P. aeruginosa Metabolome Database: 5-Amino-6-(5'-phosphoribosylamino)uracil (PAMDB000947)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB000947

Identification

Name:

5-Amino-6-(5'-phosphoribosylamino)uracil

Description:

5-amino-6-(5'-phosphoribosylamino)uracil is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

5-amino-6-(5'-phosphoribosylamino)uracil
5-Amino-6-(5-phosphoribosylamino)uracil
5-Amino-6-(ribosylamino)-2,4-(1H,3H)-pyrimidinedione 5'-phosphate
5-amino-6-(ribosylamino)-2,4-(1H,3H)-Pyrimidinedione 5'-phosphoric acid
5A6-5'PRAU

Chemical Formula:

C₉H₁₅N₄O₉P

Average Molecular Weight:

354.2106

Monoisotopic Molecular Weight:

354.05766461

InChI Key:

LZEXYCAGPMYXLX-UMMCILCDSA-N

InChI:

InChI=1S/C9H15N4O9P/c10-3-6(12-9(17)13-7(3)16)11-8-5(15)4(14)2(22-8)1-21-23(18,19)20/h2,4-5,8,14-15H,1,10H2,(H2,18,19,20)(H3,11,12,13,16,17)/t2-,4-,5-,8-/m1/s1

CAS number:

Not Available

IUPAC Name:

{[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional IUPAC Name:

[(2R,3S,4R,5R)-5-[(5-amino-2,6-dioxo-1,3-dihydropyrimidin-4-yl)amino]-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid

SMILES:

NC1=C(N[C@@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)NC(=O)NC1=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Glycosyl compounds

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Monosaccharide phosphate
Hydroxypyrimidine
Monoalkyl phosphate
Secondary aliphatic/aromatic amine
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Primary aromatic amine
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Monosaccharide
Heteroaromatic compound
Oxolane
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosyl compound (CHEBI:18337 )
ribose monophosphate (CHEBI:18337 )
aminouracil (CHEBI:18337 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	3.64 mg/mL	ALOGPS
logP	-1.8	ALOGPS
logP	-5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.21	ChemAxon
pKa (Strongest Basic)	3.27	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	212.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.88 m³·mol^-1	ChemAxon
Polarizability	29.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Hydrogen ion + Water > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonium
5-Amino-6-(5'-phosphoribosylamino)uracil + Hydrogen ion + NADPH > 5-Amino-6-(5'-phosphoribitylamino)uracil + NADP
2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + Water + 2,5-diamino-6-hydroxy-4-(5-phospho-D-ribosylamino)pyrimidine <> 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia
Water + 2,5-Diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine > 5-Amino-6-(5'-phosphoribosylamino)uracil + Ammonia

Pathways:

Riboflavin metabolism pae00740

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-0914000000-bfd0154077cf7db50381	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-2900000000-d3488d63b0eee9406798	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-8900000000-a92cbdbfe038ca5bbe5d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fv-9607000000-5c4c690d1a011ac633e3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9000000000-328e8307ada72eb610e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-67b8e3d0ec6c70e5c24c	View in MoNA

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18337
HMDB ID	Not Available
Pubchem Compound ID	439462
Kegg ID	C01268
ChemSpider ID	388566
Wikipedia ID	Not Available
BioCyc ID	CPD-602
EcoCyc ID	CPD-602

5-Amino-6-(5'-phosphoribosylamino)uracil (PAMDB000947)

Structure for 5-Amino-6-(5'-phosphoribosylamino)uracil (PAMDB000947)