Cytochalasin B - Moligand™, ≥98% , CAS No.14930-96-2

CAS: 14930-96-2 Cat. No.: C113160 Formula: C₂₉H₃₇NO₅ Peso molecolare: 479.61 Beilstein Registry Number: 1096207 Numero EC: 239-000-2

GRADE & PURITY Moligand™, ≥98%

Synonyms

C19954 | IDI1_034070 | MLS002703001 | SCHEMBL9046718 | 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)- | BDBM

Storage

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

Shipped In

Ice chest + Ice pads

Panoramica

Cytochalasin B is used in actin polymerization studies and cytological research. Cytochalasin B is a metabolite of the fungus Drechslera dematoidea which binds to the barbed end of actin filaments resulting in inhibition of both the association and dissociation of subunits. As opposed to other Cytochalasins, cytochalasin A and Cytochalasin B bind to the glucose transporter and inhibit monosaccharide transport across the plasma membrane. Cytochalasin B inhibits phagocytosis by both mononuclear phagocytes and polymorphonuclear leukocytes
A cell-permeable fungal toxin used in actin polymerization studies and cytological

Specifications

Sinonimi

C19954 | IDI1_034070 | MLS002703001 | SCHEMBL9046718 | 2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)- | BDBM

Specifiche e purezza

Moligand™, ≥98%

Meccanismi biochimici e fisiologici

One of a group of fungal metabolites that interfere with a wide variety of cellular movements. Useful tool for characterizing some of the polymerization properties of actin, and in studies on cytokinesis. Probe for the two hexose-transport systems in rat

Condizioni di conservazione di stoccaggio

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

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Grado

Moligand™

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.

Purezza

≥98%

Nomi e identificatori

• Pubchem Sid: 528774592
• Sorrisi canonici: CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
• IUPAC Name: (1S,4E,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
• InChIKey: GBOGMAARMMDZGR-TYHYBEHESA-N
• INCHI: 1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,22-24,26-27,31,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• Isomeri SMILES: C[C@@H]1CCC[C@H](/C=C/C(=O)O[C@]23[C@@H](/C=C/C1)[C@@H](C(=C)[C@H]([C@H]2[C@@H](NC3=O)CC4=CC=CC=C4)C)O)O
• WGK Germania: 3
• RTECS: RO0205000
• Numero UN: 1544
• Peso molecolare: 479.61
• Beilstein: 1096207
• Reaxy-Rn: 949535
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=949535&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Classe Cytochalasans
      • Subclass Cytochalasins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Classe: Cytochalasans
• Subclass: Cytochalasins
• Intermediate Tree Nodes: Not available
• Direct Parent: Cytochalasins
• Alternative Parents: Isoindolones Isoindoles Benzene and substituted derivatives Pyrrolidine-2-ones Enoate esters Secondary carboxylic acid amides Cyclic alcohols and derivatives Secondary alcohols Lactams Lactones Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Lactone cytochalasin skeleton - Cytochalasin - Isoindolone - Isoindoline - Isoindole - Isoindole or derivatives - Monocyclic benzene moiety - Pyrrolidone - Benzenoid - 2-pyrrolidone - Cyclic alcohol - Pyrrolidine - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Azacycle - Monocarboxylic acid or derivatives - Organopnictogen compound - Organic oxygen compound - Alcohol - Organonitrogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cytochalasins. These are cytochalasans in which the hydrogenated isoindolone bears a benzyl 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

Obiettivi associati (umani)

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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MAOB Tclin Monoamine oxidase B (8835 Activities)

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ITGAL Tclin Leukocyte adhesion glycoprotein LFA-1 alpha (170 Activities)

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SLC2A1 Tchem Glucose transporter (14755 Activities)

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A498 (42825 Activities)

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HL-60 (67320 Activities)

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MCF7 (126967 Activities)

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SK-MEL-2 (46422 Activities)

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SK-OV-3 (52876 Activities)

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XF498 (12972 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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HCT-15 (51914 Activities)

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SLC2A3 Tchem Solute carrier family 2, facilitated glucose transporter member 3 (465 Activities)

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SLC2A2 Tchem Solute carrier family 2, facilitated glucose transporter member 2 (428 Activities)

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SLC2A4 Tchem Solute carrier family 2, facilitated glucose transporter member 4 (396 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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NPC1 Tchem Niemann-Pick C1 protein (18985 Activities)

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RAB9A Tbio Ras-related protein Rab-9A (22488 Activities)

Discover Target: RAB9A

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

Discover Target: BAZ2B

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ITGAL Tclin Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 (760 Activities)

Discover Target: ITGAL

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Obiettivi associati (non umani)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

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Hdac6 Histone deacetylase 6 (222 Activities)

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Vibrio parahaemolyticus (473 Activities)

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CHO (4503 Activities)

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RAW264.7 (28094 Activities)

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Vero (26788 Activities)

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C6 (2371 Activities)

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H4 (48 Activities)

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BCHE Cholinesterase (8742 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Cirsium arvense (30 Activities)

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: Soluble in methanol (20 mg/ml), and 1:20 DMF:PBS(7.2) (~0.05 mg/ml).
• Sensibilità: Heat sensitive;Light sensitive;Moisture sensitive
• Punto di fusione (°C): 218-223°C
• Peso molecolare: 479.600 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 479.267 Da
• Monoisotopic Mass: 479.267 Da
• Topological Polar Surface Area: 95.900 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 859.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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