CP 640186 - Moligand™, ≥98% , Inhibitor of Acetyl-CoA carboxylase 1;Inhibitor of Acetyl-CoA carboxylase 2, CAS No.591778-68-6, Inhibitor of Acetyl-CoA carboxylase 1;Inhibitor of Acetyl-CoA carboxylase 2

CAS: 591778-68-6 Cat. No.: C413618 Molecular Weight: 485.62

GRADE & PURITY Moligand™, ≥98%

Synonyms

AKOS027254693 | 1w2x | CC3 | (Anthracen-9-yl)((3R)-3-((morpholin-4-yl)carbonyl)(1,4')bipiperidinyl-1'-yl)methanone | CHEBI:45293 | (3R)-1'-(ANTHRACENE-9-CARBONYL)-3-(MORPHOLINE-4-CARBONYL)-1,4'-BIPIPERIDINE | RCP | EN300-18161237 | LDQKDRLEMKIYMC-XMMPIXPA

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

CP 640186 CP 640186 is an isozyme-nonselective ACC (Acetyl-CoA carboxylase) inhibitor with IC50 values of 53 and 61 nM for rat liver ACC1 and rat skeletal muscle ACC2, respectively.

Targets

ACC 55 nM

In vitro

CP-610431 inhibited ACC1 and ACC2 with IC50s of ∼50 nm. Inhibition was reversible, uncompetitive with respect to ATP, and non-competitive with respect to bicarbonate, acetyl-CoA, and citrate. CP-610431 also inhibited fatty acid synthesis, triglyceride (TG) synthesis, TG secretion, and apolipoprotein B secretion in HepG2 cells (ACC1) with EC50s of 1.6, 1.8, 3.0, and 5.7 μM, without affecting either cholesterol synthesis or apolipoprotein CIII secretion. It also inhibited both isozymes with IC50s of ∼55 nM in inhibiting HepG2 cell fatty acid and TG synthesis. CP-610431 stimulated fatty acid oxidation in C2C12 cells (ACC2) and in rat epitrochlearis muscle strips with EC50s of 57 nM and 1.3 μM.

In vivo

In rats, CP-640186 lowered hepatic, soleus muscle, quadriceps muscle, and cardiac muscle malonyl-CoA with ED50s of 55, 6, 15, and 8 mg/kg. Consequently, CP-640186 inhibited fatty acid synthesis in rats, CD1 mice, and ob/ob mice with ED50s of 13, 11, and 4 mg/kg, and stimulated rat whole body fatty acid oxidation with an ED50 of ∼30 mg/kg. Pharmacokinetic evaluation of CP-640186 in male Sprague-Dawley rats (intravenous dose, 5 mg/kg; oral dose, 10 mg/kg) yielded a plasma half-life of 1.5 h, a bioavailability of 39%, a Clp of 65 ml/min/kg, a Vdss of 5 liters/kg, an oral Tmax of 1.0 h, an oral Cmax of 345 ng/ml, and an oral AUC0-∞ of 960 ng·h/ml. At the same dose level, pharmacokinetic evaluation of CP-640186 in ob/ob mice yielded a plasma half-life of 1.1 h, a bioavailability of 50%, a Clp of 54 ml/min/kg, an oral Tmax of 0.25 h, an oral Cmax of 2177 ng/ml, and an oral AUC0-∞ of 3068 ng·h/ml.

Specifications

Synonyms

AKOS027254693 | 1w2x | CC3 | (Anthracen-9-yl)((3R)-3-((morpholin-4-yl)carbonyl)(1, 4')bipiperidinyl-1'-yl)methanone | CHEBI:45293 | (3R)-1'-(ANTHRACENE-9-CARBONYL)-3-(MORPHOLINE-4-CARBONYL)-1, 4'-BIPIPERIDINE | RCP | EN300-18161237 | LDQKDRLEMKIYMC-XMMPIXPA

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

CP 640186 is an isozyme-nonselective ACC (Acetyl-CoA carboxylase) inhibitor with IC50 values of 53 and 61 nM for rat liver ACC1 and rat skeletal muscle ACC2, respectively.

