Adenosine
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Basic Info
| Common Name | Adenosine(F05314) |
| 2D Structure | |
| Description | Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. |
| FRCD ID | F05314 |
| CAS Number | 58-61-7 |
| PubChem CID | 60961 |
| Formula | C10H13N5O4 |
| IUPAC Name | (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol |
| InChI Key | OIRDTQYFTABQOQ-KQYNXXCUSA-N |
| InChI | InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 |
| Canonical SMILES | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)O |
| Isomeric SMILES | C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O |
| Wikipedia | Adenosine |
| Synonyms |
adenosine
58-61-7
Adenocard
Adenoscan
Adenine riboside
Adenosin
beta-D-Adenosine
Nucleocardyl
Boniton
Sandesin
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | Purine nucleosides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Purine nucleosides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxygen compound - Organic nitrogen compound - Alcohol - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Amine - Primary alcohol - Primary amine - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 267.245 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 2 |
| Complexity | 335 |
| Monoisotopic Mass | 267.097 |
| Exact Mass | 267.097 |
| XLogP | -1.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| 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 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9383 |
| Human Intestinal Absorption | HIA+ | 0.9227 |
| Caco-2 Permeability | Caco2- | 0.8957 |
| P-glycoprotein Substrate | Non-substrate | 0.7026 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9660 |
| Non-inhibitor | 0.9533 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9444 |
| Distribution | ||
| Subcellular localization | Nucleus | 0.4394 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8639 |
| CYP450 2D6 Substrate | Non-substrate | 0.8349 |
| CYP450 3A4 Substrate | Non-substrate | 0.5866 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9667 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9595 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9770 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9514 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9620 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9701 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9890 |
| Non-inhibitor | 0.9102 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9182 |
| Fish Toxicity | Low FHMT | 0.9399 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5972 |
| Honey Bee Toxicity | Low HBT | 0.7946 |
| Biodegradation | Not ready biodegradable | 0.9738 |
| Acute Oral Toxicity | III | 0.7890 |
| Carcinogenicity (Three-class) | Non-required | 0.5680 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8368 | LogS |
| Caco-2 Permeability | -0.5569 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9715 | LD50, mol/kg |
| Fish Toxicity | 1.6619 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1711 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Mechanistic considerations in chemotherapeutic activity of caffeine. | Biomed Pharmacother | 2018 Sep | 29864619 |
| Fluorescent DNA Probing Nanoscale MnO2: Adsorption, Dissolution by Thiol, andNanozyme Activity. | Langmuir | 2018 Mar 6 | 29457975 |
| Cold atmospheric pressure plasma causes protein denaturation and endoplasmic reticulum stress in Saccharomyces cerevisiae. | Appl Microbiol Biotechnol | 2018 Mar | 29356871 |
| Linoleic Acid Attenuates the Toxic Dose of Bupivacaine-Mediated Reduction of Vasodilation Evoked by the Activation of Adenosine Triphosphate-Sensitive Potassium Channels. | Int J Mol Sci | 2018 Jun 26 | 29949899 |
| The Bacterial Protein CNF1 as a Potential Therapeutic Strategy against Mitochondrial Diseases: A Pilot Study. | Int J Mol Sci | 2018 Jun 21 | 29933571 |
| Mechanism of bisphenol AF-induced progesterone inhibition in human chorionic gonadotrophin-stimulated mouse Leydig tumor cell line (mLTC-1) cells. | Environ Toxicol | 2018 Jun | 29575470 |
| Cytotoxicity of 34 FDA approved small-molecule kinase inhibitors in primary rat and human hepatocytes. | Toxicol Lett | 2018 Jul | 29655783 |
| A novel, efficient, and ecologically relevant bioassay method using aquatic fungi and fungus-like organisms for fungicide ecological effect assessment. | Environ Toxicol Chem | 2018 Jul | 29572919 |
| Obesogenic diets alter metabolism in mice. | PLoS One | 2018 Jan 11 | 29324762 |
| Changes of adenosinergic system in piglets fed a diet co-contaminated by mycotoxin and their effects on the regulation of adenosine. | Microb Pathog | 2018 Jan | 29217327 |
| Comparison of Inhibitory Capacities of 6-, 8- and 10-Gingerols/Shogaols on the Canonical NLRP3 Inflammasome-Mediated IL-1β Secretion. | Molecules | 2018 Feb 21 | 29466287 |
| The adenosine A2A receptor agonist T1-11 ameliorates neurovisceral symptoms andextends the lifespan of a mouse model of Niemann-Pick type C disease. | Neurobiol Dis | 2018 Feb | 29079454 |
| Dietary enzymatically treated Artemisia annua L. improves meat quality,antioxidant capacity and energy status of breast muscle in heat-stressedbroilers. | J Sci Food Agric | 2018 Aug | 29315586 |
| Morphological alterations induced by the exposure to TiO<sub>2</sub> nanoparticles in primary cortical neuron cultures and in the brain of rats. | Toxicol Rep | 2018 | 30175048 |
