LUMICHROME

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H10N4O2
Molecular Weight	242.2334
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC2=NC3=C(N=C2C=C1C)C(=O)NC(=O)N3

InChI

InChIKey=ZJTJUVIJVLLGSP-UHFFFAOYSA-N

InChI=1S/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)

HIDE SMILES / InChI

Molecular Formula	C12H10N4O2
Molecular Weight	242.2334
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
Lumichrome complexation by cyclodextrins: influence of pharmaceutical excipients.	2010-12	21284255
Effect of substituents of alloxazine derivatives on the selectivity and affinity for adenine in AP-site-containing DNA duplexes.	2010-11-07	20820650
Photophysical characterisation and photo-cycle dynamics of LOV1-His domain of phototropin from Chlamydomonas reinhardtii with roseoflavin monophosphate cofactor.	2010-10-05	20655238
Bicomponent hydrogels of lumichrome and melamine: photoluminescence property and its dependency on pH and temperature.	2010-09-09	20715827
Effect of divalent anions on photodegradation kinetics and pathways of riboflavin in aqueous solution.	2010-05-10	20138130
Theoretical determination of the redox potentials of NRH:quinone oxidoreductase 2 using quantum mechanical/molecular mechanical simulations.	2009-06-11	19445526
Dodecin is the key player in flavin homeostasis of archaea.	2009-05-08	19224924
Calculating solution redox free energies with ab initio quantum mechanical/molecular mechanical minimum free energy path method.	2009-04-28	19405565
Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine.	2009-04-01	19254841
(1)H and (13)C NMR assignments of eight nitrogen containing compounds from Nocardia alba sp.nov (YIM 30243(T)).	2009-04	19165845
Effect of borate buffer on the photolysis of riboflavin in aqueous solution.	2008-11-13	18760621
Nod factor [Nod Bj V (C(18:1), MeFuc)] and lumichrome enhance photosynthesis and growth of corn and soybean.	2008-09-08	18190997
The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum-sensing receptor.	2008-09	18700823
Toxicity testing of a novel riboflavin-based technology for pathogen reduction and white blood cell inactivation.	2008-04	18353253
Femtosecond pump-probe experiments on trapped flavin: optical control of dissociation.	2008-02-21	18298175
Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.	2008-01	17804027
Competitive binding of small ligands to nucleobases in AP site-containing DNA duplexes.	2008	18776282
Electron ionisation and electrospray ionisation mass spectrometric study of a series of isomeric methyl-, dimethyl- and trimethylalloxazines.	2008	18183634
Oxygen uptake after electron transfer from amines, amino acids and ascorbic acid to triplet flavins in air-saturated aqueous solution.	2007-05-25	17395476
Photolysis of formylmethylflavin in aqueous and organic solvents.	2006-07	16820855
Photodynamics of the small BLUF protein BlrB from Rhodobacter sphaeroides.	2006-06-01	16495071
Effects of riboflavin on the phototransformation of benzo[a]pyrene.	2006-05	16289229
In search of excited-state proton transfer in the lumichrome dimer in the solid state: theoretical and experimental approach.	2006-04-13	16599430
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
Ground- and excited-state double proton transfer in lumichrome/acetic acid system: theoretical and experimental approach.	2005-12-29	16366620
The ferredoxin-NADP(H) reductase from Rhodobacter capsulatus: molecular structure and catalytic mechanism.	2005-09-06	16128574
Identification and functional characterization of riboflavin transporter in human-derived retinoblastoma cell line (Y-79): mechanisms of cellular uptake and translocation.	2005-08	16117691
Nod factor enhances calcium uptake by soybean.	2005-07-29	17092733
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
The rhizosphere signal molecule lumichrome alters seedling development in both legumes and cereals.	2005-05	15819908
Hydrogen-bonded complexes of lumichrome.	2005-03-10	16833507
Effect of phosphate buffer on photodegradation reactions of riboflavin in aqueous solution.	2005-03-01	15708520
Xylem transport and shoot accumulation of lumichrome, a newly recognized rhizobial signal, alters root respiration, stomatal conductance, leaf transpiration and photosynthetic rates in legumes and cereals.	2005-03	15720696
Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. I. Taxonomy, fermentation, isolation and biological activities.	2005-02	15835721
Separation, identification and quantification of riboflavin and its photoproducts in blood products using high-performance liquid chromatography with fluorescence detection: a method to support pathogen reduction technology.	2004-09-24	15382964
Photolysis of riboflavin in aqueous solution: a kinetic study.	2004-08-06	15265559
A study of simultaneous photolysis and photoaddition reactions of riboflavin in aqueous solution.	2004-07-19	15246345
A new indolinepeptide from Paecilomyces sp. J300.	2004-06	15283460
Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin.	2004-02-17	14769034
Chromatographic study of photolysis of aqueous cyanocobalamin solution in presence of vitamins B and C.	2004-01	16414582
Comparison of the voltammetric studies at mercury and glassy carbon electrodes for the interaction of lumichrome with DNA and analytical applications.	2003-04	12733014
Pathogen inactivation of blood components: current status and introduction of an approach using riboflavin as a photosensitizer.	2002-08	12430933
Substrate binding to DNA photolyase studied by electron paramagnetic resonance spectroscopy.	2001-08	11463661
Photophysical properties of lumichromes in water.	2001-07	11470567
The electronic structure of the flavin cofactor in DNA photolyase.	2001-04-25	11457111
Structure of human biliverdin IXbeta reductase, an early fetal bilirubin IXbeta producing enzyme.	2001-03	11224564
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.	1982-02-15	6802140

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:33:54 GMT 2025` Edited by `admin` on `Mon Mar 31 19:33:54 GMT 2025`
Record UNII	99U1UDJ2HM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUMICHROME

Common Name

English

NSC-96911

Preferred Name

English

7,8-DIMETHYLALLOXAZINE

Common Name

English

BENZO(G)PTERIDINE-2,4(1H,3H)-DIONE, 7,8-DIMETHYL-

Systematic Name

English

7,8-DIMETHYLISOALLOXAZINE

Systematic Name

English

RIBOFLAVIN LUMICHROME

Common Name

English

LUMICHROME [MI]

Common Name

English

RIBOFLAVIN IMPURITY B [EP IMPURITY]

Common Name

English

ALLOXAZINE, 7,8-DIMETHYL-

Systematic Name

English

7,8-DIMETHYLBENZO(G)PTERIDINE-2,4-(1H,3H)-DIONE

Common Name

English

Code System Code Type Description

CAS

1086-80-2