Common Name6,7-dimethyl-8-(1-d-ribityl)lumazine
Description6,7-Dimethyl-8-(1-D-ribityl)lumazine belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is an extremely weak basic (essentially neutral) compound (based on its pKa). 6,7-Dimethyl-8-(1-D-ribityl)lumazine exists in all living organisms, ranging from bacteria to humans. In humans, 6,7-dimethyl-8-(1-D-ribityl)lumazine is involved in riboflavin metabolism. Outside of the human body, 6,7-dimethyl-8-(1-D-ribityl)lumazine has been detected, but not quantified in, several different foods, such as quinoa, arrowhead, conchs, watermelons, and Elliott's blueberries. This could make 6,7-dimethyl-8-(1-D-ribityl)lumazine a potential biomarker for the consumption of these foods. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is an intermediate in riboflavin metabolism. 6,7-Dimethyl-8-(1-D-ribityl)lumazine is the second to last step in the synthesis of ribitol and is converted from 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine via the enzyme riboflavin synthase beta chain. It is then converted into riboflavin via the enzyme riboflavin synthase alpha chain (EC 2.5.1.9).
Structure
Molecular FormulaC13H18N4O6
Average Mass326.30520
Monoisotopic Mass326.12263
IUPAC Name6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-2,3,4,8-tetrahydropteridine-2,4-dione
Traditional Name6,7-dimethyl-8-(2,3,4,5-tetrahydroxypentyl)-3h-pteridine-2,4-dione
CAS Registry Number2535-20-8
SMILESCc1nc2c(=O)[n-]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C
InChI IdentifierInChI=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
InChI KeySXDXRJZUAJBNFL-XKSSXDPKSA-N
CHEBI IDCHEBI:58201
HMDB IDHMDB0003826
Pathways
NameSMPDB/PathBank
Riboflavin Metabolism
StateSolid
Water Solubility1.23e+00 g/l
logP-1.84
logS-2.42
pKa (Strongest Acidic)6.97
pKa (Strongest Basic)-1.21
Hydrogen Acceptor Count9
Hydrogen Donor Count5
Polar Surface Area155.05 Ų
Rotatable Bond Count5
Physiological Charge-1
Formal Charge0
Refractivity79.00 m³·mol⁻¹
Polarizability31.53

We require the use of cookies for essential features like storing your previously submitted BASys2 queries. Rejecting the usage of cookies will result in certain features being disabled. By clicking ACCEPT or continuing to use the website you are agreeing to our use of cookies.

ACCEPT