Dihydrocytochalasin B - ≥98%(HPLC) , CAS No.39156-67-7

CAS: 39156-67-7 Cat. No.: D139525 Molecular Weight: 481.62 EC Number: 254-324-4

GRADE & PURITY ≥98%(HPLC)

Synonyms

MFCD12910542 | EINECS 254-324-4 | 21,22-Dihydrocytochalasan B | 7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E)-diene-1,23-dione | Cytochalasin H2B | dihydrocytochalasin B | 21,22-Dihydrophomin | 24-OXA(14)CYTOCHALASA-6(12),1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Dihydrocytochalasin B induces changes in cell morphology and motility with no effect on sugar transport. Dihydrocytochalasin B is used as specific marker in studies of high affinity cytochalasin binding sites unrelated to sugar transport. Dihydrocytochalasin B also disrupts the equilibrium between monomeric and polymeric actin.
Marker for high affinity cytochalasin B binding sites. Cytochalasins are used as tools in cytological research, and in in the field of actin polymerisation

Specifications

Synonyms

MFCD12910542 | EINECS 254-324-4 | 21, 22-Dihydrocytochalasan B | 7(S), 20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12), 13(E)-diene-1, 23-dione | Cytochalasin H2B | dihydrocytochalasin B | 21, 22-Dihydrophomin | 24-OXA(14)CYTOCHALASA-6(12), 1

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Effect on cell motility and morphology similar to that of cytochalasin B; does not inhibit glucose transport.Cytokinesis inhibitor and induces changes in cell morphology and motility. Disrupts actin structure and inhibits ability of serum growth factors t

Storage

Store at -20°C

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%(HPLC)

Names and Identifiers

• Canonical Smiles: CC1CCCC(CCC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
• IUPAC Name: (1S,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]henicos-12-ene-3,21-dione
• InChIKey: WIULKAASLBZREV-RXPQEOCGSA-N
• INCHI: 1S/C29H39NO5/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/h4-6,8,11-12,14,18-19,22-24,26-27,31,33H,3,7,9-10,13,15-17H2,1-2H3,(H,30,34)/b14-8+/t18-,19-,22-,23+,24+,26+,27-,29-/m1/s1
• Isomeric SMILES: C[C@@H]1CCC[C@H](CCC(=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 Germany: 3
• Molecular Weight: 481.62
• Reaxy-Rn: 37623011
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=37623011&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cytochalasans
• Subclass: Cytochalasins
• Intermediate Tree Nodes: Not available
• Direct Parent: Cytochalasins
• Alternative Parents: Isoindolones Isoindoles Benzene and substituted derivatives Pyrrolidine-2-ones Secondary carboxylic acid amides Carboxylic acid esters Cyclic alcohols and derivatives Secondary alcohols Lactams Lactones Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Lactone cytochalasin skeleton - Cytochalasin - Isoindolone - Isoindoline - Isoindole - Isoindole or derivatives - Monocyclic benzene moiety - Pyrrolidone - 2-pyrrolidone - Benzenoid - Pyrrolidine - Cyclic alcohol - Secondary alcohol - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Oxacycle - Monocarboxylic acid or derivatives - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Aromatic heteropolycyclic compound
• Description: 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: 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Acetone, DMSO, 100% Ethanol, Methanol
• Sensitivity: Light Sensitive
• Melt Point(°C): 204°C
• Molecular Weight: 481.600 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 481.283 Da
• Monoisotopic Mass: 481.283 Da
• Topological Polar Surface Area: 95.900 Ų
• Heavy Atom Count: 35
• Formal Charge: 0
• Complexity: 818.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1