Fumonisin B2-13C34 - 10μg/mL in acetonitrile , CAS No.116355-84-1

CAS: 116355-84-1 Cat. No.: F299686 Molecular Weight: 705.83 EC Number: 601-424-4

GRADE & PURITY 10μg/mL in acetonitrile

Synonyms

1,2,3-Propanetricarboxylic acid, 1,1'-[1-(12-amino-9,11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1,2-ethanediyl] ester, [2S-[1[1R*(S*),2S*(S*),2(S*)],2R*,9S*,11R*,12R*]]-; Fumonisin B2 | LMSP01080023 | Q5508613 | (2R,2'R)-2,2'-((((5R,6R,7S,9S,16R,18

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

1, 2, 3-Propanetricarboxylic acid, 1, 1'-[1-(12-amino-9, 11-dihydroxy-2-methyltridecyl)-2-(1-methylpentyl)-1, 2-ethanediyl] ester, [2S-[1[1R*(S*), 2S*(S*), 2(S*)], 2R*, 9S*, 11R*, 12R*]]-; Fumonisin B2 | LMSP01080023 | Q5508613 | (2R, 2'R)-2, 2'-((((5R, 6R, 7S, 9S, 16R, 18

Specifications & Purity

10μg/mL in acetonitrile

Biochemical and Physiological Mechanisms

Cell proliferation inhibitor and apoptosis inducer. Mycotoxin, inhibits sphingolipid biosynthesis. Toxicological effects in vivo . Carcinogenic. Structural analog of Fumonisin B1. Active in vivo and in vitro .

Storage

Store at 2-8°C

Shipped In

Wet ice

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.

Names and Identifiers

• Canonical Smiles: CCCCC(C)C(C(CC(C)CCCCCCC(CC(C(C)N)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,16R,18S,19S)-19-amino-6-[(3R)-3,4-dicarboxybutanoyl]oxy-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy-2-oxoethyl]butanedioic acid
• InChIKey: UXDPXZQHTDAXOZ-STOIETHLSA-N
• INCHI: 1S/C34H59NO14/c1-5-6-12-21(3)32(49-31(43)18-24(34(46)47)16-29(40)41)27(48-30(42)17-23(33(44)45)15-28(38)39)14-20(2)11-9-7-8-10-13-25(36)19-26(37)22(4)35/h20-27,32,36-37H,5-19,35H2,1-4H3,(H,38,39)(H,40,41)(H,44,45)(H,46,47)/t20-,21+,22-,23+,24+,25+,26-,27-,32+/m0/s1
• Isomeric SMILES: CCCC[C@@H](C)[C@H]([C@H](C[C@@H](C)CCCCCC[C@H](C[C@@H]([C@H](C)N)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
• Molecular Weight: 705.83
• Reaxy-Rn: 7065823
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7065823&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 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 - Amino acid - Secondary alcohol - Carboxylic acid - Organic nitrogen compound - Organonitrogen compound - Primary aliphatic amine - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Amine - Alcohol - 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

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

Associated Targets(non-human)

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light Sensitive
• Molecular Weight: 705.800 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 31
• Exact Mass: 705.394 Da
• Monoisotopic Mass: 705.394 Da
• Topological Polar Surface Area: 268.000 Ų
• Heavy Atom Count: 49
• Formal Charge: 0
• Complexity: 1040.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 9
• 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

1. Ting Wang, Jie Cheng, Jinmao You, Zhiwei Sun.  (2023)  Highly selective and sensitive high performance liquid chromatography method for determination of fumonisins from feed samples with MIL-101 based dispersed micro-solid-phase extraction and precolumn fluorescence derivatization.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2023.109320]

2. Jiawei Zhang, Jie Zhao, Xinxin Shi, Zhiwei Sun, Jinmao You.  (2023)  Development of a method for the quantification of six mycotoxins in cereal samples using isotope-coded derivatization combined with ultra-high-performance liquid chromatography–tandem mass spectrometry.  JOURNAL OF FOOD COMPOSITION AND ANALYSIS,      [PMID:] [10.1016/j.jfca.2023.105347]

3. Zhengzong Wu, Enbo Xu, Muhammad F.J. Chughtai, Zhengyu Jin, Joseph Irudayaraj.  (2017)  Highly sensitive fluorescence sensing of zearalenone using a novel aptasensor based on upconverting nanoparticles.  FOOD CHEMISTRY,      [PMID:28407965] [10.1016/j.foodchem.2017.03.100]