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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
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
| Canonical Smiles | 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 |
| Isomeric 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 |
| Alternate CAS | 501938-01-8 |
| PubChem CID | 21668683 |
| MeSH Entry Terms | 23-epi-26-deoxy-actein;23-epi-26-deoxyactein |
| Molecular Weight | 660.83 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | 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 |
| Description | This compound belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. |
| External Descriptors | triterpenoid |
| Molecular Weight | 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 |
