ETC-1002 - Moligand™, ≥99% , ATP-citrate synthase inhibitor, CAS No.738606-46-7, ATP-citrate synthase inhibitor

CAS: 738606-46-7 Cat. No.: E413887 Molecular Weight: 344.49 EC Number: 810-485-8

GRADE & PURITY Moligand™, ≥99%

Synonyms

acido bempedoico | CHEBI:44212 | DB11936 | (2R,3R)-rel-2,3-Dihydroxysuccinic acid | A905695 | AS-49804 | EINECS 207-354-7 | Epitope ID:115015 | s7953 | acidum bempedoicum | AMY31933 | BEMPEDOIC ACID [USAN] | CCG-267969 | bempedoic-acid | Q27075007 | BEMPE

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

ETC-1002 ETC-1002 (Bempedoic acid, ESP-55016),also known as Bempedoic acid, is an orally available, once-daily LDL-C lowering small molecule designed to lower elevated levels of LDL-C and to avoid side effects associated with existing LDL-C lowering therapies.ETC-1002 is an activator of hepatic AMP-activated protein kinase (AMPK) . It has potent inhibitory activity against hepatic ATP-citrate lyase (IC50=29 uM).

Targets

AMPK

In vitro

ETC-1002 is a new investigational low density lipoprotein cholesterol (LDL-C)-lowering agent which is a dicarboxylic acid derivative with a novel mechanism of action targeting two hepatic enzymes--adenosine triphosphate-citrate lyase (ACL) and adenosine monophosphate-activated protein kinase (AMPK), inhibiting sterol and fatty acid synthesis and promoting mitochondrial long-chain fatty acid oxidation. It increases levels of AMP-activated protein kinase (AMPK) phosphorylation, reduces activity of MAP kinases and decreases production of proinflammatory cytokines and chemokines. These effects on soluble mediators of inflammation can be significantly abrogated by LKB1 siRNAs, indicating that ETC-1002 activates AMPK and exerts its anti-inflammatory effects via an LKB1-dependent mechanism.

In vivo

ETC-1002 suppresses thioglycollate-induced homing of leukocytes into mouse peritoneal cavity. Similarly, in a mouse model of diet-induced obesity, ETC-1002 restores adipose AMPK activity, reduces JNK phosphorylation, and diminishes expression of macrophage-specific marker 4F/80. ETC-1002 is an inactive prodrug and converted to an active ACL inhibitor(ECT-1002-CoA) by endogenous liver ACS activity in vivo.

Cell Research(from reference)

Cell lines：Primary rat hepatocytes and differentiated human monocyte-derived macrophages 

Concentrations：30 μM or 100 μM 

Incubation Time：12 h 

Application

Bempedoic Acid is used for the treatment of dyslipidemia and other cardio-metabolic risk factors . It inhibits ATP citrate lyase (ACL), which an enzyme involved in fatty acid and cholesterol synthesis.

Specifications

Synonyms

acido bempedoico | CHEBI:44212 | DB11936 | (2R, 3R)-rel-2, 3-Dihydroxysuccinic acid | A905695 | AS-49804 | EINECS 207-354-7 | Epitope ID:115015 | s7953 | acidum bempedoicum | AMY31933 | BEMPEDOIC ACID [USAN] | CCG-267969 | bempedoic-acid | Q27075007 | BEMPE

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

ETC-1002 (Bempedoic acid, ESP-55016), also known as Bempedoic acid, is an orally available, once-daily LDL-C lowering small molecule designed to lower elevated levels of LDL-C and to avoid side effects associated with existing LDL-C lowering therapies.ETC-

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

INHIBITOR

Mechanism of action

ATP-citrate synthase inhibitor

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504765489
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765489
• Canonical Smiles: CC(C)(CCCCCC(CCCCCC(C)(C)C(=O)O)O)C(=O)O
• IUPAC Name: 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid
• InChIKey: HYHMLYSLQUKXKP-UHFFFAOYSA-N
• INCHI: 1S/C19H36O5/c1-18(2,16(21)22)13-9-5-7-11-15(20)12-8-6-10-14-19(3,4)17(23)24/h15,20H,5-14H2,1-4H3,(H,21,22)(H,23,24)
• Isomeric SMILES: CC(C)(CCCCCC(CCCCCC(C)(C)C(=O)O)O)C(=O)O
• Molecular Weight: 344.49
• Reaxy-Rn: 11997099
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11997099&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty acids and conjugates

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty acids and conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Long-chain fatty acids
• Alternative Parents: Methyl-branched fatty acids Hydroxy fatty acids Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Long-chain fatty acid - Methyl-branched fatty acid - Hydroxy fatty acid - Branched fatty acid - Dicarboxylic acid or derivatives - Secondary alcohol - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
• 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(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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: 68 mg/mL (197.39 mM); Water: Insoluble; Ethanol: Insoluble
• Melt Point(°C): 87 - 92°C
• Molecular Weight: 344.500 g/mol
• XLogP3: 4.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 344.256 Da
• Monoisotopic Mass: 344.256 Da
• Topological Polar Surface Area: 94.800 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 351.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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