β-Elemonic acid - 10mM in DMSO , CAS No.28282-25-9

CAS: 28282-25-9 Cat. No.: E422990 Molecular Weight: 454.68 EC Number: 805-141-9

GRADE & PURITY 10mM in DMSO

Synonyms

BETA-ELEMONICACID | BDBM50039667 | (2S)-6-methyl-2-[(5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid | b-Elemonic acid | AKOS016036180 | Elemonic acid | 3-Oxotirucalleno

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Application:

β-Elemonic acid is a triterpene isolated from Boswellia that exhibits anticancer activity. It inhibits growth of non-small cell lung cancer (NSCLC) A549 cells (IC50 = 6.92 µM) in vitro. β-Elemonic acid induces apoptosis and cytotoxicity in A549 cells in a dose-dependent manner but has no effect on normal epithelial WI-38 cells. It inhibits phosphorylation of p42/44, MAPK/JNK, and p38 and induces production of reactive oxygen species (ROS) and COX-2 expression in vitro. β-Elemonic acid also inhibits prolyl endopeptidase (IC50 = 39.74 µM) in vitro.

Specifications

Synonyms

BETA-ELEMONICACID | BDBM50039667 | (2S)-6-methyl-2-[(5R, 10S, 13S, 14S, 17S)-4, 4, 10, 13, 14-pentamethyl-3-oxo-1, 2, 5, 6, 7, 11, 12, 15, 16, 17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid | b-Elemonic acid | AKOS016036180 | Elemonic acid | 3-Oxotirucalleno

Specifications & Purity

10mM in DMSO

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

• Canonical Smiles: CC(=CCCC(C1CCC2(C1(CCC3=C2CCC4C3(CCC(=O)C4(C)C)C)C)C)C(=O)O)C
• IUPAC Name: (2S)-6-methyl-2-[(5R,10S,13S,14S,17S)-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,7,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]hept-5-enoic acid
• InChIKey: XLPAINGDLCDYQV-SDTWUMECSA-N
• INCHI: 1S/C30H46O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,28+,29-,30+/m0/s1
• Isomeric SMILES: CC(=CCC[C@@H]([C@@H]1CC[C@]2([C@]1(CCC3=C2CC[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)C)C)C(=O)O)C
• Molecular Weight: 454.68
• Reaxy-Rn: 42764299
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=42764299&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Triterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Triterpenoids
• Alternative Parents: Bile acids, alcohols and derivatives Steroid acids 3-oxo-5-alpha-steroids Medium-chain fatty acids Unsaturated fatty acids Cyclic ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Triterpenoid - Bile acid, alcohol, or derivatives - Steroid acid - 3-oxosteroid - Oxosteroid - 3-oxo-5-alpha-steroid - Steroid - Medium-chain fatty acid - Fatty acyl - Fatty acid - Unsaturated fatty acid - Ketone - Cyclic ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six 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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 454.700 g/mol
• XLogP3: 7.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 454.345 Da
• Monoisotopic Mass: 454.345 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 33
• Formal Charge: 0
• Complexity: 904.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• 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