ContaminantDB: Fumonisin B1

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (16)XML

Record Information

Version

1.0

Creation Date

2009-11-12 23:15:30 UTC

Update Date

2026-03-25 19:28:00 UTC

Accession Number

CHEM002579

Identification

Common Name

Fumonisin B1

Class

Small Molecule

Description

Fumonisin B1 is from Fusarium moniliforme Fumonisin B1 is an inhibitor of ceramide synthase. Fumonisin B1 belongs to the family of Monoterpenes. These are compounds contaning a chain of two isoprene units.

Contaminant Sources

FooDB Chemicals
IARC Carcinogens Group 2B
T3DB toxins

Contaminant Type

Amine
Ester
Ether
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Fungal metabolite from fusarium monliforme	HMDB
Macrofusin	HMDB
Macrofusine	HMDB
Fumonisin-b1	MeSH, HMDB
Fumonisin b(1)	MeSH, HMDB
2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioate	Generator
Fumonisin b1	MeSH

Chemical Formula

C₃₄H₅₉NO₁₅

Average Molecular Mass

721.830 g/mol

Monoisotopic Mass

721.388 g/mol

CAS Registry Number

116355-83-0

IUPAC Name

2-[2-({19-amino-6-[(3,4-dicarboxybutanoyl)oxy]-11,16,18-trihydroxy-5,9-dimethylicosan-7-yl}oxy)-2-oxoethyl]butanedioic acid

Traditional Name

fumonisin B1

SMILES

CCCCC(C)C(OC(=O)CC(CC(O)=O)C(O)=O)C(CC(C)CC(O)CCCCC(O)CC(O)C(C)N)OC(=O)CC(CC(O)=O)C(O)=O

InChI Identifier

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)

InChI Key

UVBUBMSSQKOIBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as fumonisins. These are diesters of propane-1,2,3-tricarboxylic acid (TCA) and similar long-chain aminopolyol backbones (for FB1: 2S-amino-12S,16R-dimethyl-3S,5R,10R,14S,15R-pentahydroxyeicosane). Structurally, fumonisins resemble the sphingoid bases sphinganine (SA) and sphingosine (SO) to which TCA groups have been added at the C-14 and C-15 positions.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Fumonisins

Direct Parent

Fumonisins

Alternative Parents

Substituents

Fumonisin-skeleton
Fumonisin skeleton
Hexacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Amino acid
Polyol
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Primary amine
Amine
Organic oxide
Alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White to off-white powder

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-0.67	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	288.51 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	175.71 m³·mol⁻¹	ChemAxon
Polarizability	76.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9220052300-8bc211a1f0e18f5f642c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-0119021300-58bf8a40b1b65b070a7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0f89-0419000000-36226b94fa7eb1b4e8e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000900-f740c825dba70cda417a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-d3ac116c49813f029f07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0001000900-e4cb03af16b1f25db7ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-0119021300-9f43d64e017a08cd0da4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-0100029300-ffcf305584b8c580079e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-0100039000-bd98732f0b82eeec9ed5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0671-3230196000-96f4cea0ef59fce06f46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a6r-0100039300-2331d7d06cd8ddea069d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-3200059100-116d2ee3f8615476c28a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvl-8900461100-82cc98b5a91cfa3d76b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uki-0000115900-83b5f55ac961eb39a6f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-1310159500-7ce3a38d88b2e7e81ff1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9638261000-2d7017e2a28369e1bc77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-0100004900-353ce249b5b6219714ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0900048200-fb206e61aed4365064cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3900110000-bd100d6e48a5289e67f6	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

Fumonisins are similar in structure to the long-chain base backbones of sphingolipids, allowing it to inhibit of the biosynthesis of sphingosine and more complex sphingolipids by inhibiting the enzyme ceramide synthase. This causes the accumulation of sphinganine, sphingosine, and possibly also sphingosine 1-phosphate in cells and tissues, leading to apoptosis. Mycotoxins are often able to enter the liver and kidney by human organic anion transporters (hOATs) and human organic cation transporters (hOCTs). They can also inhibit uptake of anions and cations by these transporters, interefering with the secretion of endogenous metabolites, drugs, and xenobiotics including themselves. This results in increased cellular accumulation of toxic compounds causing nephro- and hepatotoxicity. (1, 7, 3, 4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (6)

Uses/Sources

Fumonisin B1 is the most prevalent member of a family of toxins, known as fumonisins, produced by several species of Fusarium molds, such as Fusarium moniliforme, which occur mainly in maize, wheat and other cereals. Fumonisin B1 contamination of maize has been reported worldwide at mg/kg levels. Human exposure occurs at levels of micrograms to milligrams per day and is greatest in regions where maize products are the dietary staple. (7)

Minimum Risk Level

Not Available

Health Effects

Fumonisin B1 is hepatotoxic and nephrotoxic, causing increased apoptosis followed by regenerative cell proliferation. Leukopenia, sepsis, bone marrow suppression, hemosiderosis, and multiple hemorrhages have all been reported. Contact with skin and eyes can cause coagulation necrosis. Angina, tachycardia, and hypotension may occur. Animals studies have also shown disturbed sphingolipid metabolism and cardiovascular dysfunction. (1, 7)

Symptoms

Anorexia, vomiting and diarrhea, which may be bloody, may occur. Shortness of breath, pulmonary hemorrhage, headache, and vertigo are other symptoms. (1)

Treatment

There are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Condiser activated charcoal if absorbed orally. Proceed with decontamination of the exposed region in case of eye or dermal contact. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. (1)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034702

FooDB ID

FDB013235

Phenol Explorer ID

Not Available

KNApSAcK ID