Adenosine phosphate

Identification

Generic Name
Adenosine phosphate
DrugBank Accession Number
DB00131
Background

Adenosine phosphate, or adenylic acid, is an adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position. Adenosine phosphate was withdrawn by the FDA since it was considered neither safe nor effective for its intended uses as a vasodilator and an anti-inflammatory.1

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical, Withdrawn
Structure
Weight
Average: 347.2212
Monoisotopic: 347.063084339
Chemical Formula
C10H14N5O7P
Synonyms
  • 5'-Adenosine monophosphate
  • 5'-Adenylic acid
  • 5'-AMP
  • 5'-O-Phosphonoadenosine
  • Adenosine 5'-(dihydrogen phosphate)
  • Adenosine 5'-monophosphate
  • Adenosine 5'-phosphate
  • Adenosine monophosphate
  • Adenosine phosphate
  • Adenosine-5'-Monophosphate
  • Adenosine-5'-monophosphoric acid
  • Adenosine-5'P
  • Adenosini phosphas
  • Adenylate
  • Adenylic acid
  • Ado5'P
  • AMP
  • Fosfato de adenosina
  • PAdo
  • Phosphate d'adénosine
External IDs
  • NSC-20264

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

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Pharmacodynamics

Adenosine 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 is used as a dietary supplement to boost immune activity, and is also used as a substitute sweetener to aid in the maintenance of a low-calorie diet.

Mechanism of action

Nucleotides such as Adenosine-5'-Monophosphate affect a number of immune functions, including the reversal of malnutrition and starvation-induced immunosuppression, the enhancement of T-cell maturation and function, the enhancement of natural killer cell activity, the improvement of delayed cutaneous hypersensitivity, helping resistance to such infectious agents as Staphylococcus aureus and Candida albicans, and finally the modulation of T-cell responses toward type 1 CD4 helper lymphocytes or Th1 cells. Studies have shown that mice fed a nucleotide-free diet have both impaired humoral and cellular immune responses. The addition of dietary nucleotides normalizes both types of responses. RNA, a delivery form of nucleotides, and ribonucleotides were used in these studies. The mechanism of the immune-enhancing activity of nucleic acids/nucleotides is not clear.

TargetActionsOrganism
A5'-AMP-activated protein kinase
activator
Humans
UAdenosine kinase
product of
Humans
U5'-AMP-activated protein kinase subunit beta-1
activator
Humans
UAcetyl-coenzyme A synthetase, cytoplasmic
product of
Humans
U5'-AMP-activated protein kinase catalytic subunit alpha-1
activator
Humans
UAdenylate cyclase type 1
product of
Humans
ULong-chain-fatty-acid--CoA ligase 1
product of
Humans
UCyclic AMP-responsive element-binding protein 1
activator
Humans
UDNA
component of
Humans
UcAMP-specific 3',5'-cyclic phosphodiesterase 4B
product of
Humans
UGlycogen phosphorylase, liver form
activator
Humans
UHistidine triad nucleotide-binding protein 1
product of
Humans
UcAMP-specific 3',5'-cyclic phosphodiesterase 4D
product of
Humans
UFructose-1,6-bisphosphatase 1
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Carbamoyl Phosphate Synthetase DeficiencyDisease
Argininosuccinic AciduriaDisease
Glycine and Serine MetabolismMetabolic
Ammonia RecyclingMetabolic
Propanoate MetabolismMetabolic
Arginine and Proline MetabolismMetabolic
Selenoamino Acid MetabolismMetabolic
Pentose Phosphate PathwayMetabolic
Histidine MetabolismMetabolic
Purine MetabolismMetabolic
Fatty Acid MetabolismMetabolic
Pyruvate MetabolismMetabolic
Glutamate MetabolismMetabolic
Butyrate MetabolismMetabolic
Thiamine MetabolismMetabolic
Cystathionine beta-Synthase DeficiencyDisease
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
HistidinemiaDisease
Leigh SyndromeDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Pyruvate Dehydrogenase Complex DeficiencyDisease
Clarithromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)Disease
Hyperinsulinism-Hyperammonemia SyndromeDisease
Hyperprolinemia Type IIDisease
Hyperprolinemia Type IDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
My-B-Den

