Arenobufagin - Moligand™, ≥98% , CAS No.464-74-4

CAS: 464-74-4 Cat. No.: A412643 Molecular Weight: 416.51

GRADE & PURITY Moligand™, ≥98%

Synonyms

Arenobufagin | 3,11,14-trihydroxy-12-oxo-bufa-20,22-dienolide | 5-((3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one | 5.beta.-Bufa-20,22-dienolide, 3.beta.,11.alpha.,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Arenobufagin is a natural bufadienolide from toad venom and induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway.

Specifications

Synonyms

Arenobufagin | 3, 11, 14-trihydroxy-12-oxo-bufa-20, 22-dienolide | 5-((3S, 5R, 8R, 9S, 10S, 11S, 13R, 14S, 17R)-3, 11, 14-trihydroxy-10, 13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one | 5.beta.-Bufa-20, 22-dienolide, 3.beta., 11.alpha.,

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Arenobufagin is a natural bufadienolide from toad venom and induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway.

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™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC12CCC(CC1CCC3C2C(C(=O)C4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O
• IUPAC Name: 5-[(3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxo-2,3,4,5,6,7,8,9,11,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one
• InChIKey: JGDCRWYOMWSTFC-AZGSIFHYSA-N
• INCHI: 1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,20+,22+,23+,24+/m1/s1
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2[C@@H](C(=O)[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O)O
• Molecular Weight: 416.51
• Reaxy-Rn: 39110815
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=39110815&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Steroid lactones

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Steroid lactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Bufanolides and derivatives
• Alternative Parents: Oxosteroids 3-beta-hydroxysteroids 14-hydroxysteroids 11-alpha-hydroxysteroids Pyranones and derivatives Tertiary alcohols Heteroaromatic compounds Secondary alcohols Lactones Ketones Cyclic alcohols and derivatives Polyols Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Bufanolide-skeleton - 3-hydroxysteroid - 14-hydroxysteroid - Hydroxysteroid - 12-oxosteroid - Oxosteroid - 11-alpha-hydroxysteroid - 11-hydroxysteroid - 3-beta-hydroxysteroid - Pyranone - Pyran - Tertiary alcohol - Heteroaromatic compound - Cyclic alcohol - Secondary alcohol - Ketone - Lactone - Polyol - Oxacycle - Organoheterocyclic compound - Alcohol - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.
• 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)

MCF7 (126967 Activities)

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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

MDA-MB-435 (38290 Activities)

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Associated Targets(non-human)

Mus musculus (284745 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: 83 mg/mL (199.27 mM); Water: Insoluble; Ethanol: 10 mg/mL
• Molecular Weight: 416.500 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 416.22 Da
• Monoisotopic Mass: 416.22 Da
• Topological Polar Surface Area: 104.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 847.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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