6,7-Dimethyl-8-ribityllumazine

HCID 168989CAS 2535-20-8

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Grundinformationen

Standard-SMILES: Cc1nc2c(=O)[nH]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C
InChIKey: SXDXRJZUAJBNFL-XKSSXDPKSA-N
Summenformel: C13H18N4O6
Durchschnittliche Molmasse: 326,31 g/mol
Monoisotopische Masse: 326,1226343

Überblick

6,7-dimethyl-8-(1-D-ribityl)lumazine is the pteridine that is lumazine substituted with methyl groups at C-6 and -7 and with a 1-D-ribityl group on N-8. It has a role as a cofactor and an Escherichia coli metabolite. It is functionally related to a ribitol and a lumazine. It is a conjugate acid of a 6,7-dimethyl-8-(1-D-ribityl)lumazine(1-).

Namen und Bezeichner

Bevorzugter Name: 6,7-Dimethyl-8-ribityllumazine
IUPAC: 6,7-dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridine-2,4-dione
Englischer Name: Russupteridine IV
Summenformel: C13H18N4O6
Molmasse: 326.31

Namen und Synonyme

6,7-Dimethyl-8-ribityllumazine6,7-dimethyl-8-(1-D-ribityl)lumazineRussupteridine IV6,7-dimethyl-8-(D-ribityl)lumazineRL-6,7-diMeO1DSD0WC7M6,7-dimethyl-8-D-ribityllumazineCHEBI:17601UNII-O1DSD0WC7MRiboflavin impurity C [EP]DTXSID90199199RIBOFLAVIN IMPURITY C [EP IMPURITY]

Weitere Namen anzeigen

6,7-DimethylribitylVitamin B2 Impurity CRiboflavin EP Impurity C6,7-DiMethylriboluMazineRussupteridine IV Impurity6,7-DiMethylribityl LuMazineRiboflavin(VB2) EP Impurity C6,7-DiMethyl-8-(1'-D-ribityl)luMazine

1-Deoxy-1-(3,4-dihydro-6,7-dimethyl-2,4-dioxo-8(2H)-pteridinyl)-ribitolRibitol, 1-deoxy-1-(3,4-dihydro-6,7-dimethyl-2,4-dioxo-8(2H)-pteridinyl)-D-RIBITOL, 1-DEOXY-1-(3,4-DIHYDRO-6,7-DIMETHYL-2,4-DIOXO-8(2H)-PTERIDINYL)-RIBOFLAVIN IMPURITY C (EP IMPURITY)Riboflavin impurity CRefChem:103865DTXCID701216906,7-Dimethyl-8-ribityllumazine, (D)-isomer

Datenbank-Bezeichner

CAS: 2535-20-8、5118-16-1
PubChem CID: 168989
DTXSID: DTXSID90199199
ChEBI: CHEBI:17601
UNII: O1DSD0WC7M
Nikkaji: J643.571H

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -2,7
Polarare Oberfläche (TPSA): 155 Å²
H-Brücken-Donoren: 5
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 5
Schwere Atome: 23
Formalladung: 0
Komplexität: 626

Experimentelle und physikochemische Eigenschaften

LogP-3.145

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 272 · 272-274 °C (decomp)
Dichte: 1.7 · 1.70±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
Löslichkeit: DMSO (Slightly), Water (Slightly)
pka: 9.39 · 9.39±0.70(Predicted)
Aggregatzustand: Solid
Farbe: Dark Yellow to Very Dark Brown
Stabilität: Light Sensitive
InChI: InChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1
InChIKey: SXDXRJZUAJBNFL-XKSSXDPKSA-N
SMILES: C(N1C(=C(N=C2C(NC(N=C12)=O)=O)C)C)[C@H](O)[C@H](O)[C@H](O)CO

Sicherheit und Regulatorisches

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

Metabolite PathwaysRiboflavin Metabolism

Anwendungen · 2 Einträge

Beschreibung6,7-dimethyl-8-Ribityllumazine (DMRL) is a natural chromophore of lumazine protein (LumP), a fluorescent accessory protein that induces a blue shift (495 to 475 nm) in luciferase emission wavelengths in bioluminescent Photobacterium. DMRL binds noncovalently to both the N- and C-terminal domains of LumP. It is also a biosynthetic precursor of riboflavin and substrate of riboflavin synthase.

Verwenden6,7-Dimethyl-8-ribityllumazine serves as fluorophore in Lumazine (L473800) proteins (LumP) of luminescent bacteria.