LUMIFLAVINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H12N4O2
Molecular Weight	256.26
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=NC(=O)NC(=O)C2=NC3=C1C=C(C)C(C)=C3

InChI

InChIKey=KPDQZGKJTJRBGU-UHFFFAOYSA-N

InChI=1S/C13H12N4O2/c1-6-4-8-9(5-7(6)2)17(3)11-10(14-8)12(18)16-13(19)15-11/h4-5H,1-3H3,(H,16,18,19)

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Improved density functional description of the electrochemistry and structure-property descriptors of substituted flavins.	2010-11-25	20961131
Mechanism of N(5)-ethyl-flavinium cation formation upon electrochemical oxidation of N(5)-ethyl-4a-hydroxyflavin pseudobase.	2010-07-29	20597524
Effect of divalent anions on photodegradation kinetics and pathways of riboflavin in aqueous solution.	2010-05-10	20138130
Influence of the LOV domain on low-lying excited states of flavin: a combined quantum-mechanics/molecular-mechanics investigation.	2009-11-26	19891470
ESR study of the singlet oxygen quenching and protective activity of Trolox on the photodecomposition of riboflavin and lumiflavin in aqueous buffer solutions.	2009-08	19723181
Primary reactions of the LOV2 domain of phototropin studied with ultrafast mid-infrared spectroscopy and quantum chemistry.	2009-07-08	19580760
Charge redistribution in oxidized and semiquinone E. coli DNA photolyase upon photoexcitation: stark spectroscopy reveals a rationale for the position of Trp382.	2009-04-08	19292445
Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine.	2009-04-01	19254841
Identification and functional characterization of rat riboflavin transporter 2.	2009-04	19122205
Small-molecule binding at an abasic site of DNA: strong binding of lumiflavin for improved recognition of thymine-related single nucleotide polymorphisms.	2009-02-05	19175344
Quantum mechanical study of photoinduced charge transfer in FMN binding protein.	2008-12-11	19053889
Luminescence quenching by reversible ionization or exciplex formation/dissociation.	2008-11-20	18956831
Effect of borate buffer on the photolysis of riboflavin in aqueous solution.	2008-11-13	18760621
Contributions of the 8-methyl group to the vibrational normal modes of flavin mononucleotide and its 5-methyl semiquinone radical.	2008-07-10	18547041
Femtosecond pump-probe experiments on trapped flavin: optical control of dissociation.	2008-02-21	18298175
Electronic transition dipole moment directions of reduced anionic flavin in stretched poly(vinyl alcohol) films.	2008-01-10	18069812
Combined quantum mechanical and molecular mechanical simulations of one- and two-electron reduction potentials of flavin cofactor in water, medium-chain acyl-CoA dehydrogenase, and cholesterol oxidase.	2007-07-05	17567113
Theoretical study of the electronic spectra of oxidized and reduced states of lumiflavin and its derivative.	2007-03	17226839
Efficient cycloreversion of cis,syn-thymine photodimer by a Zn2+ -1,4,7,10-tetraazacyclododecane complex bearing a lumiflavin and tryptophan by chemical reduction and photoreduction of a lumiflavin unit.	2006-11	16944231
Ultrafast vibrational spectroscopy of the flavin chromophore.	2006-10-19	17034182
Characteristic structure and environment in FAD cofactor of (6-4) photolyase along function revealed by resonance Raman spectroscopy.	2006-08-24	16913812
Photolysis of formylmethylflavin in aqueous and organic solvents.	2006-07	16820855
Electrochemical SNPs detection using an abasic site-containing DNA on a gold electrode.	2006-06-14	16733585
Theoretical study on charge-transfer interaction between acyl-CoA dehydrogenase and 3-thiaacyl-CoA using density functional method.	2006-05	16751592