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Tetrahydrofurans
show 8 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosine 5'-phosphate, purine ribonucleoside 5'-monophosphate (CHEBI:16027) / Ribonucleotides (C00020)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
415SHH325A
CAS number
61-19-8
InChI Key
UDMBCSSLTHHNCD-KQYNXXCUSA-N
InChI
InChI=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)/t4-,6-,7-,10-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1

References

Synthesis Reference

Shigehiro Kataoka, Ayako Nasu, Nobuyuki Yamaji, Motohiko Kato, "Process for preparation of N.sup.6 -substituted 3',5'-cyclic adenosine monophosphate and salt thereof." U.S. Patent US4751293, issued July, 1984.

US4751293
General References
  1. FDA Briefing Document: Pharmacy Compounding Advisory Committee (PCAC) Meeting February 23-24, 2015 [Link]
Human Metabolome Database
HMDB0000045
KEGG Drug
D02769
KEGG Compound
C00020
PubChem Compound
6083
PubChem Substance
46507628
ChemSpider
5858
BindingDB
18137
RxNav
309
ChEBI
16027
ChEMBL
CHEMBL752
ZINC
ZINC000003860156
Therapeutic Targets Database
DAP001319
PharmGKB
PA164744376
PDBe Ligand
AMP
Wikipedia
Adenosine_monophosphate
PDB Entries
12as / 1aer / 1am0 / 1amu / 1ank / 1aw4 / 1c0a / 1cja / 1ct9 / 1del
show 872 more
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusNot AvailableAsthma1
1CompletedPreventionMigraine1
0CompletedBasic ScienceReceptor Blockade1
Not AvailableCompletedNot AvailableMigraine Without Aura2
Not AvailableCompletedOtherHeadache / Migraine / Pain1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Spectrum Pharmaceuticals
Dosage Forms
Not Available
Prices
Unit descriptionCostUnit
Adenosine-5 monophosphate19.74USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195 dec °CPhysProp
water solubility1E+004 mg/L (at 20 °C)BEILSTEIN
logP-3.1Not Available
Predicted Properties
PropertyValueSource
logP-4.7Chemaxon
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)3.92Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area186.07 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity74.07 m3·mol-1Chemaxon
Polarizability29.96 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6115
Blood Brain Barrier+0.9402
Caco-2 permeable-0.7398
P-glycoprotein substrateNon-substrate0.6874
P-glycoprotein inhibitor INon-inhibitor0.9111
P-glycoprotein inhibitor IINon-inhibitor0.9852
Renal organic cation transporterNon-inhibitor0.947
CYP450 2C9 substrateNon-substrate0.848
CYP450 2D6 substrateNon-substrate0.8331
CYP450 3A4 substrateNon-substrate0.5462
CYP450 1A2 substrateNon-inhibitor0.9078
CYP450 2C9 inhibitorNon-inhibitor0.9419
CYP450 2D6 inhibitorNon-inhibitor0.921
CYP450 2C19 inhibitorNon-inhibitor0.9293
CYP450 3A4 inhibitorNon-inhibitor0.9296
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9633
Ames testNon AMES toxic0.8718
CarcinogenicityNon-carcinogens0.9239
BiodegradationNot ready biodegradable0.9793
Rat acute toxicity2.0220 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.976
hERG inhibition (predictor II)Non-inhibitor0.8625
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-014i-0974000000-7ce25c09f93913b81e9b
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-014i-0975000000-8175538459abaf92d36f
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002b-9713000000-019182f931e395f479cd
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0974000000-7ce25c09f93913b81e9b
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-0975000000-8175538459abaf92d36f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-052b-0209001000-f6c3cf706bb3b839d180
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-053s-0395300000-e2a342872025e6e960ae
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-2b9fb262817de641a5cd
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-053r-0007920000-ee7bab39079e225a1b07
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0109000000-52331e416cbdd8218b97
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-3900000000-ddc799b6e2bb5d5ac9a6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-68d6660e0cfbfb8f02ad
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-27f73c3a0a9566986a0e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03dm-0007009001-639c5cafae90b10dfc5f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0290000000-e0b5612abd24736e70da
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0039210000-3e5b716531d739ca25d9
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0009000000-9232b7438abb1f6256b6
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0007-2109007000-3e1cf347bd9e054b9368
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0006-0002009000-b840e6edcca65562937b
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-03di-0190000000-948ec97ae442eda212cb
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0002-0009000000-bd1c10704f289141803a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0109000000-433eab5bd833cd92f290
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-000b-0709000000-fa268a51905a453bc6f5
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-002b-9104000000-bc358c1d8c03290fc49d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0190000000-e0b5612abd24736e70da
