IMPPAT Phytochemical information: 
Caffeine

Caffeine
Summary

SMILES: Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChI: InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
InChIKey: RYYVLZVUVIJVGH-UHFFFAOYSA-N
DeepSMILES: Cncncc5c=O)nC)c=O)n6C
Scaffold Graph/Node/Bond level: O=c1[nH]c(=O)c2[nH]cnc2[nH]1
Scaffold Graph/Node level: OC1NC(O)C2NCNC2N1
Scaffold Graph level: CC1CC(C)C2CCCC2C1
Functional groups: cn(C)c; cnc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Imidazopyrimidines
ClassyFire Subclass: Purines and purine derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Purine alkaloids
Synonymous chemical names:
1,3,7-tri-me-xanthine, caffeine
External chemical identifiers:
CID:CID_2519; ChEMBL:CHEMBL113; ChEBI:CHEBI:27732; ZINC:ZINC000000001084; FDASRS:3G6A5W338E; SureChEMBL:SCHEMBL5671
Chemical structure download


Caffeine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 194.19
Log P RDKit -1.03
Topological polar surface area (Å2) RDKit 61.82
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Caffeine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.538463


Caffeine
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 High
Log Kp (Skin permeation, cm/s) SwissADME -7.53
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


Caffeine
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_000523ENSG00000011677GABRA32556ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000520ENSG00000204681GABBR12550ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_000505ENSG00000198793MTOR2475BindingDB, NPASS
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000401ENSG00000163631ALB213ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000341ENSG00000136160EDNRB1910ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000524ENSG00000109158GABRA42557ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000525ENSG00000186297GABRA52558ChEMBL
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000579ENSG00000010310GIPR2696ChEMBL
TAR_EXP_000570ENSG00000288269GCGR2642ChEMBL
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000272ENSG00000138115CYP2C81558ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000270ENSG00000197408CYP2B61555ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000535ENSG00000094755GABRP2568ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000328ENSG00000169676DRD51816ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000526ENSG00000145863GABRA62559ChEMBL
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000534ENSG00000182256GABRG32567ChEMBL
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000532ENSG00000163285GABRG12565ChEMBL
TAR_EXP_000531ENSG00000102287GABRE2564ChEMBL
TAR_EXP_000530ENSG00000187730GABRD2563ChEMBL
TAR_EXP_000529ENSG00000166206GABRB32562ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000527ENSG00000163288GABRB12560ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_001332ENSG00000068976PYGM5837BindingDB, NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001249ENSG00000100600LGMN5641ChEMBL, NPASS
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001228ENSG00000253729PRKDC5591BindingDB, NPASS
TAR_EXP_001225ENSG00000268089GABRQ55879ChEMBL
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001156ENSG00000175054ATR545BindingDB, NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL, NPASS
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_001120ENSG00000171608PIK3CD5293ChEMBL, NPASS
TAR_EXP_001118ENSG00000051382PIK3CB5291NPASS
TAR_EXP_001117ENSG00000121879PIK3CA5290NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001063ENSG00000132915PDE6A5145ChEMBL
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001056ENSG00000065989PDE4A5141BindingDB
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001121ENSG00000105851PIK3CG5294BindingDB, NPASS
TAR_EXP_001451ENSG00000100739BDKRB1623ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001464ENSG00000198626RYR26262ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134BindingDB, ChEMBL, NPASS
TAR_EXP_000203ENSG00000128271ADORA2A135BindingDB, ChEMBL, NPASS
TAR_EXP_001921ENSG00000119125GDA9615BindingDB, ChEMBL, NPASS
TAR_EXP_001906ENSG00000118777ABCG29429BindingDB
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL
TAR_EXP_001683ENSG00000133742CA1759BindingDB
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000995ENSG00000101188NTSR14923ChEMBL
TAR_EXP_001538ENSG00000175003SLC22A16580ChEMBL, NPASS
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001615ENSG00000112333NR2E17101ChEMBL
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, NPASS
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000068ENSG00000164742ADCY1107ChEMBL, NPASS
TAR_EXP_000739ENSG00000148680HTR73363ChEMBL
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000112ENSG00000133063CHIT11118BindingDB
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000132ENSG00000137491SLCO2B111309ChEMBL, NPASS
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000237ENSG00000185269NOTUM147111ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140BindingDB, ChEMBL, NPASS
TAR_EXP_000212ENSG00000106113CRHR21395ChEMBL
TAR_EXP_000211ENSG00000276191CRHR11394ChEMBL
TAR_EXP_000204ENSG00000170425ADORA2B136BindingDB, ChEMBL, NPASS
TAR_EXP_000737ENSG00000157219HTR5A3361ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000947ENSG00000149311ATM472NPASS
TAR_EXP_000182ENSG00000023839ABCC21244NPASS
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL