1-Deoxy-1-(8-(dimethylamino)-4-hydroxy-7-methyl-2-oxobenzo(g)pteridin-10(2H)-yl)pentitol
Basic information
- CAS
51093-55-1- Standard SMILES
Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(CC(O)C(O)C(O)CO)c2cc1N(C)C- InChIKey
IGQLDUYTWDABFK-UHFFFAOYSA-N- Molecular formula
- C18H23N5O6
- Average molar mass
- 405.4 g/mol
- Monoisotopic mass
- 405.16483347
Overview
See also: 8-Demethyl-8-(dimethylamino)riboflavin (annotation moved to).
Names & identifiers
- Preferred name
- 1-Deoxy-1-(8-(dimethylamino)-4-hydroxy-7-methyl-2-oxobenzo(g)pteridin-10(2H)-yl)pentitol
- IUPAC
- 8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4-dione
- English name
- Roseoflavin
- Molecular formula
- C18H23N5O6
- Molecular weight
- 405.41
Names & synonyms
DTXSID609653681-Deoxy-1-(8-(dimethylamino)-4-hydroxy-7-methyl-2-oxobenzo(g)pteridin-10(2H)-yl)pentitol1-Deoxy-1-[8-(dimethylamino)-4-hydroxy-7-methyl-2-oxobenzo[g]pteridin-10(2H)-yl]pentitolRefChem:1055343DTXCID001393038Roseoflavine8-(dimethylamino)-7-methyl-10-(2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4-dioneRoseoflavin?Riboflavin, 8-demethyl-8-(dimethylamino)-SCHEMBL22034370AKOS030255955NS00018036
Show more names
RoseoflavinRoseoflavin, 10 mM in DMSO8-Demethyl-8-(dimethylamino)riboflavin8-demethyl-8-(dimethylamino)-riboflavi8-DiMethylaMinoriboflavin, Roseoflavine8-(Dimethylamino)-7-methyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dionepigment,bacteria,resistant,Inhibitor,RNA,riboswitch,ligand,analog,antimicrobial,Bacterial,Roseoflavin,inhibit
Q1768219
Properties
Computed structural properties
- XLogP
- -1.7
- Topological polar surface area
- 158 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 726
Physicochemical properties
- Melting point
- 276 · 276-278°C
- Density
- 1.59 · 1.59±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- powder
- pka
- 9.69 · 9.69±0.70(Predicted)
- color
- white to very dark brown
- Stability
- Light sensitive
- InChI
- 1S/C18H23N5O6/c1-8-4-9-11(5-10(8)22(2)3)23(6-12(25)15(27)13(26)7-24)16-14(19-9)17(28)21-18(29)20-16/h4-5,12-13,15,24-27H,6-7H2,1-3H3,(H,21,28,29)
- InChIKey
- IGQLDUYTWDABFK-UHFFFAOYSA-N
- SMILES
- [n]1(c2n[c]([nH][c](c2nc3c1cc(c(c3)C)N(C)C)=O)=O)CC(O)C(O)C(O)CO
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesHas weak antibacterial activity against some gram-positive bacteria, especially Staphylococcus aureus, Sarcina latea, Bacillus cereus, and Bacillus subtilis. Also exhibits antiriboflavin activity and inhibits the biosynthesis of riboflavin by a r
UsesAn analog known to compete with Riboflavin in Lactobacillus casei. Riboflavin kinase substrate and inhibitor
UsesRoseoflavin is an antibacterial pigment isolated from Streptomyces davawensis as an anti-metabolite of riboflavin. Roseoflavin is used as a substrate to mimic riboflavin in flavin biosynthesis, but leading to the formation of inactive flavin co-factors. More recently, roseoflavin has been shown to be an important regulator of bacterial gene expression by binding to untranslated regions of RNA, so-called ribo-switching sites.
Additional notes
DefinitionChEBI: A benzopteridine that is riboflavin in which the methyl group at position 8 is substituted by a dimethylamino group.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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