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; cn(c)C; cnc
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:60961; ChEMBL:CHEMBL477; 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 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit


Adenosine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49


Adenosine
ADMET 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 0.0
Number of Brenk structural alerts SwissADME 0.0
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
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000003084CFTR791
ENSP00000006053CX3CL1817
ENSP00000014930HEBP1900
ENSP00000019103SCTR900
ENSP00000176183DRD4928
ENSP00000176195SCT908
ENSP00000215832MAPK1724
ENSP00000216117HMOX1818
ENSP00000216629BDKRB1921
ENSP00000216911AURKA824
ENSP00000217305PDYN919
ENSP00000217386OXT838
ENSP00000217426AHCY998
ENSP00000218388TIMP1814
ENSP00000222248SLC5A5786
ENSP00000223642C5900
ENSP00000225992PPY900
ENSP00000226317CXCL6900
ENSP00000231188GRM6900
ENSP00000231751LTF741
ENSP00000234961OPRD1921
ENSP00000235628NT5C1A916
ENSP00000237527GHRH900
ENSP00000240615TAS2R8900
ENSP00000240619TAS2R10900
ENSP00000240652IAPP900
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000242152NPY926
ENSP00000242210NT5C3A900
ENSP00000243911MC3R921
ENSP00000245457PTGER2921
ENSP00000245552NT5C900
ENSP00000245907C3900
ENSP00000246115S1PR4900
ENSP00000246657CCR7909
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000249016MCHR1921
ENSP00000249041GALR3921
ENSP00000249284TAS2R16900
ENSP00000252723EPO842
ENSP00000254235ADCY7900
ENSP00000255008SSTR4921
ENSP00000255262NMUR2921
ENSP00000256906HRH4921
ENSP00000257068MTNR1B900
ENSP00000257254APLNR928
ENSP00000257497ANXA1900
ENSP00000257770NT5E994
ENSP00000258743IL6869
ENSP00000259607CCL21908
ENSP00000259631CCL27900
ENSP00000259667HINT2721
ENSP00000260600ADCY3900
ENSP00000261707SLC6A4815
ENSP00000261900CCNT1800
ENSP00000262027MARS701
ENSP00000262178VIPR2900
ENSP00000262441GLP2R900
ENSP00000262607CECR1823
ENSP00000262848PRKX715
ENSP00000262888KCNN4800
ENSP00000263025MAPK3765
ENSP00000263321TYR800
ENSP00000264218NMU900
ENSP00000264668MTRR911
ENSP00000264708POMC920
ENSP00000265023KNG1944
ENSP00000265132AMBP800
ENSP00000265343AFF4800
ENSP00000265572OPRK1935
ENSP00000265643GAL920
ENSP00000267377SSTR1929
ENSP00000267843FGF7800
ENSP00000269305TP53837
ENSP00000269980BCKDHA800
ENSP00000270631PTH2900
ENSP00000272190REN872
ENSP00000272644GPR17900
ENSP00000272847PTH2R900
ENSP00000272928ACKR3921
ENSP00000274353BHMT908
ENSP00000275216TAAR1921
ENSP00000276571CRH908
ENSP00000277120NTRK2912
ENSP00000278175ADM908
ENSP00000280155ADRA2A930
ENSP00000281806MCHR2921
ENSP00000282091PTH911
ENSP00000283558ATP11A822
ENSP00000284981APP908
ENSP00000286355ADCY8900
ENSP00000286621ADK999
ENSP00000286648DCK916
ENSP00000286749SLC28A1936
ENSP00000286758CXCL13900
ENSP00000287295AIFM1848
ENSP00000287641SST925
ENSP00000287907HTR5A921
ENSP00000289753HTR6921
ENSP00000291294PTGIR930
ENSP00000292174CXCR5900
ENSP00000292301CCR2927
ENSP00000292303CCR5930
ENSP00000293272CCL5912
ENSP00000293275CCL16900
ENSP00000293288BAX700
ENSP00000293330HCRT859
ENSP00000293778CXCL16900
ENSP00000293897SSTR5921
