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

Molecular Formula	C13H12N4O2
Molecular Weight	256.26
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
Photophysical properties of lumichromes in water.	2001 Jul	11470567
Transport functions of riboflavin carriers in the rat small intestine and colon: site difference and effects of tricyclic-type drugs.	2001 Jul-Aug	11570591
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 Jun	11388904
Further computational studies on the conformation of 1,5-dihydrolumiflavin.	2001 Oct	11761324
Vibration spectroscopy reveals light-induced chromophore and protein structural changes in the LOV2 domain of the plant blue-light receptor phototropin 1.	2002 Jun 11	12044148
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 Jun 19	12059249
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 Oct	12382053
The role of aromaticity in the planarity of lumiflavin.	2002 Sep 6	12201752
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 Aug	12966080
Monoamine oxidase A inhibitory potency and flavin perturbation are influenced by different aspects of pirlindole inhibitor structure.	2003 Jun 1	12781338
Flavin catalyzed oxidations of sulfides and amines with molecular oxygen.	2003 Mar 12	12617641
Photolysis of riboflavin in aqueous solution: a kinetic study.	2004 Aug 6	15265559
Chromatographic study of photolysis of aqueous cyanocobalamin solution in presence of vitamins B and C.	2004 Jan	16414582
Riboflavin uptake and FAD synthesis in Saccharomyces cerevisiae mitochondria: involvement of the Flx1p carrier in FAD export.	2004 Jan 2	14555654
Identification and functional characterization of riboflavin transporter in human-derived retinoblastoma cell line (Y-79): mechanisms of cellular uptake and translocation.	2005 Aug	16117691
Mechanism of riboflavin uptake by cultured human retinal pigment epithelial ARPE-19 cells: possible regulation by an intracellular Ca2+-calmodulin-mediated pathway.	2005 Jul 15	15878949
Use of abasic site-containing DNA for electrochemical SNPs detection.	2006	17150832
Effect of light intensity and wavelengths on photodegradation reactions of riboflavin in aqueous solution.	2006 Jan 2	16223586
Photolysis of formylmethylflavin in aqueous and organic solvents.	2006 Jul	16820855
Effects of riboflavin on the phototransformation of benzo[a]pyrene.	2006 May	16289229
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 Nov	16944231
Quantum mechanical study of photoinduced charge transfer in FMN binding protein.	2008 Dec 11	19053889
Luminescence quenching by reversible ionization or exciplex formation/dissociation.	2008 Nov 20	18956831
ESR study of the singlet oxygen quenching and protective activity of Trolox on the photodecomposition of riboflavin and lumiflavin in aqueous buffer solutions.	2009 Aug	19723181
Small-molecule binding at an abasic site of DNA: strong binding of lumiflavin for improved recognition of thymine-related single nucleotide polymorphisms.	2009 Feb 5	19175344
Primary reactions of the LOV2 domain of phototropin studied with ultrafast mid-infrared spectroscopy and quantum chemistry.	2009 Jul 8	19580760
Influence of the LOV domain on low-lying excited states of flavin: a combined quantum-mechanics/molecular-mechanics investigation.	2009 Nov 26	19891470
Mechanism of N(5)-ethyl-flavinium cation formation upon electrochemical oxidation of N(5)-ethyl-4a-hydroxyflavin pseudobase.	2010 Jul 29	20597524
Effect of divalent anions on photodegradation kinetics and pathways of riboflavin in aqueous solution.	2010 May 10	20138130
Improved density functional description of the electrochemistry and structure-property descriptors of substituted flavins.	2010 Nov 25	20961131

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:09:40 GMT 2023` Edited by `admin` on `Fri Dec 15 19:09:40 GMT 2023`
Record UNII	4M2669414M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

7,8,10-TRIMETHYLISOALLOXAZINE

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