2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-16,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid

• ChemBase ID: 133459
• Molecular Formular: C34H59NO14
• Molecular Mass: 705.83056
• Monoisotopic Mass: 705.39355557
• 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
• Canonical SMILES: CCCCC(C(C(OC(=O)CC(C(=O)O)CC(=O)O)CC(CCCCCCC(CC(C(N)C)O)O)C)OC(=O)CC(C(=O)O)CC(=O)O)C
• InChI: 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)
• InChIKey: UXDPXZQHTDAXOZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-16,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid
• IUPAC Traditional name: fumonisin B2
• Synonyms: Fumonisin B2 from Fusarium moniliforme

Database IDs

• CAS Number: 116355-84-1
• MDL Number: MFCD00133350
• PubChem SID: 162227736; 24894857
• PubChem CID: 3432

CALCULATED PROPERTIES

• Acid pKa: 3.1587622
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -1.8511224
• LogD (pH = 7.4): -6.9022145
• Log P: 0.7195988
• Molar Refractivity: 174.0362 cm^3
• Polarizability: 69.95746 Å^3
• Polar Surface Area: 268.28 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: TZ8335000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-36/37/38-40
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H330-H335-H351
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - F3771

Biochem/physiol Actions
Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine.
General description
Mycotoxin originally isolated from Fusarium sp, which grows on corn. Produces neural tube defects and craniofacial abnormalities in fetuses.1 Many strains of Aspergillus niger growing naturally on grapes are capable of producing fumonisin B2,2 so it is now a concern for human consumption of grapes, raisins, and wine.