IMPPAT Phytochemical information: 
Adenosine

Adenosine
Summary

SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
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
InChIKey: OIRDTQYFTABQOQ-KQYNXXCUSA-N
DeepSMILES: OC[C@H]O[C@H][C@@H][C@@H]5O))O))ncncc5ncnc6N
Scaffold Graph/Node/Bond level: c1ncc2ncn(C3CCCO3)c2n1
Scaffold Graph/Node level: C1COC(N2CNC3CNCNC32)C1
Scaffold Graph level: C1CCC2C(C1)CCC2C1CCCC1
Functional groups: CO; COC; cn(C)c; cnc; cN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Nucleosides, nucleotides, and analogues
ClassyFire Class: Purine nucleosides
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Nucleosides
NP Classifier Class: Purine nucleos(t)ides
Synonymous chemical names:
adenosine
External chemical identifiers:
CID:CID_60961; ChEMBL:CHEMBL477; ChEBI:CHEBI:16335; ZINC:ZINC000002169830; FDASRS:K72T3FS567; SureChEMBL:SCHEMBL731; MolPort-001-838-229
Chemical structure download


Adenosine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 267.25
Log P RDKit -1.98
Topological polar surface area (Å2) RDKit 139.54
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 5
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Adenosine
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49052


Adenosine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.68
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Adenosine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000214ENSG00000282608ADORA3140BindingDB, ChEMBL, NPASS
TAR_EXP_000227ENSG00000141551CSNK1D1453ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000257ENSG00000168329CX3CR11524ChEMBL
TAR_EXP_000213ENSG00000147262GPR119139760ChEMBL
TAR_EXP_000626ENSG00000178623GPR352859ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135BindingDB, ChEMBL, NPASS
TAR_EXP_000200ENSG00000163485ADORA1134BindingDB, ChEMBL, NPASS
TAR_EXP_000333ENSG00000134817APLNR187ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000001ENSG00000196839ADA100BindingDB, ChEMBL, NPASS
TAR_EXP_000204ENSG00000170425ADORA2B136BindingDB, ChEMBL, NPASS
TAR_EXP_000197ENSG00000156110ADK132ChEMBL, NPASS
TAR_EXP_000337ENSG00000170989S1PR11901ChEMBL
TAR_EXP_000340ENSG00000101444AHCY191ChEMBL, NPASS
TAR_EXP_000439ENSG00000068078FGFR32261ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001825ENSG00000122779TRIM248805ChEMBL
TAR_EXP_001773ENSG00000104885DOT1L84444BindingDB, ChEMBL, NPASS
TAR_EXP_001709ENSG00000156983BRPF17862ChEMBL
TAR_EXP_001639ENSG00000197405C5AR1728ChEMBL
TAR_EXP_001627ENSG00000166598HSP90B17184ChEMBL, NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000440ENSG00000066468FGFR22263ChEMBL, NPASS
TAR_EXP_001589ENSG00000135341MAP3K76885BindingDB, ChEMBL, NPASS
TAR_EXP_001570ENSG00000166888STAT66778NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001484ENSG00000197506SLC28A364078BindingDB, ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001372ENSG00000115665SLC5A760482ChEMBL, NPASS
TAR_EXP_001574ENSG00000087586AURKA6790ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000441ENSG00000160867FGFR42264ChEMBL
TAR_EXP_000477ENSG00000141867BRD423476ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB, NPASS
TAR_EXP_000367ENSG00000112759SLC29A12030BindingDB, ChEMBL, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000438ENSG00000077782FGFR12260ChEMBL
TAR_EXP_001877ENSG00000156222SLC28A19154BindingDB, ChEMBL, NPASS
TAR_EXP_001876ENSG00000137860SLC28A29153BindingDB, ChEMBL, NPASS
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_000604ENSG00000112164GLP1R2740ChEMBL
TAR_EXP_000575ENSG00000153292ADGRF1266977ChEMBL
TAR_EXP_000556ENSG00000111640GAPDH2597BindingDB, ChEMBL, NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000509ENSG00000097007ABL125ChEMBL
TAR_EXP_000488ENSG00000171049FPR22358ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001209ENSG00000166501PRKCB5579BindingDB, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000904ENSG00000099810MTAP4507ChEMBL, NPASS
TAR_EXP_000982ENSG00000198805PNP4860BindingDB, ChEMBL, NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001078ENSG00000113721PDGFRB5159ChEMBL, NPASS
TAR_EXP_001104ENSG00000170950PGK25232NPASS
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001123ENSG00000241973PI4KA5297ChEMBL, NPASS
TAR_EXP_001248ENSG00000165819METTL356339ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001124ENSG00000143393PI4KB5298ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001189ENSG00000155252PI4K2A55361ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_001187ENSG00000038210PI4K2B55300ChEMBL
TAR_EXP_000770ENSG00000171105INSR3643ChEMBL, NPASS
TAR_EXP_000764ENSG00000106348IMPDH13614BindingDB, ChEMBL, NPASS
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL
TAR_EXP_000698ENSG00000174669SLC29A23177NPASS
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000714ENSG00000234475HSPA1A3303BindingDB
TAR_EXP_000765ENSG00000178035IMPDH23615BindingDB, ChEMBL, NPASS
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_000718ENSG00000109971HSPA83312BindingDB, NPASS
TAR_EXP_000722ENSG00000080824HSP90AA13320BindingDB, ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000744ENSG00000186188FFAR4338557ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417NPASS