Aflatoxin M2

Basic Info

Common NameAflatoxin M2(F04924)
2D Structure
Description

Trace mycotoxin of Aspergillus flavus [CCD].Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, most notably Aspergillus flavus and Aspergillus parasiticus. Aflatoxins are toxic and among the most carcinogenic substances known. Aflatoxin M2 is a metabolite of aflatoxin B2 in milk of cattle fed on contaminated foods. (Wikipedia)

Aflatoxin M2 belongs to the family of Difurocoumarocyclopentenone Series. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton. Difurocoumarocyclopentenones are a subgroup of the aflatoxins and related compounds.

FRCD IDF04924
CAS Number6885-57-0
PubChem CID10903619
FormulaC17H14O7
IUPAC Name

None

InChI Key

OQLKWHFMUPJCJY-IAGOWNOFSA-N

InChI

InChI=1S/C17H14O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h6,16,20H,2-5H2,1H3/t16-,17-/m1/s1

Canonical SMILES

COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C(=C1)OC5C4(CCO5)O

Isomeric SMILES

COC1=C2C3=C(C(=O)CC3)C(=O)OC2=C4C(=C1)O[C@@H]5[C@]4(CCO5)O

WikipediaAflatoxin M2
Synonyms
        
            (3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0;{2,9}.0;{3,7}.0;{13,17}]nonadeca-1,9,11,13(17)-tetraene-16,18-dione
        
            AFLATOXIN M2
        
            UNII-U3L0HCE5OI
        
            U3L0HCE5OI
        
            4-Hydroxyaflatoxin B2
        
            EINECS 229-989-9
        
            BRN 1440986
        
            ZINC402709
        
            ZB012915
Classifies
                

                  
                    Fungal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
SubclassFuranocoumarins
Intermediate Tree NodesAngular furanocoumarins - Aflatoxins
Direct ParentDifurocoumarocyclopentenones
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsDifurocoumarocyclopentenone - Difurocoumarin - Benzopyran - 1-benzopyran - Coumaran - Anisole - Aryl ketone - Aryl alkyl ketone - Alkyl aryl ether - Pyranone - Benzenoid - Pyran - Heteroaromatic compound - Tetrahydrofuran - Tertiary alcohol - Ketone - Lactone - Oxacycle - Ether - Acetal - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Organooxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton.

Properties

Property NameProperty Value
Molecular Weight330.292
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count1
Complexity655
Monoisotopic Mass330.074
Exact Mass330.074
XLogP0.2
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8186
Human Intestinal AbsorptionHIA+0.8727
Caco-2 PermeabilityCaco2-0.6429
P-glycoprotein SubstrateSubstrate0.6999
P-glycoprotein InhibitorNon-inhibitor0.6033
Non-inhibitor0.8275
Renal Organic Cation TransporterNon-inhibitor0.7856
Distribution
Subcellular localizationMitochondria0.8279
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7622
CYP450 2D6 SubstrateNon-substrate0.8286
CYP450 3A4 SubstrateSubstrate0.5497
CYP450 1A2 InhibitorNon-inhibitor0.6712
CYP450 2C9 InhibitorNon-inhibitor0.6508
CYP450 2D6 InhibitorNon-inhibitor0.8136
CYP450 2C19 InhibitorNon-inhibitor0.6779
CYP450 3A4 InhibitorNon-inhibitor0.8544
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9205
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9811
Non-inhibitor0.8858
AMES ToxicityAMES toxic0.5108
CarcinogensNon-carcinogens0.9702
Fish ToxicityHigh FHMT0.6026
Tetrahymena Pyriformis ToxicityHigh TPT0.9957
Honey Bee ToxicityHigh HBT0.6750
BiodegradationNot ready biodegradable0.6436
Acute Oral ToxicityIII0.3942
Carcinogenicity (Three-class)Danger0.3891
Model Value Unit
Absorption
Aqueous solubility-2.7806LogS
Caco-2 Permeability0.6860LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.0117LD50, mol/kg
Fish Toxicity0.6880pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9065pIGC50, ug/L

References

TitleJournalDatePubmed ID
Assessment of Aflatoxin M1 and M2 exposure risk through Oaxaca cheese consumption in southeastern Mexico.Int J Environ Health Res2018 Apr29560730
A simple sample pretreatment method for multi-mycotoxin determination in eggs by liquid chromatography tandem mass spectrometry.J Chromatogr A2015 Oct 2326385084
Rapid determination of total aflatoxins and ochratoxins A in meat products by immuno-affinity fluorimetry.Food Chem2015 Jul 1525722162
Determination of aflatoxin M1 in breast milk as a biomarker of maternal and infant exposure in Colombia.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525959253
Flow-based impedimetric immunosensor for aflatoxin analysis in milk products.Appl Biochem Biotechnol2014 Oct24867630
Modulation of macrophage activity by aflatoxins B1 and B2 and their metabolites aflatoxins M1 and M2.Toxicon2012 May22402176
[Using HTS-ELISA method to make anti-aflatoxin M1 monoclonal antibody].Wei Sheng Wu Xue Bao2010 Oct21141478
Occurrence of aflatoxins M(1) and M(2) in milk commercialized in Ribeirão Preto-SP, Brazil.Food Addit Contam2003 Jan12519721
Comparison of nixtamalization and extrusion processes for a reduction in aflatoxin content.Food Addit Contam2002 Sep12396399
Variations in the levels of aflatoxin in cows milk consumed in the city of São Paulo, Brazil.Food Addit Contam1989 Jul-Sep2498138
An epidemiological investigation associating aflatoxin M1 with milk production in dairy cattle.Vet Hum Toxicol1988 Feb3127990
Rapid liquid chromatographic determination of aflatoxins M1 and M2 in artificially contaminated fluid milks: collaborative study.J Assoc Off Anal Chem1986 Sep-Oct3095309
Improved cleanup for liquid chromatographic analysis and fluorescence detection of aflatoxins M1 and M2 in fluid milk products.J Assoc Off Anal Chem1984 Nov-Dec6440891
Reverse phase liquid chromatographic determination and confirmation of aflatoxin M1 in cheese.J Assoc Off Anal Chem1984 May-Jun6430865
Aflatoxins in human breast milk.Ann Trop Paediatr1984 Jun6083747
The role of zinc in the aflatoxigenic potential of Aspergillus flavus NRRL 3251 on foodstuffs.Mycopathologia1981 Apr 106787428

Targets

Target Details

Cytochrome P450 2C9

General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]
Target Details

Cytochrome P450 3A4

General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Girennavar B, Jayaprakasha GK, Patil BS: Potent inhibition of human cytochrome P450 3A4, 2D6, and 2C9 isoenzymes by grapefruit juice and its furocoumarins. J Food Sci. 2007 Oct;72(8):C417-21. [17995595 ]