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

• ChemBase ID: 106060
• Molecular Formular: C34H65NO17
• Molecular Mass: 759.8764
• Monoisotopic Mass: 759.42524963
• SMILES: O.O.O.CCCCC(C)C(OC(=O)CC(CC(=O)O)C(=O)O)C(CC(C)CCCCCCC(O)CC(O)C(C)N)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.O.O.O
• InChI: InChI=1S/C34H59NO14.3H2O/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);3*1H2
• InChIKey: SQOLDRLMQMFCAL-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 trihydrate
• IUPAC Traditional name: 2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-16,18-dihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid trihydrate
• Synonyms: FUMONISIN B₂

Database IDs

• CAS Number: 116355-84-1
• PubChem SID: 162094223
• PubChem CID: 44134725

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

MP Biomedicals - 02198781

From Fusarium moniliforme
White powder.
Fungal metabolite
Inhibits sphingolipid biosynthesis.

REFERENCES

• E.Wang et al., J. Biol. Chem., 266: 1486, (1991).