Bruceine D - Moligand™, ≥98% , CAS No.21499-66-1

CAS: 21499-66-1 Cat. No.: B303049 Molecular Weight: 410.42

GRADE & PURITY Moligand™, ≥98%

Synonyms

AKOS037515227 | Bruceine D | AC1L9BNP | (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-Pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione | (1beta,11beta,12alpha,15beta)-1,11,12,14,15-pentahydroxy-1

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Bruceine D is a Notch inhibitor with anti-cancer activity and induces apoptosis in several human cancer cells. Bruceine D is an effective botanical insect antifeedant with outstanding systemic properties, causing potent pest growth inhibitory activity. Bruceine D has strong anthelmintic activity against D. intermedius with an EC50 value of 0.57 mg/L.

Specifications

Synonyms

AKOS037515227 | Bruceine D | AC1L9BNP | (1R, 2R, 3R, 6R, 8S, 12S, 13S, 14R, 15R, 16S, 17R)-2, 3, 12, 15, 16-Pentahydroxy-9, 13, 17-trimethyl-5, 18-dioxapentacyclo[12.5.0.01, 6.02, 17.08, 13]nonadec-9-ene-4, 11-dione | (1beta, 11beta, 12alpha, 15beta)-1, 11, 12, 14, 15-pentahydroxy-1

Specifications & Purity

Moligand™, ≥98%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4(C(C(=O)O3)O)O)(OC5)C)O)O)C)O
• IUPAC Name: (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-pentahydroxy-9,13,17-trimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione
• InChIKey: JBDMZGKDLMGOFR-KQSRGDCESA-N
• INCHI: 1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20+/m0/s1
• Isomeric SMILES: CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@]4([C@H](C(=O)O3)O)O)(OC5)C)O)O)C)O
• Molecular Weight: 410.42
• Reaxy-Rn: 25990591
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25990591&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: Quassinoids
• Alternative Parents: Triterpenoids Naphthopyrans Naphthalenes Furopyrans Cyclohexenones Delta valerolactones Oxepanes Pyrans Oxanes Tetrahydrofurans Tertiary alcohols Furans Secondary alcohols Carboxylic acid esters Cyclic alcohols and derivatives Monocarboxylic acids and derivatives Dialkyl ethers Polyols Oxacyclic compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Polycyclic triterpenoid - Triterpenoid - C-20 quassinoid skeleton - Quassinoid - Naphthopyran - Naphthalene - Furopyran - Delta valerolactone - Cyclohexenone - Delta_valerolactone - Oxepane - Oxane - Pyran - Tetrahydrofuran - Tertiary alcohol - Cyclic alcohol - Furan - Secondary alcohol - Carboxylic acid ester - Cyclic ketone - Ketone - Lactone - Carboxylic acid derivative - Ether - Dialkyl ether - Polyol - Monocarboxylic acid or derivatives - Oxacycle - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Organooxygen compound - Alcohol - 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)

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PANC-1 (6144 Activities)

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MDA-MB-231 (73002 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Molecular Weight: 410.400 g/mol
• XLogP3: -2.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 0
• Exact Mass: 410.158 Da
• Monoisotopic Mass: 410.158 Da
• Topological Polar Surface Area: 154.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 855.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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