Record Information
Version1.0
Creation date2011-04-11 17:01:39 UTC
Update date2015-10-09 22:29:20 UTC
Primary IDFDB021806
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAdenosine monophosphate
DescriptionAdenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable [HMDB]
CAS Number61-19-8
Structure
Thumb
Synonyms
SynonymSource
5'-Adenosine monoateChEBI
5'-Adenosine monoic acidGenerator
5'-AdenylateGenerator
5'-Adenylic acidChEBI
5'-AMPChEBI
5'-O-OnoadenosineChEBI
AdenHMDB
Adenosine 5'-(dihydrogen ate)ChEBI
Adenosine 5'-(dihydrogen ic acid)Generator
Adenosine 5'-ateChEBI
Adenosine 5'-ic acidGenerator
Adenosine 5'-monoateChEBI
Adenosine 5'-monoic acidGenerator
Adenosine 5'-orateHMDB
Adenosine 5'-oric acidHMDB
Adenosine ateChEBI
Adenosine ic acidGenerator
ADENOSINE monoATEChEBI
ADENOSINE monoic acidGenerator
Adenosine-5-monoorateHMDB
Adenosine-5-monooric acidHMDB
Adenosine-5'-monoateGenerator
Adenosine-5'-monoic acidGenerator
Adenosine-5'-monoorateHMDB
Adenosine-5'-monooric acidChEBI
Adenosine-5'pChEBI
Adenosine-ateHMDB
Adenosine-monoateHMDB
Adenosini asChEBI
AdenoviteHMDB
AdenylateChEBI
Adenylic acidChEBI
Ado5'pChEBI
ate D'adenosineChEBI
CardiomoneHMDB
EntasideHMDB
Fosfato de adenosinaChEBI
ic acid D'adenosineGenerator
LycedanHMDB
Muscle adenylateHMDB
Muscle adenylic acidHMDB
My-b-denHMDB
My-beta-denHMDB
PAdoChEBI
PhosadenHMDB
Predicted Properties
PropertyValueSource
Water Solubility3.31 g/LALOGPS
logP-3.1ALOGPS
logP-4.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area186.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.07 m³·mol⁻¹ChemAxon
Polarizability29.83 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14N5O7P
IUPAC name{[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)
InChI KeyInChIKey=UDMBCSSLTHHNCD-UHFFFAOYSA-N
Isomeric SMILESNC1=C2N=CN(C3OC(COP(O)(O)=O)C(O)C3O)C2=NC=N1
Average Molecular Weight347
Monoisotopic Molecular Weight347
Classification
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5858
ChEMBL IDCHEMBL752
KEGG Compound IDC00020
Pubchem Compound ID6083
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00131
HMDB IDHMDB00045
CRC / DFC (Dictionary of Food Compounds) IDHFV18-R:HFV18-R
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33534
KNApSAcK IDNot Available
HET IDA
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Tyrosine--tRNA ligase, cytoplasmicYARSP54577
Tyrosine--tRNA ligase, mitochondrialYARS2Q9Y2Z4
Valine--tRNA ligaseVARSP26640
Valine--tRNA ligase, mitochondrialVARS2Q5ST30
Lysine--tRNA ligaseKARSQ15046
Glycine--tRNA ligaseGARSP41250
Alanine--tRNA ligase, cytoplasmicAARSP49588
Alanine--tRNA ligase, mitochondrialAARS2Q5JTZ9
Bifunctional glutamate/proline--tRNA ligaseEPRSP07814
Probable proline--tRNA ligase, mitochondrialPARS2Q7L3T8
Serum paraoxonase/lactonase 3PON3Q15166
