1-deoxy-1-(7-hydroxy-6-methyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl)-D-ribitol
Basic information
- CAS
2184-54-5- Standard SMILES
Cc1nc2c(=O)[nH]c(=O)[nH]c2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1=O- InChIKey
QCYVUUAIJUUUPI-BBVRLYRLSA-N- Molecular formula
- C12H16N4O7
- Average molar mass
- 328.28 g/mol
- Monoisotopic mass
- 328.10189886
Overview
7-hydroxy-6-methyl-8-(1-D-ribityl)lumazine is the pteridine that is lumazine substituted with a methyl group at C-6, a hydroxy group at C-7 and a 1-D-ribityl group at N-8. It has a role as an EC 2.5.1.9 (riboflavin synthase) inhibitor. It is functionally related to a ribitol and a lumazine. It is a conjugate acid of a 7-hydroxy-6-methyl-8-(1-D-ribityl)lumazine(1-).
Names & identifiers
- Preferred name
- 1-deoxy-1-(7-hydroxy-6-methyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl)-D-ribitol
- IUPAC
- 6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1H-pteridine-2,4,7-trione
- English name
- 7-hydroxy-6-methyl-8-(1-D-ribityl)lumazine
- Molecular formula
- C12H16N4O7
- Molecular weight
- 328.28
Names & synonyms
1-deoxy-1-(7-hydroxy-6-methyl-2,4-dioxo-3,4-dihydropteridin-8(2H)-yl)-D-ribitol6-methyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1H-pteridine-2,4,7-trione6-methyl-8-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)-1H-pteridine-2,4,7-trioneRefChem:935069RL-6-Me-7-OH2184-54-57-Hydroxy-6-methyl-8-(1-D-ribityl)lumazine7-hydroxy-6-methyl-8-D-ribityllumazineCHEBI:27581Masuda's compound V1-deoxy-1-(3,4-dihydro-7-hydroxy-6-methyl-2,4-dioxo-8(2H)-pteridinyl)-D-Ribitol6-methyl-7-oxo-8-(1-D-ribityl)lumazine
Show more names
D-Ribitol, 1-deoxy-1-(3,4-dihydro-7-hydroxy-6-methyl-2,4-dioxo-8(2H)-pteridinyl)-7-Hydroxy-6-Methyl-8-((2S,3S,4R)-2,3,4,5-Tetrahydroxypentyl)Pteridine-2,4(3H,8H)-Dione7-Hydroxy-6-Methyl-8-((2S,3S,4R)-2,3,4,5-Tetrahydroxypentyl)Pteridine-2,4(3H,8H)-Dione(WX142001)
1VY7-Hydroxy-6-methyl-8-ribityl lumazine4l4vEpitope ID:178095SCHEMBL11754109SCHEMBL15603800SCHEMBL31673745CHEBI:60900
Properties
Computed structural properties
- XLogP
- -4.1
- Topological polar surface area
- 172 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 615
Physicochemical properties
- Melting point
- 263 °C · 263 °C (decomp)
- Density
- 1.889 · 1.889±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 9.101 · 9.101±0.70(predicted)
- form
- Solid
- color
- Light yellow to yellow
Chemistry & industry
Applications
UsesRL-6-Me-7-OH is a hapten that activates human and mouse MAIT cells (EC50=25μM). RL-6-Me-7-OH can be combined with carrier proteins and used in antigen design. RL-6-Me-7-OH can be used in inflammation and immunity research[1].
Additional notes
DefinitionChEBI: 7-hydroxy-6-methyl-8-(1-D-ribityl)lumazine is the pteridine that is lumazine substituted with a methyl group at C-6, a hydroxy group at C-7 and a 1-D-ribityl group at N-8. It has a role as an EC 2.5.1.9 (riboflavin synthase) inhibitor. It is functionally related to a lumazine and a ribitol.
Related reactions
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Compound notes
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