CAS 2535-20-8 6,7-Dimethyl-8-ribityllumazine (HCID 168989)

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Basic information

CAS: 2535-20-8
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
Molecular formula: C13H18N4O6
Average molar mass: 326.31 g/mol
Monoisotopic mass: 326.1226343

Overview

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-).

Names & identifiers

Preferred name: 6,7-Dimethyl-8-ribityllumazine
IUPAC: 6,7-dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]pteridine-2,4-dione
English name: Russupteridine IV
Molecular formula: C13H18N4O6
Molecular weight: 326.31

Names & synonyms

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]

Show more names

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

Database identifiers

Properties

Computed structural properties

XLogP: -2.7
Topological polar surface area: 155 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 7
Rotatable bonds: 5
Heavy atoms: 23
Formal charge: 0
Complexity: 626

Experimental & physicochemical properties

LogP-3.145

Physical DescriptionSolid

Physicochemical properties

Melting point: 272 · 272-274 °C (decomp)
Density: 1.7 · 1.70±0.1 g/cm3(Predicted)
storage temp.: -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
solubility: DMSO (Slightly), Water (Slightly)
pka: 9.39 · 9.39±0.70(Predicted)
form: Solid
color: Dark Yellow to Very Dark Brown
Stability: 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

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Chemistry & industry

Pharmacology

Metabolite PathwaysRiboflavin Metabolism

Applications · 2 items

Description6,7-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.

Uses6,7-Dimethyl-8-ribityllumazine serves as fluorophore in Lumazine (L473800) proteins (LumP) of luminescent bacteria.