| Structural basis of MsbA-mediated lipopolysaccharide transport. | Nature | 2017 Sep 14 | 28869968 |
| Functional Oil from Black Seed Differentially Inhibits Aldose-reductase andEctonucleotidase Activities by Up-regulating Cellular Energy inHaloperidol-induced Hepatic Toxicity in Rat Liver. | J Oleo Sci | 2017 Sep 1 | 28794311 |
| Diallyl trisulfide, a garlic polysulfide protects against As-induced renal oxidative nephrotoxicity, apoptosis and inflammation in rats by activating the Nrf2/ARE signaling pathway. | Int Immunopharmacol | 2017 Sep | 28648972 |
| Caffeine May Reduce Perceived Sweet Taste in Humans, Supporting Evidence ThatAdenosine Receptors Modulate Taste. | J Food Sci | 2017 Sep | 28833098 |
| Optogenetic Analysis of Depolarization-Dependent Glucagonlike Peptide-1 Release. | Endocrinology | 2017 Oct 1 | 28938466 |
| Toxicity of emerging antifouling biocides to non-target freshwater organisms from three trophic levels. | Aquat Toxicol | 2017 Oct | 28843204 |
Targets
- Uniprot ID:
- P08107
References
- Williamson DS, Borgognoni J, Clay A, Daniels Z, Dokurno P, Drysdale MJ, Foloppe N, Francis GL, Graham CJ, Howes R, Macias AT, Murray JB, Parsons R, Shaw T, Surgenor AE, Terry L, Wang Y, Wood M, Massey AJ: Novel adenosine-derived inhibitors of 70 kDa heat shock protein, discovered through structure-based design. J Med Chem. 2009 Mar 26;52(6):1510-3. doi: 10.1021/jm801627a. [19256508 ]
- General Function:
- Identical protein binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- ADORA2A
- Uniprot ID:
- P29274
- Molecular Weight:
- 44706.925 Da
References
- Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [20370662 ]
- General Function:
- G-protein coupled adenosine receptor activity
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
- Gene Name:
- ADORA3
- Uniprot ID:
- P0DMS8
- Molecular Weight:
- 36184.175 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Purine nucleoside binding
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name:
- ADORA1
- Uniprot ID:
- P30542
- Molecular Weight:
- 36511.325 Da
References
- Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [20370662 ]
- General Function:
- G-protein coupled adenosine receptor activity
- Specific Function:
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name:
- ADORA2B
- Uniprot ID:
- P29275
- Molecular Weight:
- 36332.655 Da
References
- Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [20370662 ]
- General Function:
- Rna binding
- Specific Function:
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
- Gene Name:
- IMPDH1
- Uniprot ID:
- P20839
- Molecular Weight:
- 55405.365 Da
References
- Chen L, Petrelli R, Olesiak M, Wilson DJ, Labello NP, Pankiewicz KW: Bis(sulfonamide) isosters of mycophenolic adenine dinucleotide analogues: inhibition of inosine monophosphate dehydrogenase. Bioorg Med Chem. 2008 Aug 1;16(15):7462-9. doi: 10.1016/j.bmc.2008.06.003. Epub 2008 Jun 10. [18583139 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase involved in various cellular processes such as regulation of the B-cell receptor (BCR) signalosome, oxidative stress-induced apoptosis, androgen receptor-dependent transcription regulation, insulin signaling and endothelial cells proliferation. Plays a key role in B-cell activation by regulating BCR-induced NF-kappa-B activation. Mediates the activation of the canonical NF-kappa-B pathway (NFKB1) by direct phosphorylation of CARD11/CARMA1 at 'Ser-559', 'Ser-644' and 'Ser-652'. Phosphorylation induces CARD11/CARMA1 association with lipid rafts and recruitment of the BCL10-MALT1 complex as well as MAP3K7/TAK1, which then activates IKK complex, resulting in nuclear translocation and activation of NFKB1. Plays a direct role in the negative feedback regulation of the BCR signaling, by down-modulating BTK function via direct phosphorylation of BTK at 'Ser-180', which results in the alteration of BTK plasma membrane localization and in turn inhibition of BTK activity. Involved in apoptosis following oxidative damage: in case of oxidative conditions, specifically phosphorylates 'Ser-36' of isoform p66Shc of SHC1, leading to mitochondrial accumulation of p66Shc, where p66Shc acts as a reactive oxygen species producer. Acts as a coactivator of androgen receptor (ANDR)-dependent transcription, by being recruited to ANDR target genes and specifically mediating phosphorylation of 'Thr-6' of histone H3 (H3T6ph), a specific tag for epigenetic transcriptional activation that prevents demethylation of histone H3 'Lys-4' (H3K4me) by LSD1/KDM1A. In insulin signaling, may function downstream of IRS1 in muscle cells and mediate insulin-dependent DNA synthesis through the RAF1-MAPK/ERK signaling cascade. May participate in the regulation of glucose transport in adipocytes by negatively modulating the insulin-stimulated translocation of the glucose transporter SLC2A4/GLUT4. Under high glucose in pancreatic beta-cells, is probably involved in the inhibition of the insulin gene transcription, via regulation of MYC expression. In endothelial cells, activation of PRKCB induces increased phosphorylation of RB1, increased VEGFA-induced cell proliferation, and inhibits PI3K/AKT-dependent nitric oxide synthase (NOS3/eNOS) regulation by insulin, which causes endothelial dysfunction. Also involved in triglyceride homeostasis (By similarity). Phosphorylates ATF2 which promotes cooperation between ATF2 and JUN, activating transcription.
