Chaetoglobosin A - ≥98% , CAS No.50335-03-0

CAS: 50335-03-0 Cat. No.: C275299 Molecular Weight: 528.64 EC Number: 813-006-0

GRADE & PURITY ≥98%

Synonyms

Chaetoglobosin A | MLS000876953 | BRN 1097707 | SMR000440607 | 73AYL68TNX | ACon1_002056 | Q15410885 | MEGxm0_000025 | REGID_for_CID_6438437 | DTXSID20891790 | OUMWCYMRLMEZJH-VOXRAUTJSA- | HY-N6744 | LMPK11000003 | (13)Cytochalasa-13,17,21-triene-1,20,23-

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. It is important to note that this product is reported to be light sensitive. Store In the Dark. Store under desiccating conditions.

Specifications

Synonyms

Chaetoglobosin A | MLS000876953 | BRN 1097707 | SMR000440607 | 73AYL68TNX | ACon1_002056 | Q15410885 | MEGxm0_000025 | REGID_for_CID_6438437 | DTXSID20891790 | OUMWCYMRLMEZJH-VOXRAUTJSA- | HY-N6744 | LMPK11000003 | (13)Cytochalasa-13, 17, 21-triene-1, 20, 23-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Antibiotic agent. Phytotoxin. Cytochalasin analog . Targets filamentous actin and induces apoptosis. Shows cytotoxic effects against cancer cell lines. Shows antibacterial and nematicidal effects.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1CC=CC2C3C(O3)(C(C4C2(C(=O)C=CC(=O)C(C(=C1)C)O)C(=O)NC4CC5=CNC6=CC=CC=C65)C)C
• IUPAC Name: (1R,3E,6R,7E,9S,11E,13R,14S,16R,17S,18R,19S)-6-hydroxy-19-(1H-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.01,18.014,16]henicosa-3,7,11-triene-2,5,21-trione
• InChIKey: OUMWCYMRLMEZJH-VOXRAUTJSA-N
• INCHI: 1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37H,8,15H2,1-4H3,(H,34,38)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1
• Isomeric SMILES: C[C@H]\1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@@]2(C(=O)/C=C/C(=O)[C@@H](/C(=C1)/C)O)C(=O)N[C@H]4CC5=CNC6=CC=CC=C65)C)C
• Molecular Weight: 528.64
• Reaxy-Rn: 1097707
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1097707&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Cytochalasans
      • Subclass Chaetoglobosins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cytochalasans
• Subclass: Chaetoglobosins
• Intermediate Tree Nodes: Not available
• Direct Parent: Chaetoglobosins
• Alternative Parents: Macrolactams 3-alkylindoles Isoindolones Oxepanes Substituted pyrroles Pyrrolidine-2-ones Benzenoids Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Cyclic ketones Lactams Oxacyclic compounds Azacyclic compounds Dialkyl ethers Epoxides Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Chaetoglobosin skeleton - Macrolactam - Isoindolone - 3-alkylindole - Indole - Indole or derivatives - Isoindoline - Isoindole or derivatives - Oxepane - Benzenoid - Substituted pyrrole - 2-pyrrolidone - Pyrrolidone - Heteroaromatic compound - Pyrrole - Pyrrolidine - Cyclic ketone - Carboxamide group - Ketone - Lactam - Secondary carboxylic acid amide - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Ether - Oxirane - Dialkyl ether - Azacycle - Carboxylic acid derivative - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Alcohol - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as chaetoglobosins. These are cytochalasans with a structure in which the hydrogenated isoindole bears an (indol-3-yl)methyl group.
• External Descriptors: Cytochalasins

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)

HepG2 (196354 Activities)

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

Associated Targets(non-human)

Artemia salina (1320 Activities)

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Bacillus subtilis (32866 Activities)

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Rhizomucor miehei (120 Activities)

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Amorphotheca resinae (75 Activities)

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P388 (20296 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO to 10 mM
• Sensitivity: light sensitive
• Molecular Weight: 528.600 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 528.262 Da
• Monoisotopic Mass: 528.262 Da
• Topological Polar Surface Area: 112.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 1140.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 3
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 3
• Covalently-Bonded Unit Count: 1