)OC9C(C(C(CO9)O)O)O)OC(=O)C)C

IUPAC Name

[(1R,1'R,3'R,4R,4'R,5R,5'R,6'R,10'S,12'S,13'S,16'R,18'S,21'R)-1,4',6',12',17',17'-hexamethyl-18'-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyspiro[3,6-dioxabicyclo[3.1.0]hexane-4,8'-9-oxahexacyclo[11.9.0.01,21.04,12.05,10.016,21]docosane]-3'-yl] acetate

InChIKey

GCMGJWLOGKSUGX-WUHYQCRDSA-N

INCHI

1S/C37H56O10/c1-18-12-37(30-33(6,47-30)17-43-37)46-21-13-32(5)23-9-8-22-31(3,4)24(45-29-28(41)27(40)20(39)15-42-29)10-11-35(22)16-36(23,35)14-25(44-19(2)38)34(32,7)26(18)21/h18,20-30,39-41H,8-17H2,1-7H3/t18-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30-,32+,33-,34-,35-,36+,37-/m1/s1

Isómeros SMILES

C[C@@H]1C[C@]2([C@H]3[C@](O3)(CO2)C)O[C@@H]4[C@H]1[C@]5([C@@H](C[C@@]67C[C@@]68CC[C@@H](C([C@@H]8CC[C@H]7[C@@]5(C4)C)(C)C)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)OC(=O)C)C

CAS alternativo

501938-01-8

PubChem CID

21668683

Términos de entrada MeSH

23-epi-26-deoxy-actein;23-epi-26-deoxyactein

Peso molecular

660.83

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Cycloartanols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Steroids and steroid derivatives
• Subclass: Cycloartanols and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Cycloartanols and derivatives
• Alternative Parents: Triterpenoids Steroid esters O-glycosyl compounds Ketals 1,4-dioxanes Oxanes Monosaccharides Tetrahydrofurans Secondary alcohols Carboxylic acid esters Polyols Oxacyclic compounds Dialkyl ethers Monocarboxylic acids and derivatives Epoxides Hydrocarbon derivatives Organic oxides Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Cycloartanol-skeleton - 9b,19-cyclo-lanostane-skeleton - Cycloartane-skeleton - Triterpenoid - Steroid ester - Glycosyl compound - O-glycosyl compound - Ketal - Para-dioxane - Monosaccharide - Oxane - Tetrahydrofuran - Secondary alcohol - Carboxylic acid ester - Organoheterocyclic compound - Acetal - Monocarboxylic acid or derivatives - Oxacycle - Ether - Oxirane - Dialkyl ether - Polyol - Carboxylic acid derivative - Alcohol - Organic oxygen compound - Organic oxide - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.
• External Descriptors: triterpenoid

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

Propiedades químicas y físicas

• Peso molecular: 660.800 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 660.387 Da
• Monoisotopic Mass: 660.387 Da
• Topological Polar Surface Area: 136.000 Ų
• Heavy Atom Count: 47
• Formal Charge: 0
• Complexity: 1360.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 18
• 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

Preguntas frecuentes

How should this product be stored?

Store at ?80 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 501938-01-8, the molecular formula is C37H56O10, and the molecular weight is 660.83 g/mol. InChIKey GCMGJWLOGKSUGX-WUHYQCRDSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.