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0009000000-9232b7438abb1f6256b6
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0002009000-b840e6edcca65562937b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-03di-0190000000-948ec97ae442eda212cb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0009000000-bd1c10704f289141803a
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-002b-9104000000-bc358c1d8c03290fc49d
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0191000000-d9199ecd902464f938c9
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-0191000000-2ceb9650f90db9780d24
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-2b9fb262817de641a5cd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-3900000000-ddc799b6e2bb5d5ac9a6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-68d6660e0cfbfb8f02ad
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-27f73c3a0a9566986a0e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0109000000-433eab5bd833cd92f290
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000b-0709000000-fa268a51905a453bc6f5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0pi9-0590000000-3baaa42fd9c5823f3d11
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0pi9-0590000000-e7a9a8c6e3397d3a6e43
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0009000000-49e398d18a8aa46a5d8f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0009000000-af1c8273b3b90933304e
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0942000000-86748fcec37a40624910
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0932000000-27a1df5cc0749ca01560
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-0059000000-dc0da0146a6e847d7650
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-7009000000-bd488cc1a020bb4a6fc2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920000000-2af3b532d1526c53a6a5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9001000000-3d9ca8c32aed5127c2d2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-066a3d8280dc3f873098
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-8901000000-0a43d94d114c8c0e7529
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6t-0059000000-dc0da0146a6e847d7650
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-7009000000-bd488cc1a020bb4a6fc2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9001000000-3d9ca8c32aed5127c2d2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920000000-2af3b532d1526c53a6a5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-066a3d8280dc3f873098
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-8901000000-0a43d94d114c8c0e7529
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.4277586
predicted
DarkChem Lite v0.1.0
[M-H]-183.8340586
predicted
DarkChem Lite v0.1.0
[M-H]-189.3852586
predicted
DarkChem Lite v0.1.0
[M-H]-187.7681586
predicted
DarkChem Lite v0.1.0
[M-H]-169.3063
predicted
DeepCCS 1.0 (2019)
[M-H]-188.4277586
predicted
DarkChem Lite v0.1.0
[M-H]-183.8340586
predicted
DarkChem Lite v0.1.0
[M-H]-189.3852586
predicted
DarkChem Lite v0.1.0
[M-H]-187.7681586
predicted
DarkChem Lite v0.1.0
[M-H]-188.4277586
predicted
DarkChem Lite v0.1.0
[M-H]-183.8340586
predicted
DarkChem Lite v0.1.0
[M-H]-189.3852586
predicted
DarkChem Lite v0.1.0
[M-H]-187.7681586
predicted
DarkChem Lite v0.1.0
[M-H]-169.3063
predicted
DeepCCS 1.0 (2019)
[M-H]-169.3063
predicted
DeepCCS 1.0 (2019)
[M+H]+188.4433586
predicted
DarkChem Lite v0.1.0
[M+H]+184.4388586
predicted
DarkChem Lite v0.1.0
[M+H]+188.1702586
predicted
DarkChem Lite v0.1.0
[M+H]+189.2912586
predicted
DarkChem Lite v0.1.0
[M+H]+171.70187
predicted
DeepCCS 1.0 (2019)
[M+H]+188.4433586
predicted
DarkChem Lite v0.1.0
[M+H]+184.4388586
predicted
DarkChem Lite v0.1.0
[M+H]+188.1702586
predicted
DarkChem Lite v0.1.0
[M+H]+189.2912586
predicted
DarkChem Lite v0.1.0
[M+H]+188.4433586
predicted
DarkChem Lite v0.1.0
[M+H]+184.4388586
predicted
DarkChem Lite v0.1.0
[M+H]+188.1702586
predicted
DarkChem Lite v0.1.0
[M+H]+189.2912586
predicted
DarkChem Lite v0.1.0
[M+H]+171.70187
predicted
DeepCCS 1.0 (2019)
[M+H]+171.70187
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.8845586
predicted
DarkChem Lite v0.1.0
[M+Na]+184.4345586
predicted
DarkChem Lite v0.1.0
[M+Na]+187.7342586
predicted
DarkChem Lite v0.1.0
[M+Na]+189.3767586
predicted
DarkChem Lite v0.1.0
[M+Na]+177.7541
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.8845586
predicted
DarkChem Lite v0.1.0
[M+Na]+184.4345586
predicted
DarkChem Lite v0.1.0
[M+Na]+187.7342586
predicted
DarkChem Lite v0.1.0
[M+Na]+189.3767586
predicted
DarkChem Lite v0.1.0
[M+Na]+187.8845586
predicted
DarkChem Lite v0.1.0
[M+Na]+184.4345586
predicted
DarkChem Lite v0.1.0
[M+Na]+187.7342586
predicted
DarkChem Lite v0.1.0
[M+Na]+189.3767586
predicted
DarkChem Lite v0.1.0
[M+Na]+177.7541
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.7541
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Activator
Curator comments
Adenosine phosphate activates AMPK.
General Function
Tau-protein kinase activity
Specific Function
Catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellular A...