Effects of riboflavin on the phototransformation of benzo[a]pyrene.	2006-05	16289229
Glycerate-oxidizing activity of glycolate oxidase from leaves of Spinacia oleracea.	2006-04	16622317
Dodecins: a family of lumichrome binding proteins.	2006-03-31	16460756
Photosensitizing effect of riboflavin, lumiflavin, and lumichrome on the generation of volatiles in soy milk.	2006-03-22	16536619
Effect of light intensity and wavelengths on photodegradation reactions of riboflavin in aqueous solution.	2006-01-02	16223586
Use of abasic site-containing DNA for electrochemical SNPs detection.	2006	17150832
Identification and functional characterization of riboflavin transporter in human-derived retinoblastoma cell line (Y-79): mechanisms of cellular uptake and translocation.	2005-08	16117691
Mechanism of riboflavin uptake by cultured human retinal pigment epithelial ARPE-19 cells: possible regulation by an intracellular Ca2+-calmodulin-mediated pathway.	2005-07-15	15878949
Photolysis of riboflavin in aqueous solution: a kinetic study.	2004-08-06	15265559
Riboflavin uptake and FAD synthesis in Saccharomyces cerevisiae mitochondria: involvement of the Flx1p carrier in FAD export.	2004-01-02	14555654
Chromatographic study of photolysis of aqueous cyanocobalamin solution in presence of vitamins B and C.	2004-01	16414582
Structure of the transition state analog of medium-chain acyl-CoA dehydrogenase. Crystallographic and molecular orbital studies on the charge-transfer complex of medium-chain acyl-CoA dehydrogenase with 3-thiaoctanoyl-CoA.	2003-08	12966080
Monoamine oxidase A inhibitory potency and flavin perturbation are influenced by different aspects of pirlindole inhibitor structure.	2003-06-01	12781338
Flavin catalyzed oxidations of sulfides and amines with molecular oxygen.	2003-03-12	12617641
Purification and characterization of the monooxygenase catalyzing sulfur-atom specific oxidation of dibenzothiophene and benzothiophene from the thermophilic bacterium Paenibacillus sp. strain A11-2.	2002-10	12382053
The role of aromaticity in the planarity of lumiflavin.	2002-09-06	12201752
The reaction of triplet flavin with indole. A study of the cascade of reactive intermediates using density functional theory and time resolved infrared spectroscopy.	2002-06-19	12059249
Vibration spectroscopy reveals light-induced chromophore and protein structural changes in the LOV2 domain of the plant blue-light receptor phototropin 1.	2002-06-11	12044148
Further computational studies on the conformation of 1,5-dihydrolumiflavin.	2001-10	11761324
Transport functions of riboflavin carriers in the rat small intestine and colon: site difference and effects of tricyclic-type drugs.	2001-09-26	11570591
Photophysical properties of lumichromes in water.	2001-07	11470567
Frontal gel chromatographic analysis of the interaction of a protein with self-associating ligands: aberrant saturation in the binding of flavins to bovine serum albumin.	2001-06	11388904

Patents

Name

Type

Language

7,8,10-TRIMETHYLISOALLOXAZINE

Preferred Name

English

LUMIFLAVINE

Common Name

English

LUMIFLAVINE [MI]

Common Name

English

BENZO(G)PTERIDINE-2,4(3H,10H)-DIONE, 7,8,10-TRIMETHYL-

Systematic Name

English

RIBOFLAVIN IMPURITY A [EP IMPURITY]

Common Name

English

BENZO(G)PTERIDIN-2(10H)-ONE, 4-HYDROXY-7,8,10-TRIMETHYL-

Systematic Name

English

7,8,10-TRIMETHYLBENZO(G)PTERIDINE-2,4(3H,10H)-DIONE

Systematic Name

English

LUMILACTOFLAVIN

Common Name

English

LUMIFLAVINE [USP IMPURITY]

Common Name

English

RIBOFLAVIN SODIUM PHOSPHATE IMPURITY E [EP IMPURITY]

Common Name

English

Code System Code Type Description

CAS

1088-56-8