Asparagine synthetase [glutamine-hydrolyzing]ASNSP08243
Asparagine--tRNA ligase, cytoplasmicNARSO43776
Probable asparagine--tRNA ligase, mitochondrialNARS2Q96I59
Glycogen phosphorylase, liver formPYGLP06737
Glycogen phosphorylase, muscle formPYGMP11217
Glycogen phosphorylase, brain formPYGBP11216
Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaPDE6HQ13956
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BPDE1BQ01064
cGMP-inhibited 3',5'-cyclic phosphodiesterase BPDE3BQ13370
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaPDE6GP18545
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaPDE6DO43924
Probable leucine--tRNA ligase, mitochondrialLARS2Q15031
Leucine--tRNA ligase, cytoplasmicLARSQ9P2J5
Deoxycytidine kinaseDCKP27707
Tryptophan--tRNA ligase, cytoplasmicWARSP23381
Tryptophan--tRNA ligase, mitochondrialWARS2Q9UGM6
Arginine--tRNA ligase, cytoplasmicRARSP54136
Argininosuccinate synthaseASS1P00966
Probable arginine--tRNA ligase, mitochondrialRARS2Q5T160
Selenide, water dikinase 2SEPHS2Q99611
Adenylosuccinate lyaseADSLP30566
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
AMP deaminase 3AMPD3Q01432
AMP deaminase 2AMPD2Q01433
AMP deaminase 1AMPD1P23109
Adenine phosphoribosyltransferaseAPRTP07741
GTP:AMP phosphotransferase, mitochondrialAK3Q9UIJ7
Acetyl-coenzyme A synthetase, cytoplasmicACSS2Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrialACSS1Q9NUB1
Thiamin pyrophosphokinase 1TPK1Q9H3S4
Probable glutamate--tRNA ligase, mitochondrialEARS2Q5JPH6
Bifunctional ATP-dependent dihydroxyacetone kinase/FAD-AMP lyase (cyclizing)DAKQ3LXA3
Ubiquitin-conjugating enzyme E2 D2UBE2D2P62837
Long-chain-fatty-acid--CoA ligase ACSBG2ACSBG2Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1ACSBG1Q96GR2
Probable histidine--tRNA ligase, mitochondrialHARS2P49590
Histidine--tRNA ligase, cytoplasmicHARSP12081
Phosphopantothenate--cysteine ligasePPCSQ9HAB8
Threonine--tRNA ligase, cytoplasmicTARSP26639
Probable threonine--tRNA ligase 2, cytoplasmicTARSL2A2RTX5
Threonine--tRNA ligase, mitochondrialTARS2Q9BW92
Methionine--tRNA ligase, cytoplasmicMARSP56192
Methionine--tRNA ligase, mitochondrialMARS2Q96GW9
Glutamine--tRNA ligaseQARSP47897
Adenylate kinase 2, mitochondrialAK2P54819
Isoleucine--tRNA ligase, cytoplasmicIARSP41252
Isoleucine--tRNA ligase, mitochondrialIARS2Q9NSE4
Aspartate--tRNA ligase, cytoplasmicDARSP14868
Aspartate--tRNA ligase, mitochondrialDARS2Q6PI48
Cysteine--tRNA ligase, cytoplasmicCARSP49589
Serine--tRNA ligase, mitochondrialSARS2Q9NP81
Serine--tRNA ligase, cytoplasmicSARSP49591
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Phenylalanine--tRNA ligase, mitochondrialFARS2O95363
Biotin--protein ligaseHLCSP50747
Phenylalanine--tRNA ligase beta subunitFARSBQ9NSD9
Ubiquitin-conjugating enzyme E2 AUBE2AP49459
