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Details

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
Structure of FUMONISIN B1

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

HIDE SMILES / InChI

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

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
3ZZM97XZ32
Record Status Validated (UNII)
Record Version