Adenosine 5'-monophosphoric acid and its monosodium and disodium salts
General Information
| Mainterm | Adenosine 5'-monophosphoric acid and its monosodium and disodium salts |
| FEMA Number | 4224 |
| CAS Reg.No.(or other ID) | 61-19-8 |
| Regnum |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6083 |
| IUPAC Name | [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate |
| 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 |
| InChI Key | UDMBCSSLTHHNCD-KQYNXXCUSA-N |
| Canonical SMILES | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O |
| Molecular Formula | C10H14N5O7P |
| Wikipedia | adenosine phosphate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 347.224 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 4 |
| Complexity | 481.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B z u A I A A A A A A A A A A A A A A A A A A W J A A A A s A A A A A A A A A F g B + A A A H g A Q C C A A C B z h l w Y F 8 L 9 M F x C g Q Q Z h Z I C A g C 0 R E K A B U C A o V B C D W A J A y E A e R A g P A A L T A C D w M A I A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 186.0 |
| Monoisotopic Mass | 347.063 |
| Exact Mass | 347.063 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9402 |
| Human Intestinal Absorption | HIA- | 0.6115 |
| Caco-2 Permeability | Caco2- | 0.7398 |
| P-glycoprotein Substrate | Non-substrate | 0.6874 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9111 |
| Non-inhibitor | 0.9852 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9470 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4045 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8480 |
| CYP450 2D6 Substrate | Non-substrate | 0.8331 |
| CYP450 3A4 Substrate | Non-substrate | 0.5462 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9078 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9419 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9210 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9293 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9296 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9633 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9760 |
| Non-inhibitor | 0.8625 | |
| AMES Toxicity | Non AMES toxic | 0.8718 |
| Carcinogens | Non-carcinogens | 0.9239 |
| Fish Toxicity | Low FHMT | 0.6987 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8976 |
| Honey Bee Toxicity | Low HBT | 0.6660 |
| Biodegradation | Not ready biodegradable | 0.9793 |
| Acute Oral Toxicity | III | 0.4907 |
| Carcinogenicity (Three-class) | Non-required | 0.5557 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7041 | LogS |
| Caco-2 Permeability | -0.7556 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0220 | LD50, mol/kg |
| Fish Toxicity | 1.5457 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3744 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | Purine nucleotides |
| Subclass | Purine ribonucleotides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Purine ribonucleoside monophosphates |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Purine ribonucleoside monophosphate - Pentose phosphate - Pentose-5-phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Monosaccharide phosphate - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Monoalkyl phosphate - Alkyl phosphate - Monosaccharide - Pyrimidine - Imidolactam - N-substituted imidazole - Organic phosphoric acid derivative - Phosphoric acid ester - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - 1,2-diol - Organoheterocyclic compound - Oxacycle - Azacycle - Organonitrogen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Alcohol - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Amine - Aromatic heteropolycyclic compound |
| 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. |
From ClassyFire
Targets
- 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. Transcription activation is enhanced by the TORC coactivators which act independently of Ser-133 phosphorylation. Involved in different cellular processes including the synchronization of circadian rhythmicity and the differentiation of adipose cells.
- Gene Name:
- CREB1
- Uniprot ID:
- P16220
- Molecular Weight:
- 36687.86 Da
- General Function:
- Transcription factor binding
- Specific Function:
- Proto-oncogene with serine/threonine kinase activity involved in cell survival and cell proliferation and thus providing a selective advantage in tumorigenesis. Exerts its oncogenic activity through: the regulation of MYC transcriptional activity, the regulation of cell cycle progression and by phosphorylation and inhibition of proapoptotic proteins (BAD, MAP3K5, FOXO3). Phosphorylation of MYC leads to an increase of MYC protein stability and thereby an increase of transcriptional activity. The stabilization of MYC exerted by PIM1 might explain partly the strong synergism between these two oncogenes in tumorigenesis. Mediates survival signaling through phosphorylation of BAD, which induces release of the anti-apoptotic protein Bcl-X(L)/BCL2L1. Phosphorylation of MAP3K5, an other proapoptotic protein, by PIM1, significantly decreases MAP3K5 kinase activity and inhibits MAP3K5-mediated phosphorylation of JNK and JNK/p38MAPK subsequently reducing caspase-3 activation and cell apoptosis. Stimulates cell cycle progression at the G1-S and G2-M transitions by phosphorylation of CDC25A and CDC25C. Phosphorylation of CDKN1A, a regulator of cell cycle progression at G1, results in the relocation of CDKN1A to the cytoplasm and enhanced CDKN1A protein stability. Promote cell cycle progression and tumorigenesis by down-regulating expression of a regulator of cell cycle progression, CDKN1B, at both transcriptional and post-translational levels. Phosphorylation of CDKN1B,induces 14-3-3-proteins binding, nuclear export and proteasome-dependent degradation. May affect the structure or silencing of chromatin by phosphorylating HP1 gamma/CBX3. Acts also as a regulator of homing and migration of bone marrow cells involving functional interaction with the CXCL12-CXCR4 signaling axis.
