(2S)-2-(2-{[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-13C2)butanoyl]oxy}-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)(3,4-13C2)butanedioic acid

• ChemBase ID: 169501
• Molecular Formular: C34H59NO14
• Molecular Mass: 709.80117935
• Monoisotopic Mass: 709.40697493
• SMILES: C([C@H]([C@H]([C@@H](OC(=O)C[C@H]([13CH2][13C](=O)O)C(=O)O)C[C@H](CCCCCC[C@@H](O)C[C@H](O)[C@@H](N)C)C)OC(=O)C[C@@H]([13CH2][13C](=O)O)C(=O)O)C)CCC
• Canonical SMILES: CCCC[C@H]([C@H]([C@@H](OC(=O)C[C@@H](C(=O)O)[13CH2][13C](=O)O)C[C@H](CCCCCC[C@H](C[C@@H]([C@@H](N)C)O)O)C)OC(=O)C[C@H](C(=O)O)[13CH2][13C](=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)/t20-,21+,22-,23-,24+,25+,26-,27-,32+/m0/s1/i15+1,16+1,28+1,29+1
• InChIKey: UXDPXZQHTDAXOZ-PUPATOSUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-{[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-^1^3C₂)butanoyl]oxy}-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)(3,4-^1^3C₂)butanedioic acid
• IUPAC Traditional name: (2S)-2-(2-{[(5R,6R,7S,9S,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-^1^3C₂)butanoyl]oxy}-16,18-dihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)(3,4-^1^3C₂)butanedioic acid
• Synonyms: (2R,2'R)-1,2,3-Propanetricarboxylic Acid 1,1'-[(1S,2R)-1-[(2S,9R,11S,12S)-12-Amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] Ester-13C4; Fumonisin B2-13C4

Database IDs

• PubChem SID: 162263633
• PubChem CID: 71317008

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

DETAILS

Toronto Research Chemicals - F862757

Labelled Fumonisin B2 (F862755). A mycotoxin produced by mold associated with corn. Inhibitor of sphingosine N-acyltransferase. Blocks the formation of ceramide from sphingosine.

REFERENCES

• Monbaliu, S., et al.: J. Agric. Food Chem., 58, 10475 (2010)
• Klosowski, G., et al.: Biores. Technol., 101, 9723 (2010)
• Soerensen, L., et al.: Anal. Bioanal. Chem., 398, 1535 (2010)