Adenosine



Compound IDCDAMM00323
Common nameAdenosine
IUPAC name(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Molecular formulaC10H13N5O4

Experimental data

Retention time10.942
Adduct[M+H]+
Actual mz268.105
Theoretical mz268.104
Error2.87
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.01

Identifiers and class information

Inchi keyOIRDTQYFTABQOQ-KQYNXXCUSA-N
SmilesOCC1OC(N2C=NC=3C(=NC=NC32)N)C(O)C1O
SuperclassNucleosides, nucleotides, and analogues
ClassPurine nucleosides

Pharmacokinetic properties

Number of descriptor values(#stars)0
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)0
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)5
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)267.244
Computed dipole moment(dipole)7.904
Total solvent accessible surface area (SASA)473.676
Hydrophobic component of SASA (FOSA)95.984
Hydrophilic component of SASA (FISA)275.715
Pie component of the SASA (PISA)101.977
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)794.227
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)10.8
Free energy of solvation of dipole (dip^2/V)0.0786529
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0509832
Globularity descriptor (glob)0.875615
Predicted polarizability in cubic angstroms (QPpolrz)23.394
Predicted hexadecane/gas partition coefficient (QPlogPC16)9.397
Predicted octanol/gas partition coefficient (QPlogPoct)22.086
Predicted water/gas partition coefficient (QPlogPw)20.286
Predicted octanol/water partition coefficient (QPlogPo/w)-1.81
Predicted aqueous solubility (QPlogS)-1.813
Conformation-independent predicted aqueous solubility (CIQPlogS)-1.506
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.031
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)24.06
Predicted brain/blood partition coefficient (QPlogBB)-2.135
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)8.805
Predicted skin permeability, log Kp (QPlogKp)-5.762
PM3 calculated ionization potential (IP(ev))8.453
PM3 calculated electron affinity (EA(eV))0.208
Number of likely metabolic reactions (#metab)5
Prediction of binding to human serum albumin (QPlogKhsa)-0.89
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)41.072
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)142.606
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)0
Number of violations of Jorgensen’s rule of three (RuleOfThree)0

