Brevilin A - ≥98% , CAS No.16503-32-5

CAS: 16503-32-5 Cat. No.: B413675 Molecular Weight: 346.42 EC Number: 111-884-3 PubChem CID: 12302076

GRADE & PURITY ≥98%

Synonyms

[(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate | AC-34175 | EKT624Z4TZ | Ambros-2-en-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone, 2-methylcrotonate, (Z)- |

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product description
Brevilin A (6-O-Angeloylplenolina), a sesquiterpene lactone isolated from Centipeda minima, is a selective inhibitor of STAT3 and attenuates the JAKs activity by blocking the JAKs tyrosine kinase domain JH1. Brevilin A induces apoptosis and autophagy of colon adenocarcinoma cell CT26 via mitochondrial pathway and PI3K/AKT/mTOR inactivation.
Targets：STAT3； JAK

Specifications

Synonyms

[(1S, 3aR, 5R, 5aR, 8aR, 9S, 9aR)-1, 5, 8a-trimethyl-2, 8-dioxo-3a, 4, 5, 5a, 9, 9a-hexahydro-1H-azuleno[6, 5-b]furan-9-yl] (Z)-2-methylbut-2-enoate | AC-34175 | EKT624Z4TZ | Ambros-2-en-12-oic acid, 6alpha, 8beta-dihydroxy-4-oxo-, 12, 8-lactone, 2-methylcrotonate, (Z)- |

Specifications & Purity

≥98%

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.

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC=C(C)C(=O)OC1C2C(C(=O)OC2CC(C3C1(C(=O)C=C3)C)C)C
• IUPAC Name: [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate
• InChIKey: KUPPZVXLWANEJJ-UXPPPGSFSA-N
• INCHI: 1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1
• Isomeric SMILES: C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H](C(=O)O[C@@H]2C[C@H]([C@H]3[C@]1(C(=O)C=C3)C)C)C
• PubChem CID: 12302076
• Molecular Weight: 346.42

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: Sesquiterpene lactones
• Alternative Parents: Ambrosanolides and secoambrosanolides Pseudoguaianes Fatty acid esters Gamma butyrolactones Dicarboxylic acids and derivatives Oxolanes Enoate esters Ketones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Helenalin-skeleton - Ambrosanolide - Pseudoguaiane sesquiterpenoid - Sesquiterpenoid - Fatty acid ester - Dicarboxylic acid or derivatives - Gamma butyrolactone - Fatty acyl - Oxolane - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Lactone - Ketone - Carboxylic acid ester - Oxacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids 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

Associated Targets(Human)

STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

Discover Target: STAT3

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

HCT-116 (91556 Activities)

Explore this target

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

HepG2 (196354 Activities)

Explore this target

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

Associated Targets(non-human)

Entamoeba histolytica (2676 Activities)

Explore this target

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

Influenza A virus (11224 Activities)

Explore this target

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

RAW264.7 (28094 Activities)

Explore this target

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: 69 mg/mL (199.18 mM)
• Molecular Weight: 346.400 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 346.178 Da
• Monoisotopic Mass: 346.178 Da
• Topological Polar Surface Area: 69.700 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 676.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• 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