Components:
References
  1. Marin-Aguilar F, Pavillard LE, Giampieri F, Bullon P, Cordero MD: Adenosine Monophosphate (AMP)-Activated Protein Kinase: A New Target for Nutraceutical Compounds. Int J Mol Sci. 2017 Jan 29;18(2). pii: ijms18020288. doi: 10.3390/ijms18020288. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Poly(a) rna binding
Specific Function
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
Gene Name
ADK
Uniprot ID
P55263
Uniprot Name
Adenosine kinase
Molecular Weight
40545.075 Da
References
  1. Park J, Gupta RS: Adenosine kinase and ribokinase--the RK family of proteins. Cell Mol Life Sci. 2008 Sep;65(18):2875-96. doi: 10.1007/s00018-008-8123-1. [Article]
  2. Leoncini R, Vannoni D, Santoro A, Giglioni S, Carli R, Marinello E: Adenosine kinase from rat liver: new biochemical properties. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):1107-12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Protein kinase activity
Specific Function
Non-catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellul...
Gene Name
PRKAB1
Uniprot ID
Q9Y478
Uniprot Name
5'-AMP-activated protein kinase subunit beta-1
Molecular Weight
30382.085 Da
References
  1. Richter EA, Kiens B, Wojtaszewski JF: [5'-adenosine monophosphate-activated protein kinase and lifestyle-mediated diseases]. Ugeskr Laeger. 2006 Feb 27;168(9):896-900. [Article]
  2. Neurath KM, Keough MP, Mikkelsen T, Claffey KP: AMP-dependent protein kinase alpha 2 isoform promotes hypoxia-induced VEGF expression in human glioblastoma. Glia. 2006 May;53(7):733-43. [Article]
  3. McGee SL, Hargreaves M: Exercise and skeletal muscle glucose transporter 4 expression: molecular mechanisms. Clin Exp Pharmacol Physiol. 2006 Apr;33(4):395-9. [Article]
  4. Whitehead JP, Richards AA, Hickman IJ, Macdonald GA, Prins JB: Adiponectin--a key adipokine in the metabolic syndrome. Diabetes Obes Metab. 2006 May;8(3):264-80. [Article]
  5. Ruderman NB, Saha AK: Metabolic syndrome: adenosine monophosphate-activated protein kinase and malonyl coenzyme A. Obesity (Silver Spring). 2006 Feb;14 Suppl 1:25S-33S. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Atp binding
Specific Function
Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name
ACSS2
Uniprot ID
Q9NR19
Uniprot Name
Acetyl-coenzyme A synthetase, cytoplasmic
Molecular Weight
78579.11 Da
References
  1. Ingram-Smith C, Smith KS: AMP-forming acetyl-CoA synthetases in Archaea show unexpected diversity in substrate utilization. Archaea. 2007 May;2(2):95-107. [Article]
  2. Linne U, Schafer A, Stubbs MT, Marahiel MA: Aminoacyl-coenzyme A synthesis catalyzed by adenylation domains. FEBS Lett. 2007 Mar 6;581(5):905-10. Epub 2007 Feb 7. [Article]
  3. Ingram-Smith C, Woods BI, Smith KS: Characterization of the acyl substrate binding pocket of acetyl-CoA synthetase. Biochemistry. 2006 Sep 26;45(38):11482-90. [Article]
  4. Reger AS, Carney JM, Gulick AM: Biochemical and crystallographic analysis of substrate binding and conformational changes in acetyl-CoA synthetase. Biochemistry. 2007 Jun 5;46(22):6536-46. Epub 2007 May 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Tau-protein kinase activity
Specific Function