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
Q86X55CARM1Histone-arginine methyltransferase CARM1T12837SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction and SEA
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction and SEA
P07327ADH1AAlcohol dehydrogenase alpha chainT65570SEA
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction and SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction and SEA
P11086PNMTPhenylethanolamine N-methyltransferaseT56496SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction and SEA
P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction and SEA
P04183TK1Thymidine kinase, cytosolicT30081SEA
P14902IDO1Indoleamine 2,3-dioxygenaseT89697SwissTargetPrediction
P49137MAPKAPK2MAP kinase-activated protein kinase 2T21307SwissTargetPrediction
P09467FBP1Fructose-1,6-bisphosphataseT83391SwissTargetPrediction and SEA
P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
P14061HSD17B1Estradiol 17-beta-dehydrogenase 1T44011SwissTargetPrediction
P0DMV8HSPA1AHeat shock 70 kDa protein 1T49639SwissTargetPrediction
P12931SRCTyrosine-protein kinase SRCT85943SwissTargetPrediction
P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SwissTargetPrediction
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SEA
P32320CDACytidine deaminase (by homology)T79027SwissTargetPrediction and SEA
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction and SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P28482MAPK1MAP kinase ERK2T58970SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction and SEA
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction and SEA
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction and SEA
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction and SEA
P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction and SEA
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
Q9H244P2RY12Purinergic receptor P2Y12 (by homology)T46937SEA
P19971TYMPThymidine phosphorylaseT59929SEA
Q8TEK3DOT1LHistone-lysine N-methyltransferase, H3 lysine-79 specificT87686SwissTargetPrediction and SEA
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SEA
P55786NPEPPSPuromycin-sensitive aminopeptidaseT15610SEA
P47900P2RY1Purinergic receptor P2Y1T67818SwissTargetPrediction and SEA
P41231P2RY2Purinergic receptor P2Y2T93515SEA
P63000RAC1Ras-related C3 botulinum toxin substrate 1T88752SEA
Q15910EZH2EZH2/SUZ12/EED/RBBP7/RBBP4T25265SwissTargetPrediction and SEA
Q99873PRMT1Protein-arginine N-methyltransferase 1T16808SwissTargetPrediction and SEA
Q96KQ7EHMT2Histone-lysine N-methyltransferase, H3 lysine-9 specific 3T53251SwissTargetPrediction and SEA
P16885PLCG2Phospholipase C-gamma-2T93922SEA
Q9Y478PRKAB1AMP-activated protein kinase, beta-1 subunitT38875SEA
Q13126MTAPS-methyl-5-thioadenosine phosphorylaseT40787SwissTargetPrediction
P06865HEXABeta-hexosaminidase subunit alphaT63196SEA
P07686HEXBBeta-N-acetyl-D-hexosaminidase-A/BT63197SEA
P23919DTYMKThymidylate kinaseT94400SEA
Q9NRG4SMYD2N-lysine methyltransferase SMYD2T15797SwissTargetPrediction and SEA
O94759TRPM2Transient receptor potential cation channel subfamily M member 2T78205SEA
P41252IARSIsoleucyl-tRNA synthetaseT46515SwissTargetPrediction
Q9H9B1EHMT1Histone-lysine N-methyltransferase, H3 lysine-9 specific 5T39996SwissTargetPrediction and SEA
Q9UBC3DNMT3BDNA (cytosine-5)-methyltransferase 3BT65501SwissTargetPrediction and SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
P49789FHITBis(5'-adenosyl)-triphosphataseT59720SwissTargetPrediction
Q05823RNASELRNase LT25200SEA
P51575P2RX1P2X purinoceptor 1T69091SwissTargetPrediction and SEA
P17707AMD1S-adenosylmethionine decarboxylase 1T55922SwissTargetPrediction and SEA
Q8WTS6SETD7Histone-lysine N-methyltransferase SETD7T73184SwissTargetPrediction and SEA
Q9NVM4PRMT7Protein arginine N-methyltransferase 7T79501SwissTargetPrediction and SEA
Q9BYW2SETD2Histone-lysine N-methyltransferase SETD2T73551SwissTargetPrediction
O43463SUV39H1Histone-lysine N-methyltransferase SUV39H1T39519SwissTargetPrediction and SEA
Q92800EZH1Histone-lysine N-methyltransferase EZH1T17986SwissTargetPrediction and SEA
Q99571P2RX4P2X purinoceptor 4T60330SEA
Q13304GPR17Uracil nucleotide/cysteinyl leukotriene receptorT33902SEA
Q86Y97KMT5CHistone-lysine N-methyltransferase KMT5CT68490SEA
O95622ADCY5Adenylate cyclase type 5T19531SEA
Q9NZ70TAK1TGF-beta-activated kinase 1T04361SEA
Q9Y4W7PARGPoly(ADP-ribose) glycohydrolaseT66935SwissTargetPrediction and SEA
Q07108CD69Early activation antigen CD69T48780SEA