NEDD8-conjugating enzyme Ubc12UBE2MP61081
Ubiquitin/ISG15-conjugating enzyme E2 L6UBE2L6O14933
Ubiquitin-conjugating enzyme E2 G1UBE2G1P62253
Ubiquitin-conjugating enzyme E2 E2UBE2E2Q96LR5
DNA ligase 4LIG4P49917
Ubiquitin-conjugating enzyme E2 BUBE2BP63146
Ubiquitin-conjugating enzyme E2 J2UBE2J2Q8N2K1
Ubiquitin-conjugating enzyme E2 L3UBE2L3P68036
RNA 3'-terminal phosphate cyclaseRTCAO00442
Ubiquitin-conjugating enzyme E2 D3UBE2D3P61077
Ubiquitin-like modifier-activating enzyme 1UBA1P22314
Ubiquitin-conjugating enzyme E2 E1UBE2E1P51965
SUMO-conjugating enzyme UBC9UBE2IP63279
Ubiquitin-conjugating enzyme E2 J1UBE2J1Q9Y385
Ubiquitin-conjugating enzyme E2 CUBE2CO00762
Selenide, water dikinase 1SEPHS1P49903
Ubiquitin-conjugating enzyme E2 NUBE2NP61088
DNA ligase 1LIG1P18858
E3 ubiquitin-protein ligase NEDD4-likeNEDD4LQ96PU5
Acetoacetyl-CoA synthetaseAACSQ86V21
Acyl-CoA synthetase family member 4AASDHQ4L235
FARSLA proteinFARSLAQ6IBR2
SUMO-activating enzyme subunit 2UBA2Q9UBT2
E3 ubiquitin-protein ligase HUWE1HUWE1Q7Z6Z7
E3 ubiquitin-protein ligase ToporsTOPORSQ9NS56
STIP1 homology and U-box containing protein 1 (STIP1 homology and U- box containing protein 1, isoform CRA_c)STUB1Q9UNE7
Ubiquitin conjugation factor E4 BUBE4BO95155
Membrane-associated ring finger (C3HC4) 6 (Membrane-associated ring finger (C3HC4) 6, isoform CRA_a)MARCH6O60337
NEDD4-like E3 ubiquitin-protein ligase WWP2WWP2O00308
E3 ubiquitin-protein ligase MARCH3MARCH3Q86UD3
NEDD8-conjugating enzyme UBE2FUBE2FQ969M7
Ubiquitin-conjugating enzyme E2 UUBE2UQ5VVX9
Probable E3 ubiquitin-protein ligase MARCH10MARCH10Q8NA82
E3 ubiquitin-protein ligase UBR1UBR1Q8IWV7
E3 ubiquitin-protein ligase MARCH8MARCH8Q5T0T0
E3 ubiquitin-protein ligase ZNRF2ZNRF2Q8NHG8
E3 ubiquitin-protein ligase TRIM32TRIM32Q13049
Probable E3 ubiquitin-protein ligase MYCBP2MYCBP2O75592
E3 ubiquitin-protein ligase MGRN1MGRN1O60291
E3 ubiquitin-protein ligase UBR2UBR2Q8IWV8
E3 ubiquitin-protein ligase UBR4UBR4Q5T4S7
E3 ubiquitin-protein ligase AMFRAMFRQ9UKV5
Ubiquitin-conjugating enzyme E2 SUBE2SQ16763
Pre-mRNA-processing factor 19PRPF19Q9UMS4
Myosin regulatory light chain interacting protein (Myosin regulatory light chain interacting protein, isoform CRA_a)MYLIPQ8WY64
HNP95hNp95Q96T88
Putative ubiquitin-conjugating enzyme E2 N-likeUBE2NLQ5JXB2
Midline-1MID1O15344
E3 ubiquitin-protein ligase NEDD4NEDD4P46934
CCR4-NOT transcription complex subunit 4CNOT4O95628
E3 ubiquitin-protein ligase MARCH2MARCH2Q9P0N8
E3 ubiquitin-protein ligase UBR5UBR5O95071
E3 ubiquitin-protein ligase TRIM33TRIM33Q9UPN9
E3 ubiquitin-protein ligase MARCH5MARCH5Q9NX47
Ubiquitin-conjugating enzyme E2 R2UBE2R2Q712K3
E3 ubiquitin-protein ligase MARCH1MARCH1Q8TCQ1
E3 ubiquitin-protein ligase FANCLFANCLQ9NW38
Ubiquitin-like modifier-activating enzyme 6UBA6A0AVT1