ENSP00000294016ADCY9900
ENSP00000294954LHCGR910
ENSP00000295683CXCR1900
ENSP00000296026CXCL3908
ENSP00000296027CXCL5900
ENSP00000296028PPBP900
ENSP00000296140CCR1921
ENSP00000297195SLC29A4921
ENSP00000297313RGS20900
ENSP00000297323ADCY1900
ENSP00000297469GPER1900
ENSP00000297494NOS3891
ENSP00000298171TSHR910
ENSP00000298386RXFP2908
ENSP00000298440OXGR1980
ENSP00000299727GALR1921
ENSP00000299766MC4R928
ENSP00000299964NNMT900
ENSP00000300061SCNN1G786
ENSP00000301908PNOC914
ENSP00000302079C3AR1900
ENSP00000302707FPR1900
ENSP00000302811MTNR1A900
ENSP00000302846PTGER4933
ENSP00000303147MAT2A818
ENSP00000303248RXFP1908
ENSP00000303424PTGDR921
ENSP00000304229HINT1824
ENSP00000304283RAC3815
ENSP00000304414CXCR6921
ENSP00000304501ADORA2B994
ENSP00000304767P2RY1953
ENSP00000304915IL13843
ENSP00000305372ADRB2978
ENSP00000305416S1PR1900
ENSP00000305464APLN900
ENSP00000305651CXCL10909
ENSP00000305877NMUR1921
ENSP00000306129DRD5921
ENSP00000306245FOS866
ENSP00000306512IL8983
ENSP00000306884CXCL11900
ENSP00000307259P2RY12942
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E921
ENSP00000308361P2RY14936
ENSP00000308549ADORA1999
ENSP00000308815CCL19900
ENSP00000309591PRKACA795
ENSP00000311032CASP3952
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000312304TPMT900
ENSP00000312999GNAI2914
ENSP00000313199HNRNPD854
ENSP00000313661HTR1D929
ENSP00000313681SPHK1818
ENSP00000315006SLC28A2947
ENSP00000315931AHCYL2968
ENSP00000316244HTR1A935
ENSP00000318077MC5R927
ENSP00000318916MARCO800
ENSP00000319635CXCR2913
ENSP00000319984CHRM2900
ENSP00000320180GHRHR900
ENSP00000320376P2RY13936
ENSP00000321999PTH1R900
ENSP00000322788MMP1800
ENSP00000322924HTR1F921
ENSP00000324248PENK908
ENSP00000325425MAT2B800
ENSP00000326432CCR8900
ENSP00000327246VIPR1927
ENSP00000327652935
ENSP00000327724TAS2R60900
ENSP00000327875LPAR5900
ENSP00000328472S1PR5900
ENSP00000328708RXFP3921
ENSP00000329684GALR2921
ENSP00000330032UPP1811
ENSP00000330070NPW900
ENSP00000330138SSTR3928
ENSP00000330237CASP9722
ENSP00000330284NPBWR1921
ENSP00000331746CALCA911
ENSP00000332225PMCH900
ENSP00000332448ADAT3928
ENSP00000332504CCR10900
ENSP00000332591NPY2R921
ENSP00000332659CCR4921
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000333821MC2R921
ENSP00000334050TAS2R42900
ENSP00000334145F3822
ENSP00000334448GNG2900
ENSP00000335074GHRL818
ENSP00000336630ADORA2A999
ENSP00000336764OPRL1921
ENSP00000337459NOS1851
ENSP00000337949HTR7944
ENSP00000338018HIF1A856
ENSP00000338072AVPR2921
ENSP00000339377NPY5R921
ENSP00000339393CCR6900
ENSP00000339479NT5C2982
ENSP00000339933PKLR800
ENSP00000340191FPR2900
ENSP00000340943CRHR2900
ENSP00000341821FPR3900
ENSP00000342560HRH3933
ENSP00000342952ADCY2942
ENSP00000343027GNAI1907
ENSP00000343428GPR18900
ENSP00000343782ADRB3968
ENSP00000344173GRM8900
ENSP00000344193RNASE1801
ENSP00000346017CALCB900
ENSP00000346671FYN817
ENSP00000346839FN1828
ENSP00000347197C5AR1900
ENSP00000347942RET800
ENSP00000348461RAC1814
ENSP00000348918SAA1900
ENSP00000349003PTGER3928
ENSP00000349478HCAR1900
ENSP00000350005GIP900
ENSP00000350024SLC29A2960
ENSP00000350198SSTR2921
ENSP00000350256CCR9921
ENSP00000350348GRM7900
ENSP00000350616DDC800
ENSP00000350878S1PR3900
ENSP00000351250TRIM33762
ENSP00000351273CASP8722
ENSP00000351671CCL20900
ENSP00000351755LPAR1928
ENSP00000352561CALCR900
ENSP00000352839NPSR1921
ENSP00000352904NT5C1B921
ENSP00000353198PYY900
ENSP00000353292SCNN1A786
ENSP00000353731DPP4889
ENSP00000353915HTR4921
ENSP00000354416CCL28900
ENSP00000354511COMT911
ENSP00000354532PNP992
ENSP00000354652NPY1R921
ENSP00000354859DRD2940
ENSP00000354901CXCL9900
ENSP00000355156SUCNR1900
ENSP00000355316GRM3908
ENSP00000355317WDTC1938
ENSP00000355523RGS7900
ENSP00000355536MTR909
ENSP00000355627AGT909
ENSP00000355890EPRS814
ENSP00000356213VIP918
ENSP00000356429RGS1900
ENSP00000356430RGS18910
ENSP00000357301RXFP4921
ENSP00000357459ADAR777
ENSP00000358099RGS10900
ENSP00000358301ADRB1970
ENSP00000358335MAP3K7800
ENSP00000358511CNR1939
ENSP00000358622IKBKG800
ENSP00000358730ADORA3989
ENSP00000358783NPBWR2921
ENSP00000358814AHCYL1968
ENSP00000358867GNAI3908
ENSP00000358963HTR1B928
ENSP00000359643LPAR3928
ENSP00000359665PI4K2A913
ENSP00000359719PRKACB741
ENSP00000360141GNAS912
ENSP00000360250ENTPD1778
ENSP00000360773SLC29A1967
ENSP00000360973AGTR2921
ENSP00000361125VEGFA956
ENSP00000361405MMP9824
ENSP00000361965ADA995
ENSP00000362285SLC29A3932
ENSP00000362353GLP1R907
ENSP00000362361CDK9831
ENSP00000362608PIM1800
ENSP00000362795CXCR3915
ENSP00000362888ADO739
ENSP00000363092PRKG1816
ENSP00000363296GRM4908
ENSP00000363431NPY4R921
ENSP00000363596CNR2927
ENSP00000363643P2RY4933
ENSP00000363822AR800
ENSP00000365413SLC28A3937
ENSP00000366061NMS900
ENSP00000366506HRH2921
ENSP00000367869900
ENSP00000367930OXER1900
ENSP00000368683EDN1841
ENSP00000369519MTAP709
ENSP00000369647AVP909
ENSP00000370648RDH14900
ENSP00000371084ATP8A1800
ENSP00000371932TAS2R1900
ENSP00000373169DRD3928
ENSP00000373674NT5M900
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000378492GRM2916
ENSP00000379086ADM2900
ENSP00000379110CXCL1907
ENSP00000379140CXCL12925
ENSP00000379213PTHLH900
ENSP00000379514ADCYAP1R1900
ENSP00000381105NPS916
ENSP00000381333CRHR1900
ENSP00000381339GNAT3900
ENSP00000383558GCGR900
ENSP00000384665LPAR2933
ENSP00000384708FSHR910
ENSP00000385834TF765
ENSP00000386069ADRA2C928
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14914
ENSP00000386884CXCR4986
ENSP00000387230UPP2741
ENSP00000387281ADRA2B921
ENSP00000387662GCG983
ENSP00000387699CREB1857
ENSP00000389948NT5C3B900
ENSP00000394624OPRM1949
ENSP00000397181RGS4900
ENSP00000398698TNF875
ENSP00000400175RHOA884
ENSP00000405095TAS2R39900
ENSP00000409007GDNF803
ENSP00000409378CHRM4910
ENSP00000410076CASP1824
ENSP00000411658ADCYAP1900
ENSP00000412237IL10857
ENSP00000413074ADAL974
ENSP00000419361ADCY5909
ENSP00000420194CASR908
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2908
ENSP00000428824GPBAR1900
ENSP00000430075AMPD1704
ENSP00000431418NTRK1914
ENSP00000431719TAS2R43900
ENSP00000433415NT5C1B-RDH14900
ENSP00000436450TAS2R46900
ENSP00000436714HCAR3900
ENSP00000441600CCR3921
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000444736TAS2R30900
ENSP00000448219TAS2R38900
ENSP00000451030RGS6900
ENSP00000451605MC1R921
ENSP00000466933S1PR2900
ENSP00000467494GIPR900
ENSP00000468991MTRNR2L12900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.