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

Inhibitor of Acetyl-CoA carboxylase 1;Inhibitor of Acetyl-CoA carboxylase 2

Purity

≥98%

Product Properties

• ALogP: 2.88
• hba_count: 3
• Rotatable Bond: 3

Names and Identifiers

• Pubchem Sid: 504758884
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758884
• Canonical Smiles: C1CC(CN(C1)C2CCN(CC2)C(=O)C3=C4C=CC=CC4=CC5=CC=CC=C53)C(=O)N6CCOCC6
• IUPAC Name: [(3R)-1-[1-(anthracene-9-carbonyl)piperidin-4-yl]piperidin-3-yl]-morpholin-4-ylmethanone
• InChIKey: LDQKDRLEMKIYMC-XMMPIXPASA-N
• INCHI: 1S/C30H35N3O3/c34-29(32-16-18-36-19-17-32)24-8-5-13-33(21-24)25-11-14-31(15-12-25)30(35)28-26-9-3-1-6-22(26)20-23-7-2-4-10-27(23)28/h1-4,6-7,9-10,20,24-25H,5,8,11-19,21H2/t24-/m1/s1
• Isomeric SMILES: C1C[C@H](CN(C1)C2CCN(CC2)C(=O)C3=C4C=CC=CC4=CC5=CC=CC=C53)C(=O)N6CCOCC6
• Molecular Weight: 485.62
• Reaxy-Rn: 14183663
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=14183663&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Anthracenes
      • Subclass Anthracenecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Anthracenes
• Subclass: Anthracenecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracenecarboxylic acids and derivatives
• Alternative Parents: N-benzoylpiperidines Naphthalenecarboxamides Piperidinecarboxamides Aminopiperidines Morpholines Tertiary carboxylic acid amides Trialkylamines Amino acids and derivatives Oxacyclic compounds Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracene carboxylic acid or derivatives - N-benzoylpiperidine - 1-naphthalenecarboxamide - 1-naphthalenecarboxylic acid or derivatives - N-acyl-piperidine - Piperidinecarboxamide - 3-piperidinecarboxamide - 4-aminopiperidine - Morpholine - Piperidine - Oxazinane - Tertiary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Organic nitrogen compound - Amine - Organic oxide - Hydrocarbon derivative - Organopnictogen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracenecarboxylic acids and derivatives. These are organic compounds containing a carboxylic acid group (or a derivative thereof) attached to an anthracene ring system.
• External Descriptors: N-acylpiperidine - morpholines - anthracenes - bipiperidines

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)

ACACB Tchem Acetyl-CoA carboxylase 2 (6 Activities)

Discover Target: ACACB

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACACA Tchem Acetyl-CoA carboxylase 1 (5 Activities)

Discover Target: ACACA

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACACA Tchem Acetyl-CoA carboxylase 1 (794 Activities)

Discover Target: ACACA

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

ACACB Tchem Acetyl-CoA carboxylase 2 (3474 Activities)

Discover Target: ACACB

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

HepG2 (196354 Activities)

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

Liver microsomes (16955 Activities)

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

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

Rattus norvegicus (775804 Activities)

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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

Acetyl-Coenzyme A carboxylase 2 (5 Activities)

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

ACCase Acetyl-CoA carboxylase (4 Activities)

Discover Target: ACCase

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

SARS-CoV-2 (38078 Activities)

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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: 97 mg/mL (199.74 mM); Ethanol: 97 mg/mL (199.74 mM); Water: Insoluble
• DMSO(mg / mL) Max Solubility: 97
• DMSO(mM) Max Solubility: 199.744656315638
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 485.600 g/mol
• XLogP3: 4.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 485.268 Da
• Monoisotopic Mass: 485.268 Da
• Topological Polar Surface Area: 53.100 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 753.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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