Catalytic subunit of AMP-activated protein kinase (AMPK), an energy sensor protein kinase that plays a key role in regulating cellular energy metabolism. In response to reduction of intracellular A...
Gene Name
PRKAA1
Uniprot ID
Q13131
Uniprot Name
5'-AMP-activated protein kinase catalytic subunit alpha-1
Molecular Weight
64008.64 Da
References
  1. Mayes MA, Laforest MF, Guillemette C, Gilchrist RB, Richard FJ: Adenosine 5'-monophosphate kinase-activated protein kinase (PRKA) activators delay meiotic resumption in porcine oocytes. Biol Reprod. 2007 Apr;76(4):589-97. Epub 2006 Dec 13. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Metal ion binding
Specific Function
Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling. Mediates responses to increased cellular Ca(2+)/calmodulin levels (By similarity). May be involved in regu...
Gene Name
ADCY1
Uniprot ID
Q08828
Uniprot Name
Adenylate cyclase type 1
Molecular Weight
123438.85 Da
References
  1. Yang ZF, Sun Y, Li CZ, Wang HW, Wang XJ, Zheng YQ, Liu K, Liu YM: Reduced sinoatrial cAMP content plays a role in postnatal heart rate slowing in the rabbit. Clin Exp Pharmacol Physiol. 2006 Aug;33(8):757-62. [Article]
  2. Nicol X, Bennis M, Ishikawa Y, Chan GC, Reperant J, Storm DR, Gaspar P: Role of the calcium modulated cyclases in the development of the retinal projections. Eur J Neurosci. 2006 Dec;24(12):3401-14. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Long-chain fatty acid-coa ligase activity
Specific Function
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses palmitoleate, oleate and linoleate.
Gene Name
ACSL1
Uniprot ID
P33121
Uniprot Name
Long-chain-fatty-acid--CoA ligase 1
Molecular Weight
77942.685 Da
References
  1. Ingram-Smith C, Woods BI, Smith KS: Characterization of the acyl substrate binding pocket of acetyl-CoA synthetase. Biochemistry. 2006 Sep 26;45(38):11482-90. [Article]
  2. Ingram-Smith C, Smith KS: AMP-forming acetyl-CoA synthetases in Archaea show unexpected diversity in substrate utilization. Archaea. 2007 May;2(2):95-107. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Transcriptional activator activity, rna polymerase ii transcription factor binding
Specific Function
Phosphorylation-dependent transcription factor that stimulates transcription upon binding to the DNA cAMP response element (CRE), a sequence present in many viral and cellular promoters. Transcript...
Gene Name
CREB1
Uniprot ID
P16220
Uniprot Name
Cyclic AMP-responsive element-binding protein 1
Molecular Weight
36687.86 Da
References
  1. Ulfhammer E, Larsson P, Karlsson L, Hrafnkelsdottir T, Bokarewa M, Tarkowski A, Jern S: TNF-alpha mediated suppression of tissue type plasminogen activator expression in vascular endothelial cells is NF-kappaB- and p38 MAPK-dependent. J Thromb Haemost. 2006 Aug;4(8):1781-9. [Article]
  2. Saha B, Singh SK, Sarkar C, Bera R, Ratha J, Tobin DJ, Bhadra R: Activation of the Mitf promoter by lipid-stimulated activation of p38-stress signalling to CREB. Pigment Cell Res. 2006 Dec;19(6):595-605. [Article]
  3. Kozinn J, Mao L, Arora A, Yang L, Fibuch EE, Wang JQ: Inhibition of glutamatergic activation of extracellular signal-regulated protein kinases in hippocampal neurons by the intravenous anesthetic propofol. Anesthesiology. 2006 Dec;105(6):1182-91. [Article]
