Fumonisin B1 - ≥98%(HPLC) , CAS No.116355-83-0

CAS: 116355-83-0 Cat. No.: F135527 Molecular Weight: 721.83 EC Number: 621-436-3

GRADE & PURITY ≥98%(HPLC)

Synonyms

HSDB 7077 | EX-A8017 | Fumonisin B1 50 microg/mL in Acetonitrile/Water | fumonisin-B1 | SCHEMBL13555629 | fumonisin b1 | fumonisin B(1) | UNII-3ZZM97XZ32 | AKOS024457430 | FUMONISIN B1 [IARC] | DTXSID6020644 | HY-N6719 | 1,2,3-PROPANETRICARBOXYLIC ACID, 1

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Fumonisin B1 is a fungal metabolite produced by Fusarium moniliforme, that has been shown to inhibit protein serine/threonine phosphatases (PP1, PP2A, PP2B, PP2C, and PP5/T/K/H), and is most effective with PP5. It has been shown to stimulate the activation of mitogen-activated protein kinase. Fumonisin B1 has been observed to inhibit sphingolipid biosynthesis, preferentially inhibiting sphingomyelin biosynthesis versus glycosphingolipids in neuronal cells. In primary rat liver cells, fumonisin B1 blocked biosynthesis of de novo sphingolipids through LASS (ceramide synthase) inhibition. Caspase-3 activated or DNA fragmented apoptosis induced by fumonisin B1 binding to a TNF receptor has been documented in many human and rat cell lines. Fumonisin B1 has displayed immunotoxic effects by increasing expression of IL-1β, TNFα, IFN-γ; (interferon γ), IL-1α, IL-6, IL-10, IL-18 and IL-12 in varying mouse cells. Immunotoxicity of fumonisin B1 in human dendritic cells has been demonstrated through expression of chemokine CXCL9 and IFN-γ. Further, fumonisin B1 is an activator of Akt.
A serine/threonine phosphatase inhibitor.

Specifications

Synonyms

HSDB 7077 | EX-A8017 | Fumonisin B1 50 microg/mL in Acetonitrile/Water | fumonisin-B1 | SCHEMBL13555629 | fumonisin b1 | fumonisin B(1) | UNII-3ZZM97XZ32 | AKOS024457430 | FUMONISIN B1 [IARC] | DTXSID6020644 | HY-N6719 | 1, 2, 3-PROPANETRICARBOXYLIC ACID, 1

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Fungal metabolite believed to cause leukoencephalomalacia in horses.Mycotoxin and protein serine/threonine phosphatase inhibitor (IC 50 values are 80 μM (PP5), 0.3 (PP2Cα), 0.4 ( PP2A), 0.5 (PP1γ2) and 3 mM (PP2B)). Cell proliferation inhibitor and apopto

Storage

Store at -20°C, Argon charged

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: CCCCC(C)C(C(CC(C)CC(CCCCC(CC(C(C)N)O)O)O)OC(=O)CC(CC(=O)O)C(=O)O)OC(=O)CC(CC(=O)O)C(=O)O
• IUPAC Name: (2R)-2-[2-[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• InChIKey: UVBUBMSSQKOIBE-DSLOAKGESA-N
• INCHI: 1S/C34H59NO15/c1-5-6-9-20(3)32(50-31(44)17-23(34(47)48)15-29(41)42)27(49-30(43)16-22(33(45)46)14-28(39)40)13-19(2)12-24(36)10-7-8-11-25(37)18-26(38)21(4)35/h19-27,32,36-38H,5-18,35H2,1-4H3,(H,39,40)(H,41,42)(H,45,46)(H,47,48)/t19-,20+,21-,22+,23+,24+,25+,26-,27-,32+/m0/s1
• Isomeric SMILES: CCCC[C@@H](C)[C@H]([C@H](C[C@@H](C)C[C@@H](CCCC[C@H](C[C@@H]([C@H](C)N)O)O)O)OC(=O)C[C@@H](CC(=O)O)C(=O)O)OC(=O)C[C@@H](CC(=O)O)C(=O)O
• WGK Germany: 3
• RTECS: TZ8350000
• UN Number: 2811
• Packing Group: III
• Molecular Weight: 721.83
• Reaxy-Rn: 7071407
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7071407&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Fumonisins

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Fumonisins
• Intermediate Tree Nodes: Not available
• Direct Parent: Fumonisins
• Alternative Parents: Hexacarboxylic acids and derivatives Fatty acid esters Secondary alcohols Carboxylic acid esters Amino acids 1,2-aminoalcohols Polyols Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fumonisin-skeleton - Fumonisin skeleton - Hexacarboxylic acid or derivatives - Fatty acid ester - Fatty acyl - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Secondary alcohol - Amino acid - Polyol - Carboxylic acid - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Primary amine - Amine - Organic oxide - Alcohol - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions.
• External Descriptors: Sphingoid base analogs

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

Chemical and Physical Properties

• Solubility: Soluble in water (25 mg/mL), methanol (10 mg/mL), acetonitrile, and DMSO (10 mM).
• Sensitivity: Moisture & Light sensitive
• Molecular Weight: 721.800 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 31
• Exact Mass: 721.388 Da
• Monoisotopic Mass: 721.388 Da
• Topological Polar Surface Area: 289.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 1070.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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