Euphorbiasteroid - ≥99% , CAS No.28649-59-4

CAS: 28649-59-4 Cat. No.: E413070 Molecular Weight: 552.66

GRADE & PURITY ≥99%

Synonyms

Euphorbia factor L1 | Benzeneacetic acid,(1aR,​2'R,​2E,​4aR,​6S,​7S,​7aR,​8S,​11aS)​-​4a,​8-​bis(acetyloxy)​-​1,​1a,​4,​4a,​5,​6,​7,​7a,​8,​10,​11,​11a-​dodecahydro-​1,​1,​3,​6-​tetramethyl-​4-​oxospiro[9H-​cyclopenta[a]​cyclopropa[f]​cycloundecene-​9,​2'

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Euphorbiasteroid Euphorbiasteroid (Euphorbia factor L1), a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells through activation of the AMPK pathway and induces HL-60 cells to apoptosis via promoting Bcl-2/Bax apoptotic signaling pathway in a dose-dependent manner. Euphorbiasteroid is a tricyclic diperpene of Euphorbia lathyris L., inhibits tyrosinase, and increases the phosphorylation of AMPK, with anti-cancer, anti-virus, anti-obesity and multidrug resistance-modulating effect.

In vitro

Euphorbiasteroid suppresses adipogenic differentiation of 3T3‐L1 cells, mainly at the early stage, and stimulates the AMPK signalling pathway. The anti-adipogenic effects of euphorbiasteroid could possibly be attributed to activation of the AMPK pathway, by decreasing the level of FAS and its up-regulators, including C/EBPs, PPAR-γ and SREBP-1c, without involving insulin signalling pathway. Euphorbiasteroid could be a transport substrate for P-gp that can effectively inhibit P-gp-mediated drug transport and reverse resistance to anticancer drugs in MES-SA/Dx5 cells.

Cell Research(from reference)

Concentrations：0-50 μM 

Incubation Time：2\u2009days 

Specifications

Synonyms

Euphorbia factor L1 | Benzeneacetic acid, (1aR, ​2'R, ​2E, ​4aR, ​6S, ​7S, ​7aR, ​8S, ​11aS)​-​4a, ​8-​bis(acetyloxy)​-​1, ​1a, ​4, ​4a, ​5, ​6, ​7, ​7a, ​8, ​10, ​11, ​11a-​dodecahydro-​1, ​1, ​3, ​6-​tetramethyl-​4-​oxospiro[9H-​cyclopenta[a]​cyclopropa[f]​cycloundecene-​9, ​2'

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Euphorbiasteroid (Euphorbia factor L1), a component of Euphorbia lathyris L., inhibits adipogenesis of 3T3-L1 cells through activation of the AMPK pathway and induces HL-60 cells to apoptosis via promoting Bcl-2/Bax apoptotic signaling pathway in a dose-d

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥99%

Product Properties

• ALogP: 4.183
• hba_count: 8
• Rotatable Bond: 8

Names and Identifiers

• Pubchem Sid: 504767980
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504767980
• Canonical Smiles: CC1CC2(C(C1OC(=O)CC3=CC=CC=C3)C(C4(CCC5C(C5(C)C)C=C(C2=O)C)CO4)OC(=O)C)OC(=O)C
• IUPAC Name: [(1'R,2R,3'E,5'R,7'S,11'S,12'R,13'S,14'S)-1',11'-diacetyloxy-3',6',6',14'-tetramethyl-2'-oxospiro[oxirane-2,10'-tricyclo[10.3.0.05,7]pentadec-3-ene]-13'-yl] 2-phenylacetate
• InChIKey: SDGDWRYYHQOQOJ-XXMLZKCSSA-N
• INCHI: 1S/C32H40O8/c1-18-14-24-23(30(24,5)6)12-13-31(17-37-31)29(38-20(3)33)26-27(39-25(35)15-22-10-8-7-9-11-22)19(2)16-32(26,28(18)36)40-21(4)34/h7-11,14,19,23-24,26-27,29H,12-13,15-17H2,1-6H3/b18-14+/t19-,23-,24+,26+,27-,29-,31+,32+/m0/s1
• Isomeric SMILES: C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)CC3=CC=CC=C3)[C@@H]([C@@]4(CC[C@H]5[C@H](C5(C)C)/C=C(/C2=O)\C)CO4)OC(=O)C)OC(=O)C
• Molecular Weight: 552.66
• Reaxy-Rn: 23498853
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=23498853&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Diterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Diterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Diterpenoids
• Alternative Parents: Tricarboxylic acids and derivatives Alpha-acyloxy ketones Benzene and substituted derivatives Ketones Carboxylic acid esters Oxacyclic compounds Epoxides Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Diterpenoid - Lathyrane diterpenoid - Tricarboxylic acid or derivatives - Alpha-acyloxy ketone - Monocyclic benzene moiety - Benzenoid - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Dialkyl ether - Oxacycle - Oxirane - Ether - Organoheterocyclic compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
• External Descriptors: Not available

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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

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

Associated Targets(non-human)

Cruzipain (33337 Activities)

Explore this target

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 21 mg/mL (37.99 mM)
• Sensitivity: light sensitive
• DMSO(mg / mL) Max Solubility: 21
• DMSO(mM) Max Solubility: 37.99804581
• Molecular Weight: 552.700 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 552.272 Da
• Monoisotopic Mass: 552.272 Da
• Topological Polar Surface Area: 109.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 1090.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1