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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:23:24 UTC
Update Date2021-10-01 22:35:35 UTC
HMDB IDHMDB0254198
Secondary Accession NumbersNone
Metabolite Identification
Common NameLumazine
DescriptionLumazine belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. Lumazine has been detected, but not quantified in, soy beans (Glycine max). This could make lumazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Lumazine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lumazine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lumazine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1H,3H-Pteridine-2,4-dioneChEBI
2,4(3H,8H)-PteridinedioneChEBI
2,4-DihydroxypteridineChEBI
Pteridine-2,4-dioneChEBI
2,4-PteridinedioneMeSH
Chemical FormulaC6H4N4O2
Average Molecular Weight164.1216
Monoisotopic Molecular Weight164.033425392
IUPAC Name2,3,4,8-tetrahydropteridine-2,4-dione
Traditional Name2,4(3H,8H)-pteridinedione
CAS Registry NumberNot Available
SMILES
O=C1NC(=O)C2=NC=CNC2=N1
InChI Identifier
InChI=1S/C6H4N4O2/c11-5-3-4(8-2-1-7-3)9-6(12)10-5/h1-2H,(H2,8,9,10,11,12)
InChI KeyUYEUUXMDVNYCAM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassNot Available
Direct ParentPteridines and derivatives
Alternative Parents
Substituents
  • Pteridine
  • Pyrimidone
  • Pyrazine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Urea
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-1.5ALOGPS
logP-0.83ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)6.96ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity37.89 m³·mol⁻¹ChemAxon
Polarizability13.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+131.60730932474
DeepCCS[M-H]-127.77930932474
DeepCCS[M-2H]-165.28330932474
DeepCCS[M+Na]+140.82230932474
AllCCS[M+H]+135.532859911
AllCCS[M+H-H2O]+130.932859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+141.032859911
AllCCS[M-H]-129.932859911
AllCCS[M+Na-2H]-130.532859911
AllCCS[M+HCOO]-131.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LumazineO=C1NC(=O)C2=NC=CNC2=N12435.7Standard polar33892256
LumazineO=C1NC(=O)C2=NC=CNC2=N11598.2Standard non polar33892256
LumazineO=C1NC(=O)C2=NC=CNC2=N12023.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lumazine,1TMS,isomer #1C[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O1875.8Semi standard non polar33892256
Lumazine,1TMS,isomer #1C[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O1934.0Standard non polar33892256
Lumazine,1TMS,isomer #1C[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O2962.1Standard polar33892256
Lumazine,1TMS,isomer #2C[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O1895.1Semi standard non polar33892256
Lumazine,1TMS,isomer #2C[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O1985.1Standard non polar33892256
Lumazine,1TMS,isomer #2C[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O2921.9Standard polar33892256
Lumazine,2TMS,isomer #1C[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C)C2=O1911.0Semi standard non polar33892256
Lumazine,2TMS,isomer #1C[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C)C2=O2073.7Standard non polar33892256
Lumazine,2TMS,isomer #1C[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C)C2=O2571.1Standard polar33892256
Lumazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O2050.4Semi standard non polar33892256
Lumazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O2111.3Standard non polar33892256
Lumazine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)N=C2[NH]C=CN=C2C1=O3010.3Standard polar33892256
Lumazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O2117.8Semi standard non polar33892256
Lumazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O2231.1Standard non polar33892256
Lumazine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)[NH]C2=O2983.9Standard polar33892256
Lumazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2336.7Semi standard non polar33892256
Lumazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2480.0Standard non polar33892256
Lumazine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CN=C2C1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2666.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lumazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-3900000000-3617b8c9e39f70fdaeb82021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 40V, Positive-QTOFsplash10-014l-9000000000-16eaed24ab2844ae48b12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 35V, Positive-QTOFsplash10-00dl-5900000000-30dd9ba75566128dcec02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 10V, Positive-QTOFsplash10-014i-0900000000-1fafe746e317cff4f5fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 20V, Positive-QTOFsplash10-00dl-7900000000-257abbdc532dc04506372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 35V, Negative-QTOFsplash10-001i-9200000000-1affa7fcb423cd9f39d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 35V, Negative-QTOFsplash10-01vo-5900000000-8507d657c7932fa499ca2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lumazine 35V, Negative-QTOFsplash10-03di-0900000000-b0fc15cf3b6524adc1da2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 10V, Positive-QTOFsplash10-014i-0900000000-1f8a6f89c469bccc4a812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 20V, Positive-QTOFsplash10-01b9-0900000000-703155048c9bcdf9564c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 40V, Positive-QTOFsplash10-01b9-9400000000-c2ec60b285fa03ba74302016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 10V, Negative-QTOFsplash10-03di-0900000000-0bf87084a2f5f3fa468e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 20V, Negative-QTOFsplash10-0006-9400000000-cb5a8c18cc8e8f5707012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 40V, Negative-QTOFsplash10-0006-9100000000-108d5a56501ec61db1342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 10V, Positive-QTOFsplash10-014i-0900000000-7fce5dedcd041913d9792021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 20V, Positive-QTOFsplash10-014i-0900000000-040e77259a409a49cc602021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 40V, Positive-QTOFsplash10-014i-9200000000-2be94aad3be1591122392021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 10V, Negative-QTOFsplash10-03di-0900000000-c571fb939b2bb15221252021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 20V, Negative-QTOFsplash10-03dl-7900000000-442377bf30dc3825297f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumazine 40V, Negative-QTOFsplash10-0006-9000000000-0e6d54edacd59d4f2cce2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005597
KNApSAcK IDC00019640
Chemspider ID9832
KEGG Compound IDC03212
BioCyc IDCPD-15309
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16489
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Enzymes

General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
A6L3K7
Molecular weight:
18127.525
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
A7ZBS6
Molecular weight:
16719.365
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
A6L8H3
Molecular weight:
17486.735
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate (PubMed:10482294, PubMed:16165152, PubMed:20195542). This is the penultimate step in the biosynthesis of riboflavin. The isozyme RibH2 but not RibH1 is essential for Brucella intracellular survival and replication inside macrophages or in mice (PubMed:20195542). Displays low catalytic activity in comparison with the isozyme RibH1 (PubMed:16165152). Is a highly immunogenic protein (PubMed:14500496). Activates dendritic cells (DCs) in vitro, increasing the levels of costimulatory molecules and the secretion of proinflammatory cytokines, and recruits DCs, B cells and CD8+ T cells in vivo, both effects in a TLR4-dependent manner (PubMed:16455994). Induces the cross presentation of covalently attached peptides and generates a strong and long-lasting humoral immune response without adjuvants; TLR4 signaling is necessary for the induction of the cytotoxic response but not for antigen cross presentation (PubMed:23029192). Elicits a TLR4-mediated protective response against B16 melanoma in mice, slowing tumor growth and prolonging mice survival (PubMed:25973756).
Gene Name:
RIBH2
Uniprot ID:
Q2YKV1
Molecular weight:
17355.785
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
B9KFN9
Molecular weight:
16643.205
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
C4Z8N0
Molecular weight:
16569.105
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
Q8E0I2
Molecular weight:
17186.645
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
Q9REF4
Molecular weight:
16952.53
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
Q5PFS8
Molecular weight:
16008.135
General function:
Not Available
Specific function:
Catalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Gene Name:
RIBH
Uniprot ID:
B9E7J1
Molecular weight:
16541.855

Only showing the first 10 proteins. There are 23 proteins in total.