Ubiquitin-conjugating enzyme E2 WUBE2WQ96B02
Galactosyl transferase-associated proteinGTAPQ29SN7
E3 ubiquitin-protein ligase CHFRCHFRQ96EP1
Ring finger protein 20RNF20Q5VTR2
E3 ubiquitin-protein ligase RAD18RAD18Q9NS91
E3 ubiquitin ligase SMURF1SMURF1Q9HCE7
Baculoviral IAP repeat-containing protein 6BIRC6Q9NR09
E3 ubiquitin-protein ligase MARCH4MARCH4Q9P2E8
E3 ubiquitin-protein ligase CCNB1IP1CCNB1IP1Q9NPC3
E3 ubiquitin-protein ligase RNF5RNF5Q99942
Ubiquitin-conjugating enzyme E2 OUBE2OQ9C0C9
Praja 1PJA1A2A322
RFWD2 proteinRFWD2Q05CT6
E3 ubiquitin-protein ligase SMURF2SMURF2Q9HAU4
E3 ubiquitin-protein ligase SIAH1SIAH1Q8IUQ4
E3 ubiquitin-protein ligase SIAH2SIAH2O43255
E3 ubiquitin-protein ligase MARCH7MARCH7Q9H992
Ubiquitin-conjugating enzyme E2 ZUBE2ZQ9H832
Ubiquitin-like modifier-activating enzyme 7UBA7P41226
Ubiquitin carrier proteinUBE2HA4D1L5
Ubiquitin-protein ligase E3AUBE3AQ05086
E3 ubiquitin-protein ligase RNF128RNF128Q8TEB7
E3 ubiquitin-protein ligase TRIM11TRIM11Q96F44
E3 ubiquitin-protein ligase synoviolinSYVN1Q86TM6
E3 ubiquitin-protein ligase TRIM63TRIM63Q969Q1
E3 ubiquitin-protein ligase LNXLNX1Q8TBB1
E3 ubiquitin-protein ligase ZNRF1ZNRF1Q8ND25
Tripartite motif-containing protein 5TRIM5Q9C035
Ubiquitin-protein ligase E3BUBE3BQ7Z3V4
E3 ubiquitin-protein ligase RNF8RNF8O76064
E3 ubiquitin-protein ligase LRSAM1LRSAM1Q6UWE0
Ubiquitin-conjugating enzyme E2 Q2UBE2Q2Q8WVN8
E3 ubiquitin-protein ligase MARCH9MARCH9Q86YJ5
Probable E3 ubiquitin-protein ligase TRIP12TRIP12Q14669
E3 ubiquitin-protein ligase DZIP3DZIP3Q86Y13
Ubiquitin-protein ligase E3CUBE3CQ15386
E3 ubiquitin-protein ligase MIB1MIB1Q86YT6
E3 ubiquitin-protein ligase RNF138RNF138Q8WVD3
E3 ubiquitin-protein ligase RING2RNF2Q99496
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPTQ9NRN7
SUMO-activating enzyme subunit 1SAE1Q9UBE0
Ubiquitin-conjugating enzyme E2 D4UBE2D4Q9Y2X8
Ubiquitin conjugation factor E4 AUBE4AQ14139
E3 ubiquitin-protein ligase RNF144BRNF144BQ7Z419
Phenylalanine--tRNA ligase alpha subunitFARSAQ9Y285
Adenylate kinase isoenzyme 1AK1P00568
Adenylate kinase isoenzyme 4, mitochondrialAK4P27144
Adenylate kinase 7AK7Q96M32
Very long-chain acyl-CoA synthetaseSLC27A2O14975
Adenylyltransferase and sulfurtransferase MOCS3MOCS3O95396
Lipoyltransferase 1, mitochondrialLIPT1Q9Y234
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Ethanol DegradationSMP00449 Not Available
Glycine and Serine MetabolismSMP00004 map00260
Histidine MetabolismSMP00044 map00340
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482 Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481 Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480 Not Available
Purine MetabolismSMP00050 map00230
Transcription/TranslationSMP00019 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference