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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-16 22:25:45 UTC
Update Date2017-10-23 19:05:45 UTC
HMDB IDHMDB0011106
Secondary Accession Numbers
  • HMDB11106
Metabolite Identification
Common Name5-Amino-6-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 color and in addition to being used as a food coloring 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
Thumb
Synonyms
ValueSource
1-[(5-amino-2,6-Dihydroxypyrimidin-4-yl)amino]-1-deoxy-D-ribitolHMDB
1-[(5-amino-2,6-dioxo-1,2,3,6-Tetrahydropyrimidin-4-yl)amino]-1-deoxy-D-ribitolHMDB
4-(1-D-ribitylamino)-5-amino-2,6 DihydroxypyrimidineHMDB
4-(1-D-ribitylamino)-5-amino-2,6-DihydroxypyrimidineHMDB
4-(1-D-ribitylamino)-5-AminouracilHMDB
5-amino-6-(2,3,4,5-tetrahydroxypentylamino)-1H-Pyrimidine-2,4-dioneHMDB
6-ribitylamino-5-AminouracilHMDB
Chemical FormulaC9H16N4O6
Average Molecular Weight276.2465
Monoisotopic Molecular Weight276.106984264
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 NumberNot Available
SMILES
NC1=C(NCC(O)C(O)C(O)CO)NC(=O)NC1=O
InChI Identifier
InChI=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)
InChI KeyXKQZIXVJVUPORE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidone
  • Hydropyrimidine
  • Primary aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Polyol
  • Azacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-2.4ALOGPS
logP-4.4ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)4.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area177.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.48 m³·mol⁻¹ChemAxon
Polarizability25.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0903-9440000000-d4b6a6cff43cc761315fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-056r-6294350000-61d4d076b5309ed14bcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-1190000000-2514b630f375b2189bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08fu-9750000000-779ce19c1a0e6b0c6932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-2f9fc8d8f57a4b3ca8c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01x0-5490000000-40e672b419cf2a89e723View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9210000000-e4e8a4b406ad4dfd459fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-0e769fc743b8cee3b542View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027889
KNApSAcK IDNot Available
Chemspider ID216
KEGG Compound IDC04732
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound221
PDB IDNot Available
ChEBI ID15934
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. WACKER H, HARVEY RA, WINESTOCK CH, PLAUT GW: 4-(1'-D-RIBITYLAMINO)-5-AMINO-2,6-DIHYDROXYPYRIMIDINE, THE SECOND PRODUCT OF THE RIBOFLAVIN SYNTHETASE REACTION. J Biol Chem. 1964 Oct;239:3493-7. [PubMed:14245407 ]

Enzymes

General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available