  4. Perlis RH, Purcell S, Fagerness J, Cusin C, Yamaki L, Fava M, Smoller JW: Clinical and genetic dissection of anger expression and CREB1 polymorphisms in major depressive disorder. Biol Psychiatry. 2007 Sep 1;62(5):536-40. Epub 2007 Feb 14. [Article]
  5. Brenhouse HC, Howe ML, Stellar JR: Differential activation of cAMP response element binding protein in discrete nucleus accumbens subregions during early and late cocaine sensitization. Behav Neurosci. 2007 Feb;121(1):212-7. [Article]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
Actions
Component of
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Kostylina G, Simon D, Fey MF, Yousefi S, Simon HU: Neutrophil apoptosis mediated by nicotinic acid receptors (GPR109A). Cell Death Differ. 2008 Jan;15(1):134-42. Epub 2007 Oct 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight
83342.695 Da
References
  1. Siuciak JA, Chapin DS, McCarthy SA, Martin AN: Antipsychotic profile of rolipram: efficacy in rats and reduced sensitivity in mice deficient in the phosphodiesterase-4B (PDE4B) enzyme. Psychopharmacology (Berl). 2007 Jun;192(3):415-24. Epub 2007 Mar 2. [Article]
  2. Porteous DJ, Thomson P, Brandon NJ, Millar JK: The genetics and biology of DISC1--an emerging role in psychosis and cognition. Biol Psychiatry. 2006 Jul 15;60(2):123-31. [Article]
  3. Terrin A, Di Benedetto G, Pertegato V, Cheung YF, Baillie G, Lynch MJ, Elvassore N, Prinz A, Herberg FW, Houslay MD, Zaccolo M: PGE(1) stimulation of HEK293 cells generates multiple contiguous domains with different [cAMP]: role of compartmentalized phosphodiesterases. J Cell Biol. 2006 Nov 6;175(3):441-51. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
Curator comments
Evidence was found in rabbits and the relevance to humans is unknown.
General Function
Vitamin binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGL
Uniprot ID
P06737
Uniprot Name
Glycogen phosphorylase, liver form
Molecular Weight
97147.82 Da
References
  1. Oikonomakos NG, Kosmopoulou MN, Chrysina ED, Leonidas DD, Kostas ID, Wendt KU, Klabunde T, Defossa E: Crystallographic studies on acyl ureas, a new class of glycogen phosphorylase inhibitors, as potential antidiabetic drugs. Protein Sci. 2005 Jul;14(7):1760-71. doi: 10.1110/ps.051432405. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Protein kinase c binding
Specific Function
Hydrolyzes purine nucleotide phosphoramidates with a single phosphate group, including adenosine 5'monophosphoramidate (AMP-NH2), adenosine 5'monophosphomorpholidate (AMP-morpholidate) and guanosin...
Gene Name
HINT1
Uniprot ID
P49773
Uniprot Name
Histidine triad nucleotide-binding protein 1
Molecular Weight
13801.815 Da
References
  1. Chou TF, Tikh IB, Horta BA, Ghosh B, De Alencastro RB, Wagner CR: Engineered monomeric human histidine triad nucleotide-binding protein 1 hydrolyzes fluorogenic acyl-adenylate and lysyl-tRNA synthetase-generated lysyl-adenylate. J Biol Chem. 2007 May 18;282(20):15137-47. Epub 2007 Mar 2. [Article]
  2. Chou TF, Wagner CR: Lysyl-tRNA synthetase-generated lysyl-adenylate is a substrate for histidine triad nucleotide binding proteins. J Biol Chem. 2007 Feb 16;282(7):4719-27. Epub 2006 Dec 8. [Article]
