Common Name5-amino-6-(d-ribitylamino)uracil
Description5-Amino-6-ribitylamino uracil is an intermediate in riboflavin metabolism. It is converted from 5-amino-6-(5'-phosphoribitylamino)uracil via dephosphorylation by the enzyme phosphohistidine phosphatase 1 (EC 3.1.3.-). It is considered to be the second product of the riboflavin synthase reaction (PMID: 14245407 ). Humans do not have all the enzymes needed to synthesize or metabolize riboflavin. However, gut microflora do have the necessary enzymatic machinery to produce and metabolize this vitamin. Riboflavin (or vitamin B2) is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. It is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. Riboflavin is yellow or yellow-orange in colour and in addition to being used as a food colouring it is also used to fortify some foods including baby foods, breakfast cereals, pastas, sauces, processed cheese, fruit drinks, vitamin-enriched milk products, some energy drinks, and vitamin supplements.
Structure
Molecular FormulaC9H16N4O6
Average Mass276.24650
Monoisotopic Mass276.10698
IUPAC Name5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Name5-amino-6-[(2,3,4,5-tetrahydroxypentyl)amino]-1,3-dihydropyrimidine-2,4-dione
CAS Registry Number17014-74-3
SMILESNc1c(NC[C@H](O)[C@H](O)[C@H](O)CO)[nH]c(=O)[nH]c1=O
InChI IdentifierInChI=1S/C9H16N4O6/c10-5-7(12-9(19)13-8(5)18)11-1-3(15)6(17)4(16)2-14/h3-4,6,14-17H,1-2,10H2,(H3,11,12,13,18,19)/t3-,4+,6-/m0/s1
InChI KeyXKQZIXVJVUPORE-RPDRRWSUSA-N
CHEBI IDCHEBI:15934
HMDB IDHMDB0011106
StateSolid
Water Solubility1.43e+01 g/l
logP-2.44
logS-1.29
pKa (Strongest Acidic)9.41
pKa (Strongest Basic)4.36
Hydrogen Acceptor Count8
Hydrogen Donor Count8
Polar Surface Area177.17 Ų
Rotatable Bond Count6
Physiological Charge0
Formal Charge0
Refractivity71.48 m³·mol⁻¹
Polarizability25.92

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