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=C(C)C=C2N=C3C(=O)NC(=O)NC3=NC2=C1

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
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.	1982 Feb 15	6802140
The electronic structure of the flavin cofactor in DNA photolyase.	2001 Apr 25	11457111
Substrate binding to DNA photolyase studied by electron paramagnetic resonance spectroscopy.	2001 Aug	11463661
Photophysical properties of lumichromes in water.	2001 Jul	11470567
Structure of human biliverdin IXbeta reductase, an early fetal bilirubin IXbeta producing enzyme.	2001 Mar	11224564
Pathogen inactivation of blood components: current status and introduction of an approach using riboflavin as a photosensitizer.	2002 Aug	12430933
Comparison of the voltammetric studies at mercury and glassy carbon electrodes for the interaction of lumichrome with DNA and analytical applications.	2003 Apr	12733014
Photolysis of riboflavin in aqueous solution: a kinetic study.	2004 Aug 6	15265559
Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin.	2004 Feb 17	14769034
Chromatographic study of photolysis of aqueous cyanocobalamin solution in presence of vitamins B and C.	2004 Jan	16414582
A study of simultaneous photolysis and photoaddition reactions of riboflavin in aqueous solution.	2004 Jul 19	15246345
A new indolinepeptide from Paecilomyces sp. J300.	2004 Jun	15283460
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 Nov-Dec	15382964
Identification and functional characterization of riboflavin transporter in human-derived retinoblastoma cell line (Y-79): mechanisms of cellular uptake and translocation.	2005 Aug	16117691
Ground- and excited-state double proton transfer in lumichrome/acetic acid system: theoretical and experimental approach.	2005 Dec 29	16366620
Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. I. Taxonomy, fermentation, isolation and biological activities.	2005 Feb	15835721
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
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 Mar	15720696
Effect of phosphate buffer on photodegradation reactions of riboflavin in aqueous solution.	2005 Mar 1	15708520
Hydrogen-bonded complexes of lumichrome.	2005 Mar 10	16833507
The rhizosphere signal molecule lumichrome alters seedling development in both legumes and cereals.	2005 May	15819908
The ferredoxin-NADP(H) reductase from Rhodobacter capsulatus: molecular structure and catalytic mechanism.	2005 Sep 6	16128574
In search of excited-state proton transfer in the lumichrome dimer in the solid state: theoretical and experimental approach.	2006 Apr 13	16599430
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
Photodynamics of the small BLUF protein BlrB from Rhodobacter sphaeroides.	2006 Jun 1	16495071
Photosensitizing effect of riboflavin, lumiflavin, and lumichrome on the generation of volatiles in soy milk.	2006 Mar 22	16536619
Dodecins: a family of lumichrome binding proteins.	2006 Mar 31	16460756
Effects of riboflavin on the phototransformation of benzo[a]pyrene.	2006 May	16289229
Nod factor enhances calcium uptake by soybean.	2006 Nov-Dec	17092733
Oxygen uptake after electron transfer from amines, amino acids and ascorbic acid to triplet flavins in air-saturated aqueous solution.	2007 May 25	17395476
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
Toxicity testing of a novel riboflavin-based technology for pathogen reduction and white blood cell inactivation.	2008 Apr	18353253
Femtosecond pump-probe experiments on trapped flavin: optical control of dissociation.	2008 Feb 21	18298175
Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.	2008 Jan	17804027
Effect of borate buffer on the photolysis of riboflavin in aqueous solution.	2008 Nov 13	18760621
The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum-sensing receptor.	2008 Sep	18700823
Nod factor [Nod Bj V (C(18:1), MeFuc)] and lumichrome enhance photosynthesis and growth of corn and soybean.	2008 Sep 8	18190997
(1)H and (13)C NMR assignments of eight nitrogen containing compounds from Nocardia alba sp.nov (YIM 30243(T)).	2009 Apr	19165845
Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine.	2009 Apr 1	19254841
Calculating solution redox free energies with ab initio quantum mechanical/molecular mechanical minimum free energy path method.	2009 Apr 28	19405565
Theoretical determination of the redox potentials of NRH:quinone oxidoreductase 2 using quantum mechanical/molecular mechanical simulations.	2009 Jun 11	19445526
Dodecin is the key player in flavin homeostasis of archaea.	2009 May 8	19224924
Lumichrome complexation by cyclodextrins: influence of pharmaceutical excipients.	2010 Dec	21284255
Effect of divalent anions on photodegradation kinetics and pathways of riboflavin in aqueous solution.	2010 May 10	20138130
Effect of substituents of alloxazine derivatives on the selectivity and affinity for adenine in AP-site-containing DNA duplexes.	2010 Nov 7	20820650
Photophysical characterisation and photo-cycle dynamics of LOV1-His domain of phototropin from Chlamydomonas reinhardtii with roseoflavin monophosphate cofactor.	2010 Oct 5	20655238
Bicomponent hydrogels of lumichrome and melamine: photoluminescence property and its dependency on pH and temperature.	2010 Sep 9	20715827

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:09:38 GMT 2023` Edited by `admin` on `Fri Dec 15 19:09:38 GMT 2023`
Record UNII	99U1UDJ2HM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUMICHROME

Common 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

NSC-96911

Code

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