  3. Chou TF, Baraniak J, Kaczmarek R, Zhou X, Cheng J, Ghosh B, Wagner CR: Phosphoramidate pronucleotides: a comparison of the phosphoramidase substrate specificity of human and Escherichia coli histidine triad nucleotide binding proteins. Mol Pharm. 2007 Mar-Apr;4(2):208-17. Epub 2007 Jan 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Product of
General Function
Ubiquitin protein ligase binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name
PDE4D
Uniprot ID
Q08499
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Molecular Weight
91114.1 Da
References
  1. Terrin A, Di Benedetto G, Pertegato V, Cheung YF, Baillie G, Lynch MJ, Elvassore N, Prinz A, Herberg FW, Houslay MD, Zaccolo M: PGE(1) stimulation of HEK293 cells generates multiple contiguous domains with different [cAMP]: role of compartmentalized phosphodiesterases. J Cell Biol. 2006 Nov 6;175(3):441-51. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Inhibitory allosteric modulator
General Function
Monosaccharide binding
Specific Function
Catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate in the presence of divalent cations, acting as a rate-limiting enzyme in gluconeogenesis. Plays a role in regulating gl...
Gene Name
FBP1
Uniprot ID
P09467
Uniprot Name
Fructose-1,6-bisphosphatase 1
Molecular Weight
36842.145 Da
References
  1. Xue Y, Huang S, Liang JY, Zhang Y, Lipscomb WN: Crystal structure of fructose-1,6-bisphosphatase complexed with fructose 2,6-bisphosphate, AMP, and Zn2+ at 2.0-A resolution: aspects of synergism between inhibitors. Proc Natl Acad Sci U S A. 1994 Dec 20;91(26):12482-6. [Article]
  2. Hebeisen P, Kuhn B, Kohler P, Gubler M, Huber W, Kitas E, Schott B, Benz J, Joseph C, Ruf A: Allosteric FBPase inhibitors gain 10(5) times in potency when simultaneously binding two neighboring AMP sites. Bioorg Med Chem Lett. 2008 Aug 15;18(16):4708-12. doi: 10.1016/j.bmcl.2008.06.103. Epub 2008 Jul 5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Metal ion binding
Specific Function
AMP deaminase plays a critical role in energy metabolism.
Gene Name
AMPD1
Uniprot ID
P23109
Uniprot Name
AMP deaminase 1
Molecular Weight
90218.455 Da
References
  1. Hanisch F, Hellsten Y, Zierz S: Ecto- and cytosolic 5'-nucleotidases in normal and AMP deaminase-deficient human skeletal muscle. Biol Chem. 2006 Jan;387(1):53-8. [Article]
  2. Palecz D, Jaszczuk E, Gabryelak T: In vitro study of AMP-deaminase from fish (Cyprinus carpio) treated with hydrolyzable tannins. Acta Biol Hung. 2006 Mar;57(1):49-56. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Amp binding
Specific Function
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name
APRT
Uniprot ID
P07741
Uniprot Name
Adenine phosphoribosyltransferase
Molecular Weight
19607.535 Da
References
  1. Barrett C, Alley J, Pulido JC, Spurling H, Li P, Parsons T, Mallender WD, Bembenek ME: Configuration of a scintillation proximity assay for the activity assessment of recombinant human adenine phosphoribosyltransferase. Assay Drug Dev Technol. 2006 Dec;4(6):661-9. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42