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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:50 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030753
Secondary Accession Numbers
  • HMDB30753
Metabolite Identification
Common NameAflatoxin Q1
DescriptionAflatoxin Q1 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. Aflatoxin Q1 is an extremely weak basic (essentially neutral) compound (based on its pKa). Metabolite of Aflatoxin B. It is a metabolite of Aflatoxin B. It can be found in Aspergillus flavus and Aspergillus parasiticus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). Aflatoxin Q1 is a mycotoxin.
Structure
Data?1563862032
SynonymsNot Available
Chemical FormulaC17H12O7
Average Molecular Weight328.273
Monoisotopic Molecular Weight328.058302738
IUPAC Name14-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 Name14-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 Number52819-96-2
SMILES
COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)CC1O)C(=O)O2
InChI Identifier
InChI=1S/C17H12O7/c1-21-9-5-10-11(6-2-3-22-17(6)23-10)15-14(9)12-7(18)4-8(19)13(12)16(20)24-15/h2-3,5-7,17-18H,4H2,1H3
InChI KeyGYNOTJLCULOEIM-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentDifurocoumarocyclopentenones
Alternative Parents
Substituents
  • Difurocoumarocyclopentenone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Dihydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Ketone
  • Acetal
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.11 g/LALOGPS
logP1.09ALOGPS
logP0.51ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)13.97ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area91.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability31.05 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]+175.07931661259
DarkChem[M-H]-174.00831661259
DeepCCS[M+H]+178.48830932474
DeepCCS[M-H]-176.1330932474
DeepCCS[M-2H]-209.93130932474
DeepCCS[M+Na]+185.23330932474
AllCCS[M+H]+173.632859911
AllCCS[M+H-H2O]+170.332859911
AllCCS[M+NH4]+176.732859911
AllCCS[M+Na]+177.632859911
AllCCS[M-H]-177.432859911
AllCCS[M+Na-2H]-176.532859911
AllCCS[M+HCOO]-175.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Aflatoxin Q1COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)CC1O)C(=O)O24473.1Standard polar33892256
Aflatoxin Q1COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)CC1O)C(=O)O23002.2Standard non polar33892256
Aflatoxin Q1COC1=CC2=C(C3C=COC3O2)C2=C1C1=C(C(=O)CC1O)C(=O)O22990.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aflatoxin Q1,1TMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1O[Si](C)(C)C)C(=O)O3)C1C=COC1O23041.9Semi standard non polar33892256
Aflatoxin Q1,1TBDMS,isomer #1COC1=CC2=C(C3=C1C1=C(C(=O)CC1O[Si](C)(C)C(C)(C)C)C(=O)O3)C1C=COC1O23272.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin Q1 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvt-0093000000-fe10fd0ad800536afceb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin Q1 GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-2009000000-bda75eab7bd63b12b8782017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aflatoxin Q1 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 Q1 10V, Positive-QTOFsplash10-03fr-0019000000-00df5dc80e17282b10f22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 20V, Positive-QTOFsplash10-01t9-0097000000-82241a07f8d6138202722015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 40V, Positive-QTOFsplash10-00pi-0190000000-5d9f73491dfaa85e4cbf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 10V, Negative-QTOFsplash10-004i-0039000000-32a84ed09d28ad1d064b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 20V, Negative-QTOFsplash10-056r-0069000000-03d8ded8829640e8be022015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 40V, Negative-QTOFsplash10-014i-2290000000-588badb61d5e55484c5b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 10V, Positive-QTOFsplash10-004i-0009000000-a6e8d4715f87e5602d4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 20V, Positive-QTOFsplash10-004i-0009000000-2a7fdd5bc031027a0b172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 40V, Positive-QTOFsplash10-0bti-0093000000-f8763e968a7c84feeeb32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 10V, Negative-QTOFsplash10-004i-0009000000-3c54e7c1cf524bc4e6012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 20V, Negative-QTOFsplash10-0a4i-0019000000-ada11d45d612eb31822e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aflatoxin Q1 40V, Negative-QTOFsplash10-01u0-0291000000-411daa9396c18e10c3e42021-09-22Wishart 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 IDFDB002685
KNApSAcK IDNot Available
Chemspider ID547126
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound630029
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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Aflatoxin Q1 → {11-methoxy-16,18-dioxo-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaen-14-yl}oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Aflatoxin Q1 → 3,4,5-trihydroxy-6-({11-methoxy-16,18-dioxo-6,8,19-trioxapentacyclo[10.7.0.0²,⁹.0³,⁷.0¹³,¹⁷]nonadeca-1(12),2(9),4,10,13(17)-pentaen-14-yl}oxy)oxane-2-carboxylic aciddetails