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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:03 UTC
Update Date2022-03-07 02:52:34 UTC
HMDB IDHMDB0030479
Secondary Accession Numbers
  • HMDB30479
Metabolite Identification
Common NameAflatoxin M1
DescriptionAflatoxin G belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone ring fused to the coumarin moiety of the difurocoumarin skeleton. Aflatoxin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Aflatoxin G is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. A broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin G belongs to the family of Difurocoumarolactone Series.
Structure
Data?1563861991
Synonyms
ValueSource
Aflatoxin g1HMDB
4-Hydroxyaflatoxin b1ChEBI
AFM1ChEBI
4 Hydroxyaflatoxin b1MeSH
Aflatoxin m1, cis(+-)-isomerMeSH
Aflatoxin mMeSH
Chemical FormulaC17H12O7
Average Molecular Weight328.273
Monoisotopic Molecular Weight328.058302738
IUPAC Name(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione
Traditional Name(3R,7R)-3-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaene-16,18-dione
CAS Registry Number6795-23-9
SMILES
[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O
InChI Identifier
InChI=1S/C17H12O7/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/h4-6,16,20H,2-3H2,1H3/t16-,17-/m1/s1
InChI KeyMJBWDEQAUQTVKK-IAGOWNOFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as difurocoumarolactones. These are polycyclic aromatic compounds containing a delta-valerolactone ring fused to the coumarin moiety of the difurocoumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentDifurocoumarolactones
Alternative Parents
Substituents
  • Difurocoumarolactone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Dihydrofuran
  • Carboxylic acid ester
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point299 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.99 g/LALOGPS
logP1.21ALOGPS
logP0.93ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)11.42ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area91.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.67 m³·mol⁻¹ChemAxon
Polarizability31.07 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.17531661259
DarkChem[M-H]-171.82731661259
DeepCCS[M-2H]-202.84330932474
DeepCCS[M+Na]+177.69330932474
AllCCS[M+H]+173.332859911
AllCCS[M+H-H2O]+169.932859911
AllCCS[M+NH4]+176.432859911
AllCCS[M+Na]+177.232859911
AllCCS[M-H]-177.532859911
AllCCS[M+Na-2H]-176.732859911
AllCCS[M+HCOO]-175.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Aflatoxin M1[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O4181.7Standard polar33892256
Aflatoxin M1[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O2816.1Standard non polar33892256
Aflatoxin M1[H][C@]12OC=C[C@@]1(O)C1=C(O2)C=C(OC)C2=C1OC(=O)C1=C2CCC1=O2992.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aflatoxin M1,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@]1(O[Si](C)(C)C)C=CO[C@@H]1O22959.0Semi standard non polar33892256
Aflatoxin M1,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1)C(=O)O3)[C@]1(O[Si](C)(C)C(C)(C)C)C=CO[C@@H]1O23169.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin M1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1093000000-d4b028c14eb0b56a6dab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin M1 GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-3019000000-16e7ca1f490d12f2251c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin M1 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Positive-QTOFsplash10-004i-0019000000-bbac981b86ec0492f21d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Positive-QTOFsplash10-01t9-0049000000-6f31a5efa1e5ce49dc2e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Positive-QTOFsplash10-03fs-4590000000-05fb74b57fa5ff2e34e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Negative-QTOFsplash10-004i-0029000000-391e040bf68fd12a6ee32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Negative-QTOFsplash10-004i-0029000000-8af815da6e7ffdd1aa662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Negative-QTOFsplash10-01td-4490000000-718acd1824f6a41573d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Negative-QTOFsplash10-004i-0009000000-3eb691afb29ed57b3f5f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Negative-QTOFsplash10-004i-0019000000-378c0fff332dffa4ac832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Negative-QTOFsplash10-004j-1393000000-72a0612864b183b854402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 10V, Positive-QTOFsplash10-004i-0009000000-a6e8d4715f87e5602d4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 20V, Positive-QTOFsplash10-004i-0009000000-60957124411bf6b339802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin M1 40V, Positive-QTOFsplash10-0fbi-0079000000-fe971dd41bcdbd5a26bd2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002343
KNApSAcK IDC00023618
Chemspider ID13775
KEGG Compound IDC16755
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14421
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .