Stereochemistry | ABSOLUTE |
Molecular Formula | C34H59NO15 |
Molecular Weight | 721.83 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC[C@@H](C)[C@@H](OC(=O)C[C@@H](CC(O)=O)C(O)=O)[C@H](C[C@@H](C)C[C@H](O)CCCC[C@@H](O)C[C@H](O)[C@H](C)N)OC(=O)C[C@@H](CC(O)=O)C(O)=O
InChI
InChIKey=UVBUBMSSQKOIBE-DSLOAKGESA-N
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
Molecular Formula | C34H59NO15 |
Molecular Weight | 721.83 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Fumonisin B, a mycotoxin produced by Fusarium moniliforme, causes neuronal degeneration, liver and renal toxicity, cancer, and another injury to animals. It was discovered, that fumonisin B1 inhibited sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis. It was suggested, that fumonisin B1 might have two modes of interaction with ceramide synthase. The “sphinganine-like” domain may interact with the sphinganine binding site, and the negatively charged tricarbyllic acid groups may interact with the fatty acyl-CoA binding site (by mimicking the polyanionic phosphate groups of the CoA). The latter interaction is probably not the most important because fumonisin B1 does not inhibit another CoA-dependent enzyme (serine palmitoyltransferase) or labeling of glycerolipids. The ability of fumonisin B1 to interact with both binding sites might account for its potency.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Patents
Sample Use Guides
Fumonisin B(1), causes equine leukoencephalomalacia and hepatotoxicity in BALB/c mice: mice were injected intraperitoneally with saline or 3 mg/kg of lipopolysaccharide (LPS) followed 2 h later by either a single or three daily subcutaneous doses of 2.25 mg/kg of FB(1).
Route of Administration:
Other
The stability of the cells to long-term incubations allowed to determine whether cells treated with fumonisin B1, followed by removal of the mycotoxin, recovered the ability to incorporate [14C]serine into sphingolipids. The experiment was conducted by incubating cultured cerebellar neurons with 25 uM fumonisin for the 48 or 96 h, and then removing the fumonisin B1 for the periods indicated and analyzing the incorporation of [14C] serine into sphingolipids during the last 24 h.