- Gene Name:
- PIM1
- Uniprot ID:
- P11309
- Molecular Weight:
- 45411.905 Da
- 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 from antidepressants to antiasthmatic and anti-inflammatory agents.
- Gene Name:
- PDE4B
- Uniprot ID:
- Q07343
- Molecular Weight:
- 83342.695 Da
- 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 phosphorylases share catalytic and structural properties.
- Gene Name:
- PYGL
- Uniprot ID:
- P06737
- Molecular Weight:
- 97147.82 Da
- 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 intracellular ATP levels, AMPK activates energy-producing pathways and inhibits energy-consuming processes: inhibits protein, carbohydrate and lipid biosynthesis, as well as cell growth and proliferation. AMPK acts via direct phosphorylation of metabolic enzymes, and by longer-term effects via phosphorylation of transcription regulators. Also acts as a regulator of cellular polarity by remodeling the actin cytoskeleton; probably by indirectly activating myosin. Beta non-catalytic subunit acts as a scaffold on which the AMPK complex assembles, via its C-terminus that bridges alpha (PRKAA1 or PRKAA2) and gamma subunits (PRKAG1, PRKAG2 or PRKAG3).
- Gene Name:
- PRKAB1
- Uniprot ID:
- Q9Y478
- Molecular Weight:
- 30382.085 Da
- 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 guanosine 5'monophosphomorpholidate (GMP-morpholidate). Hydrolyzes lysyl-AMP (AMP-N-epsilon-(N-alpha-acetyl lysine methyl ester)) generated by lysine tRNA ligase, as well as Met-AMP, His-AMP and Asp-AMP, lysyl-GMP (GMP-N-epsilon-(N-alpha-acetyl lysine methyl ester)) and AMP-N-alanine methyl ester. Can also convert adenosine 5'-O-phosphorothioate and guanosine 5'-O-phosphorothioate to the corresponding nucleoside 5'-O-phosphates with concomitant release of hydrogen sulfide. In addition, functions as scaffolding protein that modulates transcriptional activation by the LEF1/TCF1-CTNNB1 complex and by the complex formed with MITF and CTNNB1. Modulates p53/TP53 levels and p53/TP53-mediated apoptosis. Modulates proteasomal degradation of target proteins by the SCF (SKP2-CUL1-F-box protein) E3 ubiquitin-protein ligase complex.
