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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 05:44:14 UTC
Update Date2020-03-10 15:38:26 UTC
HMDB IDHMDB0003841
Secondary Accession Numbers
  • HMDB03841
Metabolite Identification
Common Name5-Amino-6-(5'-phosphoribitylamino)uracil
Description5-Amino-6-(5'-phosphoribitylamino)uracil belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. 5-Amino-6-(5'-phosphoribitylamino)uracil is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Amino-6-(5'-phosphoribitylamino)uracil has been detected, but not quantified in, several different foods, such as sapodilla, kumquats, sacred lotus, Persian limes, and Cascade huckleberries. This could make 5-amino-6-(5'-phosphoribitylamino)uracil a potential biomarker for the consumption of these foods. 5-Amino-6-(5'-phosphoribitylamino)uracil is an intermediate in riboflavin metabolism. 5-Amino-6-(5'-phosphoribitylamino)uracil is the third to last step in the synthesis of 7-hydroxy-6-methyl-8-ribityl lumazine and is converted from 5-amino-6-(5'-phosphoribosylamino)uracil via the enzyme 5-amino-6-(5-phosphoribosylamino)uracil reductase (EC 1.1.1.193). It is then converted into 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine via a hydrolase enzyme (EC 3.1.3.- ).
Structure
Data?1583854706
Synonyms
ValueSource
5-Amino-2,6-dioxy-4-(5'-phospho-D-ribitylamino)pyrimidineChEBI
5-Amino-2,6-dioxy-4-(5'-phosphoribitylamino)pyrimidineChEBI
5-Amino-6-(5'-phosphoribitylamino)uracilChEBI
5-Amino-6-(5-phosphoribitylamino)uracilChEBI
5-Amino-6-(5-phospho-D-ribitylamino)uracilKegg
5-Amino-2,6-dioxy-4-(5’-phospho-D-ribitylamino)pyrimidineHMDB
5-Amino-6-(5'-phospho-D-ribitylamino)uracilHMDB
5-Amino-6-(5’-phospho-D-ribitylamino)uracilHMDB
5-Amino-6-(5’-phosphoribitylamino)uracilHMDB
5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione-5'-phosphateHMDB
5-Amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione-5’-phosphateHMDB
Chemical FormulaC9H17N4O9P
Average Molecular Weight356.2264
Monoisotopic Molecular Weight356.073314674
IUPAC Name{[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxy}phosphonic acid
Traditional Name[(2R,3S,4S)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-2,3,4-trihydroxypentyl]oxyphosphonic acid
CAS Registry Number71491-01-5
SMILES
NC1=C(NC[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C9H17N4O9P/c10-5-7(12-9(18)13-8(5)17)11-1-3(14)6(16)4(15)2-22-23(19,20)21/h3-4,6,14-16H,1-2,10H2,(H2,19,20,21)(H3,11,12,13,17,18)/t3-,4+,6-/m0/s1
InChI KeyRQRINYISXYAZKL-RPDRRWSUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Secondary amine
  • Primary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • 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 Solubility2.89 g/LALOGPS
logP-2.5ALOGPS
logP-4.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area223.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity82.36 m³·mol⁻¹ChemAxon
Polarizability30.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-7932000000-f99b2e65ef6ba20ea0f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0249000000-aad1afed0b055e36f1f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-2932000000-8ce6cdef86c0d6904216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9810000000-0889d500d98fdc446282Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-6926000000-99084eeb27c449bf8cafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9100000000-7df2c276c4edd1cadab5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c2c18ea089d342debbafSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023235
KNApSAcK IDNot Available
Chemspider ID18921533
KEGG Compound IDC04454
BioCyc IDCPD-1086
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18666812
PDB IDNot Available
ChEBI ID18247
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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