N-(p-Amylcinnamoyl)anthranilic acid - Moligand™, ≥96% , Channel blocker of TRPC3;Channel blocker of TRPC6;Channel blocker of TRPM2;Channel blocker of TRPM8, CAS No.110683-10-8, Channel blocker of TRPC3;Channel blocker of TRPC6;Channel blocker of TRPM2;Channel blocker of TRPM8

CAS: 110683-10-8 Cat. No.: A275778 Molecular Weight: 337.4

GRADE & PURITY Moligand™, ≥96%

Synonyms

ACA - CAS 110683-10-8 | N-(4-Pentylcinnamoyl)anthranilic acid | N17081 | BRD-K77817104-001-01-3 | Benzoic acid, 2-((1-oxo-3-(4-pentylphenyl)-2-propenyl)amino)- | 2-(3-(4-Pentylphenyl)acrylamido)benzoic acid | Benzoic acid, 2-((1-oxo-3-(4-pentylphenyl)-2-p

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

 N-(p-Amylcinnamoyl) anthranilic Acid (ACA), a cell permeable inhibitor of PLA2, has been reported to inhibit α-ketoisocaproic acid and glyceraldehyde-induced insulin secretion, as well as glucose-induced insulin secretion. Additionally, by inhibiting PLA2, ACA consequentially suppresses glucose-induced arachidonic acid formation in cells. Furthermore, research has shown ACA to modulate the activity of different transient receptor potential channels. In particular, ACA's blocking ability of diacylglycerol-activated TRP channels is of special interest since it offers the opportunity to interfere with receptor-induced Ca2+-dependent signaling processes in vascular smooth muscle cells and platelets.

Specifications

Synonyms

ACA - CAS 110683-10-8 | N-(4-Pentylcinnamoyl)anthranilic acid | N17081 | BRD-K77817104-001-01-3 | Benzoic acid, 2-((1-oxo-3-(4-pentylphenyl)-2-propenyl)amino)- | 2-(3-(4-Pentylphenyl)acrylamido)benzoic acid | Benzoic acid, 2-((1-oxo-3-(4-pentylphenyl)-2-p

Specifications & Purity

Moligand™, ≥96%

Biochemical and Physiological Mechanisms

Phospholipases A2 (PLA 2 ) inhibitor. Modulates TRP ion channels. Reversibly inhibits Ca 2+ activated chloride current in a concentration-dependent manner (IC 50 = 4.2 μM). Inhibits insulin secretion. Cell permeable. Active in vivo and in vitro .

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

CHANNEL BLOCKER

Mechanism of action

Channel blocker of TRPC3;Channel blocker of TRPC6;Channel blocker of TRPM2;Channel blocker of TRPM8

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥96%

Names and Identifiers

• Pubchem Sid: 504763658
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763658
• Canonical Smiles: CCCCCC1=CC=C(C=C1)C=CC(=O)NC2=CC=CC=C2C(=O)O
• IUPAC Name: 2-[[(E)-3-(4-pentylphenyl)prop-2-enoyl]amino]benzoic acid
• InChIKey: GAMRBCZMOOMBSQ-CCEZHUSRSA-N
• INCHI: 1S/C21H23NO3/c1-2-3-4-7-16-10-12-17(13-11-16)14-15-20(23)22-19-9-6-5-8-18(19)21(24)25/h5-6,8-15H,2-4,7H2,1H3,(H,22,23)(H,24,25)/b15-14+
• Isomeric SMILES: CCCCCC1=CC=C(C=C1)/C=C/C(=O)NC2=CC=CC=C2C(=O)O
• Molecular Weight: 337.4
• Reaxy-Rn: 27868094
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27868094&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Cinnamic acids and derivatives
      • Subclass Cinnamic acid amides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Cinnamic acids and derivatives
• Subclass: Cinnamic acid amides
• Intermediate Tree Nodes: Not available
• Direct Parent: N-cinnamoylanthranilic acids
• Alternative Parents: Acylaminobenzoic acid and derivatives Benzoic acids Anilides Styrenes N-arylamides Benzoyl derivatives Vinylogous amides Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: N-cinnamoylanthranilic acid - Acylaminobenzoic acid or derivatives - Benzoic acid or derivatives - Benzoic acid - Anilide - Benzoyl - Styrene - N-arylamide - Monocyclic benzene moiety - Benzenoid - Vinylogous amide - Carboxamide group - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-cinnamoylanthranilic acids. These are aromatic compounds containing a cinnamic acid conjugated to an anthranilic acid.
• 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)

TRPM2 Tchem Transient receptor potential cation channel subfamily M member 2 (7 Activities)

Discover Target: TRPM2

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

TRPC3 Tchem Short transient receptor potential channel 3 (0 Activities)

Discover Target: TRPC3

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

TRPC6 Tchem Short transient receptor potential channel 6 (0 Activities)

Discover Target: TRPC6

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

TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (2 Activities)

Discover Target: TRPM8

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

SH-SY5Y (11521 Activities)

Explore this target

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

TRPM2 Tchem Transient receptor potential cation channel subfamily M member 2 (348 Activities)

Discover Target: TRPM2

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

Associated Targets(non-human)

PLA2G1B Phospholipase A2 group 1B (227 Activities)

Discover Target: PLA2G1B

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

Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

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

Trpm8 Transient receptor potential cation channel subfamily M member 8 (889 Activities)

Discover Target: Trpm8

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 100 mM and in ethanol to 100 mM (with heating)
• Molecular Weight: 337.400 g/mol
• XLogP3: 6.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 337.168 Da
• Monoisotopic Mass: 337.168 Da
• Topological Polar Surface Area: 66.400 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 452.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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