- Gene Name:
- PRKCB
- Uniprot ID:
- P05771
- Molecular Weight:
- 76868.45 Da
References
- Loog M, Uri A, Raidaru G, Jarv J, Ek P: Adenosine-5'-carboxylic acid peptidyl derivatives as inhibitors of protein kinases. Bioorg Med Chem Lett. 1999 May 17;9(10):1447-52. [10360754 ]
- General Function:
- Peptidyl-cysteine s-nitrosylase activity
- Specific Function:
- Has both glyceraldehyde-3-phosphate dehydrogenase and nitrosylase activities, thereby playing a role in glycolysis and nuclear functions, respectively. Participates in nuclear events including transcription, RNA transport, DNA replication and apoptosis. Nuclear functions are probably due to the nitrosylase activity that mediates cysteine S-nitrosylation of nuclear target proteins such as SIRT1, HDAC2 and PRKDC. Modulates the organization and assembly of the cytoskeleton. Facilitates the CHP1-dependent microtubule and membrane associations through its ability to stimulate the binding of CHP1 to microtubules (By similarity). Glyceraldehyde-3-phosphate dehydrogenase is a key enzyme in glycolysis that catalyzes the first step of the pathway by converting D-glyceraldehyde 3-phosphate (G3P) into 3-phospho-D-glyceroyl phosphate. Component of the GAIT (gamma interferon-activated inhibitor of translation) complex which mediates interferon-gamma-induced transcript-selective translation inhibition in inflammation processes. Upon interferon-gamma treatment assembles into the GAIT complex which binds to stem loop-containing GAIT elements in the 3'-UTR of diverse inflammatory mRNAs (such as ceruplasmin) and suppresses their translation.
- Gene Name:
- GAPDH
- Uniprot ID:
- P04406
- Molecular Weight:
- 36053.0 Da
References
- Verlinde CL, Callens M, Van Calenbergh S, Van Aerschot A, Herdewijn P, Hannaert V, Michels PA, Opperdoes FR, Hol WG: Selective inhibition of trypanosomal glyceraldehyde-3-phosphate dehydrogenase by protein structure-based design: toward new drugs for the treatment of sleeping sickness. J Med Chem. 1994 Oct 14;37(21):3605-13. [7932587 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
- Gene Name:
- ADA
- Uniprot ID:
- P00813
- Molecular Weight:
- 40764.13 Da
References
- Bussolari JC, Ramesh K, Stoeckler JD, Chen SF, Panzica RP: Synthesis and biological evaluation of N4-substituted imidazo- and v-triazolo[4,5-d]pyridazine nucleosides. J Med Chem. 1993 Dec 10;36(25):4113-20. [8258836 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 Da
References
- Singh J, Dobrusin EM, Fry DW, Haske T, Whitty A, McNamara DJ: Structure-based design of a potent, selective, and irreversible inhibitor of the catalytic domain of the erbB receptor subfamily of protein tyrosine kinases. J Med Chem. 1997 Mar 28;40(7):1130-5. [9089334 ]
- General Function:
- Rna binding
- Specific Function:
- Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
- Gene Name:
- IMPDH2
- Uniprot ID:
- P12268
- Molecular Weight:
- 55804.495 Da
References
- Chen L, Petrelli R, Olesiak M, Wilson DJ, Labello NP, Pankiewicz KW: Bis(sulfonamide) isosters of mycophenolic adenine dinucleotide analogues: inhibition of inosine monophosphate dehydrogenase. Bioorg Med Chem. 2008 Aug 1;16(15):7462-9. doi: 10.1016/j.bmc.2008.06.003. Epub 2008 Jun 10. [18583139 ]