LUMAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H4N4O2
Molecular Weight	164.1216
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NC(=O)C2=C(N1)N=CC=N2

InChI

InChIKey=UYEUUXMDVNYCAM-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C6H4N4O2
Molecular Weight	164.1216
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Effect of substituents of alloxazine derivatives on the selectivity and affinity for adenine in AP-site-containing DNA duplexes.	2010-11-07	20820650
Oxidation of 2'-deoxyadenosine 5'-monophosphate photoinduced by lumazine.	2010-10-21	20873833
Bioinformatics analysis of Brucella vaccines and vaccine targets using VIOLIN.	2010-09-27	20875156
Structural study and thermodynamic characterization of inhibitor binding to lumazine synthase from Bacillus anthracis.	2010-09	20823551
1H-pteridine-2,4-dione (lumazine): a new MALDI matrix for complex (phospho)lipid mixtures analysis.	2010-09	20593166
Penilumamide, a novel lumazine peptide isolated from the marine-derived fungus, Penicillium sp. CNL-338.	2010-05-07	20401392
An atypical riboflavin pathway is essential for Brucella abortus virulence.	2010-02-25	20195542
(6-Acetyl-1,3,7-trimethyl-lumazine-κO,N,O)bis-(triphenyl-phosphine-κP)copper(I) hexa-fluorido-phosphate.	2010-01-13	21579625
Synthesis and in vitro evaluation of pteridine analogues as monoamine oxidase B and nitric oxide synthase inhibitors.	2009-11-01	19804982
The photosensitizing activity of lumazine using 2'-deoxyguanosine 5'-monophosphate and HeLa cells as targets.	2009-11	19862412
Discovery and development of a small molecule library with lumazine synthase inhibitory activity.	2009-08-07	19552377
Substrate Orientation and Catalysis at the Molybdenum Site in Xanthine Oxidase: CRYSTAL STRUCTURES IN COMPLEX WITH XANTHINE AND LUMAZINE.	2009-03-27	19109252
Structure of lumazine protein, an optical transponder of luminescent bacteria.	2008-09-26	18602927
Luminescent sensor for Cd2+, Hg2+ and Ag+ in water based on a sulphur-containing receptor: quantitative binding-softness relationship.	2008-09-10	18780324
Redox behavior of anticancer chalcone on a glassy carbon electrode and evaluation of its interaction parameters with DNA.	2008-08	19325813
Metal complexes with the ligand derived from 6-acetyl-1,3,7-trimethyllumazine and benzohydrazide. Molecular structures of two new Co(II) and Rh(III) complexes and analysis of in vitro antitumor activity.	2008-08	18538411
Role of extracellular superoxide in neutrophil activation: interactions between xanthine oxidase and TLR4 induce proinflammatory cytokine production.	2008-04	18287332
High-performance liquid chromatographic determination of glyoxal and methylglyoxal in urine by prederivatization to lumazinic rings using in serial fast scan fluorimetric and diode array detectors.	2007-12-01	17884007
Lumazine proteins from photobacteria: localization of the single ligand binding site to the N-terminal domain.	2007-12	18020947
Structural characterization of new Cd(2+) fluorescent sensor based on lumazine ligand: AM1 and ab initio studies.	2007-11	17395527
Increases in microbial nitrogen production and efficiency in vitro with three inhibitors of ruminal methanogenesis.	2007-04	17612604
Correcting ligands, metabolites, and pathways.	2006-11-28	17132165
Multiple assembly states of lumazine synthase: a model relating catalytic function and molecular assembly.	2006-09-29	16935304
Random isotopolog libraries for protein perturbation studies. 13C NMR studies on lumazine protein of Photobacterium leiognathi.	2005-11-25	16292826
Design, synthesis, and biochemical evaluation of 1,5,6,7-tetrahydro-6,7-dioxo-9-D-ribitylaminolumazines bearing alkyl phosphate substituents as inhibitors of lumazine synthase and riboflavin synthase.	2005-09-30	16277343
Biosynthesis of flavocoenzymes.	2005-06	16010344
1,3-Dimethyllumazine derivatives from Limnatis nilotica.	2005-06	15974624
Genome-scale reconstruction of the metabolic network in Staphylococcus aureus N315: an initial draft to the two-dimensional annotation.	2005-03-07	15752426
Structural basis of charge transfer complex formation by riboflavin bound to 6,7-dimethyl-8-ribityllumazine synthase.	2004-08	15265040
Human infection with M- strain of Brucella canis.	2004-01	15078613
Effects of several inhibitors on pure cultures of ruminal methanogens.	2004	15281932
Riboflavin synthase of Schizosaccharomyces pombe. Protein dynamics revealed by 19F NMR protein perturbation experiments.	2003-12-23	14690539
Molecular probe for selective detection of thiols in water of neutral pH.	2003-08-04	12852962
A structure-based model of the reaction catalyzed by lumazine synthase from Aquifex aeolicus.	2003-04-18	12684006
Use of a pharmacophore model to discover a new class of influenza endonuclease inhibitors.	2003-03-27	12646026
Incorporation of an amide into 5-phosphonoalkyl-6-D-ribitylaminopyrimidinedione lumazine synthase inhibitors results in an unexpected reversal of selectivity for riboflavin synthase vs lumazine synthase.	2002-10-04	12353976
Design, synthesis, and evaluation of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase.	2002-08-09	12153285
Endogenous methanogenesis stimulates oxidation of atmospheric CH(4) in alpine tundra soil.	2002-05	12043000
Voltammetric studies of the interaction of lumazine with cyclodextrins and DNA.	2002-04-15	11929664
Quantitative analysis of the behavior of Dictyostelium discoideum amoebae: stringency of pteridine reception.	2002-01	11810695
Design, synthesis, and evaluation of 9-D-ribityl-1,3,7-trihydro-2,6,8-purinetrione, a potent inhibitor of riboflavin synthase and lumazine synthase.	2001-12-14	11735509
Reaction of superoxide and nitric oxide with peroxynitrite. Implications for peroxynitrite-mediated oxidation reactions in vivo.	2001-08-03	11373284
Riboflavin synthesis genes ribE, ribB, ribH, ribA reside in the lux operon of Photobacterium leiognathi.	2001-06-15	11396941
Biosynthesis of riboflavin. The reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without enzymatic catalysis under physiological conditions.	2001-04-20	11304170
Tautomeric energetics of xanthine oxidase substrates: xanthine, 2-oxo-6-methylpurine, and lumazine.	2001-03	11330474
Reactive oxygen and nitrogen metabolites modulate fibronectin-induced fibroblast migration in vitro.	2001-01-01	11134892
Biosynthesis of riboflavin.	2001	11153262

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:18:48 GMT 2025` Edited by `admin` on `Mon Mar 31 21:18:48 GMT 2025`
Record UNII	260MF9U4WC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-225113

Preferred Name

English

LUMAZINE

Common Name

English

NSC-41801

Code

English

2,4(1H,3H)-PTERIDINEDIONE

Systematic Name

English

2,4-DIHYDROXYPTERIDINE

Systematic Name

English

2,4-PTERIDINEDIOL

Systematic Name

English

LUMAZIN

Common Name

English

LUMAZINE [MI]

Common Name

English

PTERIDINE-2,4-DIONE

Systematic Name

English

Code System Code Type Description

FDA UNII

260MF9U4WC