O60755GALR3Galanin receptorT98494SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T65570DI0139Exposure to noxious substances harmful effect[ICD-11: NE61]P07327ADH1A
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
T78198DI0167Gout[ICD-11: FA25]P00491PNP
T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
T30081DI0012Acute myeloid leukaemia[ICD-11: 2A60]P04183TK1
T30081DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P04183TK1
T89697DI0117Depression[ICD-11: 6A70-6A7Z]P14902IDO1
T21307DI0011Acute laryngitis/tracheitis[ICD-11: CA05]P49137MAPKAPK2
T21307DI0181Hidradenitis suppurativa[ICD-11: ED92]P49137MAPKAPK2
T21307DI0269Monogenic autoinflammatory syndrome[ICD-11: 4A60]P49137MAPKAPK2
T21307DI0334Peritoneal cancer[ICD-11: 2C51]P49137MAPKAPK2
T21307DI0352Psoriatic arthritis[ICD-11: FA21]P49137MAPKAPK2
T21307DI0366Rheumatoid arthritis[ICD-11: FA20]P49137MAPKAPK2
T21307DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P49137MAPKAPK2
T83391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P09467FBP1
T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
T49639DI0121Diabetic foot ulcer[ICD-11: BD54]P0DMV8HSPA1A
T49639DI0180Herpes simplex infection[ICD-11: 1F00]P0DMV8HSPA1A
T49639DI0231Leukaemia[ICD-11: 2A60-2B33]P0DMV8HSPA1A
T49639DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P0DMV8HSPA1A
T49639DI0260Metastatic malignant neoplasm[ICD-11: 2D50-2E09]P0DMV8HSPA1A
T49639DI0298Neuropathy[ICD-11: 8C0Z]P0DMV8HSPA1A
T49639DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMV8HSPA1A
T49639DI0395Stomach cancer[ICD-11: 2B72]P0DMV8HSPA1A
T85943DI0062Breast cancer[ICD-11: 2C60-2C6Y]P12931SRC
T85943DI0220Ischemia[ICD-11: 8B10-8B11]P12931SRC
T85943DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P12931SRC
T85943DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P12931SRC
T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T58970DI0036Arteries/arterioles disorder[ICD-11: BD52]P28482MAPK1
T58970DI0252Melanoma[ICD-11: 2C30]P28482MAPK1
T58970DI0326Pancreatic cancer[ICD-11: 2C10]P28482MAPK1
T58970DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P28482MAPK1
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
T46937DI0287Myocardial infarction[ICD-11: BA41-BA43]Q9H244P2RY12
T46937DI0405Thrombosis[ICD-11: DB61-GB90]Q9H244P2RY12
T59929DI0117Depression[ICD-11: 6A70-6A7Z]P19971TYMP
T87686DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q8TEK3DOT1L
T87686DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q8TEK3DOT1L
T87686DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q8TEK3DOT1L
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T15610DI0012Acute myeloid leukaemia[ICD-11: 2A60]P55786NPEPPS
T15610DI0284Myelodysplastic syndrome[ICD-11: 2A37]P55786NPEPPS
T93515DI0436Visual system disease[ICD-11: 9E1Z]P41231P2RY2
T88752DI0025Alzheimer disease[ICD-11: 8A20]P63000RAC1
T25265DI0151Follicular lymphoma[ICD-11: 2A80]Q15910EZH2
T16808DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q99873PRMT1
T53251DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q96KQ7EHMT2
T53251DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q96KQ7EHMT2
T53251DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96KQ7EHMT2
T38875DI0009Acute diabete complication[ICD-11: 5A2Y]Q9Y478PRKAB1
T40787DI0275Multiple sclerosis[ICD-11: 8A40]Q13126MTAP
T63196DI0242Lysosomal disease[ICD-11: 5C56]P06865HEXA
T63197DI0242Lysosomal disease[ICD-11: 5C56]P07686HEXB
T15797DI0238Lung cancer[ICD-11: 2C25]Q9NRG4SMYD2
T15797DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9NRG4SMYD2
T39996DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q9H9B1EHMT1
T39996DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H9B1EHMT1
T65501DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UBC3DNMT3B
T59720DI0293Nausea/vomiting[ICD-11: MD90]P49789FHIT
T55922DI0004Acidosis[ICD-11: 5C73]P17707AMD1
T73184DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q8WTS6SETD7
T17986DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q92800EZH1
T17986DI0238Lung cancer[ICD-11: 2C25]Q92800EZH1
T17986DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q92800EZH1
T17986DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q92800EZH1
T17986DI0251Mature T-cell lymphoma[ICD-11: 2A90]Q92800EZH1
T17986DI0361Renal cell carcinoma[ICD-11: 2C90]Q92800EZH1
T17986DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92800EZH1
T17986DI0423Ureteral cancer[ICD-11: 2C92]Q92800EZH1
T04361DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9NZ70TAK1
T98494DI0265Mild neurocognitive disorder[ICD-11: 6D71]O60755GALR3

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