- Gene Name:
- HINT1
- Uniprot ID:
- P49773
- Molecular Weight:
- 13801.815 Da
- 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
- Molecular Weight:
- 91114.1 Da
- General Function:
- Atp binding
- Specific Function:
- Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
- Gene Name:
- ACSS1
- Uniprot ID:
- Q9NUB1
- Molecular Weight:
- 74856.1 Da
- 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
- Molecular Weight:
- 78579.11 Da
- 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 ATP levels, AMPK activates energy-producing pathways and inhibits energy-consuming processes: inhibits protein, carbohydrate and lipid biosynthesis, as well as cell growth and proliferation. AMPK acts via direct phosphorylation of metabolic enzymes, and by longer-term effects via phosphorylation of transcription regulators. Also acts as a regulator of cellular polarity by remodeling the actin cytoskeleton; probably by indirectly activating myosin. Regulates lipid synthesis by phosphorylating and inactivating lipid metabolic enzymes such as ACACA, ACACB, GYS1, HMGCR and LIPE; regulates fatty acid and cholesterol synthesis by phosphorylating acetyl-CoA carboxylase (ACACA and ACACB) and hormone-sensitive lipase (LIPE) enzymes, respectively. Regulates insulin-signaling and glycolysis by phosphorylating IRS1, PFKFB2 and PFKFB3. AMPK stimulates glucose uptake in muscle by increasing the translocation of the glucose transporter SLC2A4/GLUT4 to the plasma membrane, possibly by mediating phosphorylation of TBC1D4/AS160. Regulates transcription and chromatin structure by phosphorylating transcription regulators involved in energy metabolism such as CRTC2/TORC2, FOXO3, histone H2B, HDAC5, MEF2C, MLXIPL/ChREBP, EP300, HNF4A, p53/TP53, SREBF1, SREBF2 and PPARGC1A. Acts as a key regulator of glucose homeostasis in liver by phosphorylating CRTC2/TORC2, leading to CRTC2/TORC2 sequestration in the cytoplasm. In response to stress, phosphorylates 'Ser-36' of histone H2B (H2BS36ph), leading to promote transcription. Acts as a key regulator of cell growth and proliferation by phosphorylating TSC2, RPTOR and ATG1/ULK1: in response to nutrient limitation, negatively regulates the mTORC1 complex by phosphorylating RPTOR component of the mTORC1 complex and by phosphorylating and activating TSC2. In response to nutrient limitation, promotes autophagy by phosphorylating and activating ATG1/ULK1. AMPK also acts as a regulator of circadian rhythm by mediating phosphorylation of CRY1, leading to destabilize it. May regulate the Wnt signaling pathway by phosphorylating CTNNB1, leading to stabilize it. Also has tau-protein kinase activity: in response to amyloid beta A4 protein (APP) exposure, activated by CAMKK2, leading to phosphorylation of MAPT/TAU; however the relevance of such data remains unclear in vivo. Also phosphorylates CFTR, EEF2K, KLC1, NOS3 and SLC12A1.
- Gene Name:
- PRKAA1
- Uniprot ID:
- Q13131
- Molecular Weight:
- 64008.64 Da
- General Function:
- Identical protein binding
- 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 intracellular ATP levels, AMPK activates energy-producing pathways and inhibits energy-consuming processes: inhibits protein, carbohydrate and lipid biosynthesis, as well as cell growth and proliferation. AMPK acts via direct phosphorylation of metabolic enzymes, and by longer-term effects via phosphorylation of transcription regulators. Also acts as a regulator of cellular polarity by remodeling the actin cytoskeleton; probably by indirectly activating myosin. Beta non-catalytic subunit acts as a scaffold on which the AMPK complex assembles, via its C-terminus that bridges alpha (PRKAA1 or PRKAA2) and gamma subunits (PRKAG1, PRKAG2 or PRKAG3).
- Gene Name:
- PRKAB2
- Uniprot ID:
- O43741
- Molecular Weight:
- 30301.985 Da
- 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 regulatory processes in the central nervous system. May play a role in memory and learning. Plays a role in the regulation of the circadian rhythm of daytime contrast sensitivity probably by modulating the rhythmic synthesis of cyclic AMP in the retina (By similarity).
- Gene Name:
- ADCY1
- Uniprot ID:
- Q08828
- Molecular Weight:
- 123438.85 Da
- 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
- Molecular Weight:
- 77942.685 Da
- 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 glucose sensing and insulin secretion of pancreatic beta-cells. Appears to modulate glycerol gluconeogenesis in liver. Important regulator of appetite and adiposity; increased expression of the protein in liver after nutrient excess increases circulating satiety hormones and reduces appetite-stimulating neuropeptides and thus seems to provide a feedback mechanism to limit weight gain.
- Gene Name:
- FBP1
- Uniprot ID:
- P09467
- Molecular Weight:
- 36842.145 Da
- 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 intracellular adenine nucleotides.
- Gene Name:
- ADK
- Uniprot ID:
- P55263
- Molecular Weight:
- 40545.075 Da
From T3DB