Cytochalasin D - Ready Made Solution, from Zygosporium mansonii, 5mg/mL in DMSO , CAS No.22144-77-0

CAS: 22144-77-0 Cat. No.: C477743 Formula: C₃₀H₃₇NO₆ Molecular Weight: 507.62 Beilstein Registry Number: 1632828 EC Number: 244-804-1

GRADE & PURITY Ready Made Solution, from Zygosporium mansonii, 5mg/mL in DMSO

Synonyms

AKOS030213128 | F82057 | 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6-12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)- | HSDB 3549 | Lygosporin A | E

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Description

Cytochalasin B is used to inhibit sugar transport in fibroblasts , decrease cytoskeletal actin and myosin in rabbit neutrophils , and to stimulate B lymphocytes . It is a potent inhibitor of actin polymerization, disrupts actin microfilaments, activates the p53-dependent pathways, inhibits smooth muscle contraction, and inhibits insulin-stimulated glucose transport.

Specifications

Synonyms

AKOS030213128 | F82057 | 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6-12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)- | HSDB 3549 | Lygosporin A | E

Specifications & Purity

Ready Made Solution, from Zygosporium mansonii, 5mg/mL in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Names and Identifiers

Pubchem Sid

528774593

Canonical Smiles

CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O

IUPAC Name

[(1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

InChIKey

SDZRWUKZFQQKKV-JHADDHBZSA-N

INCHI

1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17-18,22-26,33,36H,3,10,16H2,1-2,4-5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,22-,23-,24+,25-,26+,29+,30+/m0/s1

Isomeric SMILES

C[C@H]1C/C=C/[C@H]2[C@@H](C(=C)[C@H]([C@@H]3[C@@]2([C@@H](/C=C/[C@@](C1=O)(C)O)OC(=O)C)C(=O)N[C@H]3CC4=CC=CC=C4)C)O

WGK Germany

3

RTECS

GZ4850000

UN Number

3172

Packing Group

I

Molecular Weight

507.62

Beilstein

1632828

Reaxy-Rn

25133796

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25133796&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cytochalasans
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cytochalasans
• Alternative Parents: Isoindolones Isoindoles Acyloins Benzene and substituted derivatives Pyrrolidine-2-ones Tertiary alcohols Secondary carboxylic acid amides Secondary alcohols Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Lactams Azacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Carbocyclic cytochalasan skeleton - Cytochalasan - Isoindolone - Isoindoline - Isoindole - Isoindole or derivatives - Acyloin - Monocyclic benzene moiety - Benzenoid - Pyrrolidone - 2-pyrrolidone - Cyclic alcohol - Pyrrolidine - Tertiary alcohol - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Cyclic ketone - Ketone - Lactam - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.
• 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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

Ramos (1218 Activities)

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Jurkat (10389 Activities)

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SW-620 (52400 Activities)

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TLR2 Tchem Toll-like receptor 1/2 (401 Activities)

Discover Target: TLR2

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Associated Targets(non-human)

H4 (48 Activities)

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BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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Balamuthia mandrillaris (26 Activities)

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ABC1 ATP binding cassette transporter Abc1p (50 Activities)

Discover Target: ABC1

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 507.600 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 507.262 Da
• Monoisotopic Mass: 507.262 Da
• Topological Polar Surface Area: 113.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 996.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1