Bruceantinol - ≥98% , CAS No.53729-52-5

CAS: 53729-52-5 Cat. No.: B649375 Molecular Weight: 606.6 PubChem CID: 5281305

GRADE & PURITY ≥98%

Synonyms

DTXSID70415102 | CHEBI:3189 | Q27105980 | AKOS040760307 | BRUCEANTINOL | E88745 | HY-N8146 | C08750 | MS-30670 | methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Bruceantinol, a quassinoid isolated from Brucea javanica , inhibits pepper mottle virus in pepper Bruceantinol is a STAT3 inhibitor demonstrating potent antitumor activity in in vitro and in vivo human colorectal cancer (CRC) models. Bruceantinol strongly inhibits STAT3 DNA-binding ability ( IC 50 =2.4 pM), blocks the constitutive and IL-6-induced STAT3 activation, and suppresses transcription of MCL-1 , PTTG1, survivin and c-Myc .

Form:Solid

IC50& Target:IC 50 : 2.4 pM (STAT3 DNA-binding ability)

Specifications

Synonyms

DTXSID70415102 | CHEBI:3189 | Q27105980 | AKOS040760307 | BRUCEANTINOL | E88745 | HY-N8146 | C08750 | MS-30670 | methyl (1R, 2S, 3R, 6R, 8R, 13S, 14R, 15R, 16S, 17S)-3-[(E)-4-acetyloxy-3, 4-dimethylpent-2-enoyl]oxy-10, 15, 16-trihydroxy-9, 13-dimethyl-4, 11-dioxo-5, 18-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Bruceantinol, a quassinoid isolated from Brucea javanica , inhibits pepper mottle virus in pepper. Bruceantinol is a STAT3 inhibitor demonstrating potent antitumor activity in in vitro and in vivo human colorectal cancer (CRC) models. Bruceantinol st

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: CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• IUPAC Name: methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate
• InChIKey: SREUSBYRKOPNJK-AJPRWBMOSA-N
• INCHI: 1S/C30H38O13/c1-12(27(4,5)43-14(3)31)8-18(33)42-21-23-29-11-40-30(23,26(38)39-7)24(36)20(35)22(29)28(6)10-16(32)19(34)13(2)15(28)9-17(29)41-25(21)37/h8,15,17,20-24,34-36H,9-11H2,1-7H3/b12-8+/t15-,17+,20+,21+,22+,23+,24-,28-,29+,30-/m0/s1
• Isomeric SMILES: CC1=C(C(=O)C[C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)(C)OC(=O)C)(OC5)C(=O)OC)O)O)C)O
• Alternate CAS: 53729-52-5
• PubChem CID: 5281305
• MeSH Entry Terms: bruceantinol;methyl (11beta,12alpha,15beta)-15-(((2E)-4-acetoxy-3,4-dimethyl-2-pentenoyl)oxy)-3,11,12-trihydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate;picras-3-en-21-oic acid, 15-(((2E)-4-(acetyloxy)-3,4-dimethyl-1-oxo-2-penten-1-yl)oxy)-13,20-epoxy-3
• Molecular Weight: 606.6

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: Quassinoids
• Alternative Parents: Triterpenoids Naphthopyrans Tetracarboxylic acids and derivatives Naphthalenes Furopyrans Beta hydroxy acids and derivatives Cyclohexenones Oxepanes Delta valerolactones Fatty acid esters Pyrans Oxanes Tetrahydrofurans Enoate esters Furans Methyl esters 1,2-diols Cyclic alcohols and derivatives Secondary alcohols Enols Dialkyl ethers Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpenoid - C-20 quassinoid skeleton - Quassinoid - Naphthopyran - Tetracarboxylic acid or derivatives - Naphthalene - Furopyran - Beta-hydroxy acid - Cyclohexenone - Fatty acid ester - Delta_valerolactone - Delta valerolactone - Oxepane - Pyran - Oxane - Fatty acyl - Hydroxy acid - Cyclic alcohol - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Furan - Methyl ester - Tetrahydrofuran - Ketone - 1,2-diol - Cyclic ketone - Lactone - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Oxacycle - Organoheterocyclic compound - Dialkyl ether - Enol - Ether - Polyol - Alcohol - Organic oxide - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
• External Descriptors: Dammarenes

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)

Explore this target

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

HCT-116 (91556 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

• Molecular Weight: 606.600 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 8
• Exact Mass: 606.231 Da
• Monoisotopic Mass: 606.231 Da
• Topological Polar Surface Area: 192.000 Ų
• Heavy Atom Count: 43
• Formal Charge: 0
• Complexity: 1360.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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

References

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