(2S)-2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-13C2)butanoyl]oxy}-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)(3,4-13C2)butanedioic acid

• ChemBase ID: 169499
• Molecular Formular: C34H59NO15
• Molecular Mass: 725.80057935
• Monoisotopic Mass: 725.40188955
• SMILES: C([C@H]([C@H]([C@@H](OC(=O)C[C@H]([13CH2][13C](=O)O)C(=O)O)C[C@H](C[C@H](O)CCCC[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](C[C@@H](CCCC[C@H](C[C@@H]([C@@H](N)C)O)O)O)C)OC(=O)C[C@H](C(=O)O)[13CH2][13C](=O)O)C
• InChI: 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/i14+1,15+1,28+1,29+1
• InChIKey: UVBUBMSSQKOIBE-OYKLVRFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-^1^3C₂)butanoyl]oxy}-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl]oxy}-2-oxoethyl)(3,4-^1^3C₂)butanedioic acid
• IUPAC Traditional name: (2S)-2-(2-{[(5R,6R,7S,9S,11R,16R,18S,19S)-19-amino-6-{[(3R)-3,4-dicarboxy(,4-^1^3C₂)butanoyl]oxy}-11,16,18-trihydroxy-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,4R,9R,11S,12S)-12-Amino-4,9,11-trihydroxy-2-methyltridecyl]-2-[(1R)-1-methylpentyl]-1,2-ethanediyl] Ester-13C4; Macrofusine-13C4; Fumonisin B1-13C4

Database IDs

• PubChem SID: 162263631
• PubChem CID: 71317006

CALCULATED PROPERTIES

• Acid pKa: 3.1587784
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -3.2378411
• LogD (pH = 7.4): -8.288933
• Log P: -0.66715026
• Molar Refractivity: 175.7057 cm^3
• Polarizability: 70.63428 Å^3
• Polar Surface Area: 288.51 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F862752

Labelled Fumonisin B1 (F862750). A mycotoxin produced by mold associated with corn. Fungal metabolite believed to cause leukoencephalomalacia in horses.

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)