Fumonisin B2 - ≥98%(HPLC) , CAS No.116355-84-1

CAS: 116355-84-1 Cat. No.: F139526 Formula: C₃₄H₅₉NO₁₄ Molecular Weight: 705.83 EC Number: 601-424-4

GRADE & PURITY ≥98%(HPLC)

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

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Structural analog of Fumonisin B1. Fumonisin B2 is more cytotoxic than Fumonisin B1. Fumonisin B2 inhibits sphingosine acyl-transterase.
Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine

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

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine.

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

Pubchem Sid

504761008

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504761008

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

• Solubility: Soluble in water (25 mg/ml), and methanol (10 mg/ml).
• Sensitivity: Light Sensitive；Moisture 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