Ebelactone A - Moligand™, ≥98% , CAS No.76808-16-7

CAS: 76808-16-7 Cat. No.: E329503 Formula: C₂₀H₃₄O₄ Molecular Weight: 338.48

GRADE & PURITY Moligand™, ≥98%

Synonyms

Ebelactone A microbial | NSC335650 | NSC-335650 | SCHEMBL10021628 | (3S,4S)-4-[(E,2S,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one | ebelactone a | (E)-4-(9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl)-3-met

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Ebelactone A is a β-lactone enzyme inhibitor that was first isolated from a cultured strain of soil actinomycetes. It can inhibit esterases, lipases, and N-formylmethionine aminopeptidases (IC50s = 0.056, 0.003, and 0.08 µg/ml, respectively) found on cell surfaces, which has been shown to stimulate host defense in immune cells. Ebelactone A is also reported to inhibit cutinases produced by fungal pathogens, thus demonstrating a plant-protective function.

Specifications

Synonyms

Ebelactone A microbial | NSC335650 | NSC-335650 | SCHEMBL10021628 | (3S,4S)-4-[(E,2S,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one | ebelactone a | (E)-4-(9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl)-3-met

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C,Argon charged

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

Purity

≥98%

Names and Identifiers

Canonical Smiles

CCC(C)C(C(C)C(=O)C(C)C=C(C)CC(C)C1C(C(=O)O1)C)O

IUPAC Name

4-[(E)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one

InChIKey

WOISDAHQBUYEAF-PKNBQFBNSA-N

INCHI

1S/C20H34O4/c1-8-12(3)17(21)15(6)18(22)13(4)9-11(2)10-14(5)19-16(7)20(23)24-19/h9,12-17,19,21H,8,10H2,1-7H3/b11-9+

Isomeric SMILES

CCC(C)C(C(C)C(=O)C(C)/C=C(\C)/CC(C)C1C(C(=O)O1)C)O

WGK Germany

3

RTECS

RQ7730000

Molecular Weight

338.48

Reaxy-Rn

26177513

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26177513&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Terpene lactones
• Alternative Parents: Sesquiterpenoids Fatty alcohols Beta-hydroxy ketones Beta propiolactones Secondary alcohols Oxetanes Carboxylic acid esters Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Terpene lactone - Sesquiterpenoid - Fatty alcohol - Beta-hydroxy ketone - Fatty acyl - Beta_propiolactone - Carboxylic acid ester - Ketone - Secondary alcohol - Oxetane - Lactone - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Alcohol - Carbonyl group - Organic oxygen compound - Organooxygen compound - Organic oxide - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
• 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

Chemical and Physical Properties

• Solubility: Soluble in water (partly), methanol (10 mg/ml), ethanol, and chloroform.
• x_refractive_index: n20D1.48 (Predicted)
• x_boil_point_char: ~462.8° C at 760 mmHg (Predicted)
• x_melt_point_char: 128.07° C (Predicted)
• Molecular Weight: 338.500 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 338.246 Da
• Monoisotopic Mass: 338.246 Da
• Topological Polar Surface Area: 63.600 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 482.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 7
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1