Cytochalasin D - ≥98% , CAS No.22144-77-0

CAS: 22144-77-0 Cat. No.: C102396 Peso molecular: 507.62 Beilstein Registry Number: 1632828 Número EC: 244-804-1

GRADE & PURITY ≥98%

Synonyms

Lygosporin A | MFCD00077706 | SY9F0FZ3TO | NSC209835 | Zygosporin A | (7S,13E,16S,18R,19E,21R)-21-(Acetyloxy)- 7,18-dihydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,17-dione

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

Cytochalasin D is a cell permeable mycotoxin, which causes both the association and dissociation of actin subunits. Cytochalasin D disrupts actin filaments and inhibits actin polymerization.
Cytochalasins are used as tools in cytological research, and in the field of actin polymerization. Cytochalasin D is 10 times more effective than cytochalasin B and does not inhibit glucose transport across cell membranes.

Specifications

Sinónimos

Lygosporin A | MFCD00077706 | SY9F0FZ3TO | NSC209835 | Zygosporin A | (7S, 13E, 16S, 18R, 19E, 21R)-21-(Acetyloxy)- 7, 18-dihydroxy-16, 18-dimethyl-10-phenyl[11]cytochalasa-6(12), 13, 19-triene-1, 17-dione

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

Potent actin polymerization inhibitor. Binds to G- and F-actin. Stimulates actin depolymerization. Induces cell cycle arrest at G1-S. Activates p53-dependent pathways. Cell permeable.

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Nota

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.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: 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
• Isómeros 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 Alemania: 3
• RTECS: GZ4850000
• Número ONU: 3172
• Grupo de embalaje: I
• Peso molecular: 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
    • Clase Cytochalasans

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

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

Jurkat (10389 Activities)

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SW-620 (52400 Activities)

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

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

Discover Target: TLR2

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

Objetivos asociados (no humanos)

H4 (48 Activities)

Explore this target

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

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Balamuthia mandrillaris (26 Activities)

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

ABC1 ATP binding cassette transporter Abc1p (50 Activities)

Discover Target: ABC1

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

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: DMSO, Ethanol, Methanol
• Sensibilidad: Moisture sensitive;Light sensitive
• Peso molecular: 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

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