1-(5-phospho-β-D-ribosyl)-AMP (PAMDB110483)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110483
Identification
Name: 1-(5-phospho-β-D-ribosyl)-AMP
Description:An AMP-sugar in which the hydrogen at position 1 of AMP is substituted by a 5-phospho-β-D-ribosyl group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-(5-phosphoribosyl)-AMP
  • phosphoribosyl-AMP
  • 5-phosphoribosyl-AMP
  • N-(5-phospho-D-ribosyl)-AMP
  • N-(5'-phospho-D-ribosyl)-AMP
  • N1-(5-phospho-D-ribosyl)-AMP
Chemical Formula: C15H19N5O14P2
Average Molecular Weight: 555.29
Monoisotopic Molecular Weight: 559.0716734937
InChI Key: RTQMRTSPTLIIHM-KEOHHSTQSA-J
InChI: InChI=1S/C15H23N5O14P2/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(33-14)1-31-35(25,26)27)20(3-17-7)15-11(24)9(22)6(34-15)2-32-36(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H2,25,26,27)(H2,28,29,30)/p-4/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
CAS number: Not Available
IUPAC Name:1-(5-O-phosphono-β-D-ribofuranosyl)adenosine 5'-(dihydrogen phosphate)
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-{1-[(2S,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-iminopurin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
SMILES:C(C4(C(C(C(N3(C(C2(=C(N(C1(C(C(C(O1)COP([O-])(=O)[O-])O)O))C=N2)N=C3))=N))O4)O)O))OP([O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.38 mg/mLALOGPS
logP-2.2ALOGPS
logP-4.1ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
pKa (Strongest Basic)5.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area290.17 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity122.54 m3·mol-1ChemAxon
Polarizability47.36 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
  • superpathway of histidine, purine, and pyrimidine biosynthesisPRPP-PWY
  • L-histidine biosynthesisHISTSYN-PWY
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0429120000-beecfdf73867149bf776View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0925000000-e85297f1f3428f363382View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-0934000000-eac6a05d73b6fe7aa32cView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-7409080000-3d9f7213b5a73bff11b8View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9403000000-bb5b8f4886bc364f6d44View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8be6c4a98ba2bf3f6c1dView in MoNA
    References
    References: Not Available
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    ChEBI8166
    HMDBHMDB12276
    IAF126042711
    KEGGC02741
    PubChem25244977