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: c=O; cn(c)C; cnc
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:2519; ChEMBL:CHEMBL113; ChEBI:27732; ZINC:ZINC000000001084; FDASRS:3G6A5W338E; SureChEMBL:SCHEMBL5671
Chemical structure download


Caffeine
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


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 0.5385


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


Caffeine
Phytochemical - Predicted human target protein associations
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000014930HEBP1900
ENSP00000164139PYGM832
ENSP00000176183DRD4924
ENSP00000215909LGALS1800
ENSP00000216392PYGL882
ENSP00000216629BDKRB1924
ENSP00000217305PDYN900
ENSP00000219070MMP2800
ENSP00000222982CYP3A5890
ENSP00000223642C5900
ENSP00000225992PPY900
ENSP00000226317CXCL6900
ENSP00000227507CCND1800
ENSP00000231188GRM6900
ENSP00000234961OPRD1924
ENSP00000240615TAS2R8900
ENSP00000240619TAS2R10908
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000242152NPY908
ENSP00000245907C3900
ENSP00000246115S1PR4900
ENSP00000246657CCR7900
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000248041CYP4F11800
ENSP00000249016MCHR1924
ENSP00000249041GALR3924
ENSP00000249284TAS2R16900
ENSP00000254079PPP1R1B836
ENSP00000254235ADCY7900
ENSP00000255008SSTR4924
ENSP00000255262NMUR2924
ENSP00000256906HRH4924
ENSP00000257068MTNR1B916
ENSP00000257254APLNR924
ENSP00000257497ANXA1900
ENSP00000259607CCL21900
ENSP00000259631CCL27900
ENSP00000260600ADCY3900
ENSP00000260630CYP1B1817
ENSP00000262352SLC1A1800
ENSP00000263967PIK3CA800
ENSP00000264218NMU900
ENSP00000264708POMC982
ENSP00000265023KNG1914
ENSP00000265572OPRK1938
ENSP00000265643GAL908
ENSP00000266970CDK2891
ENSP00000267119KRT71733
ENSP00000267163RB1700
ENSP00000267377SSTR1924
ENSP00000269305TP53959
ENSP00000270202AKT1742
ENSP00000270349SLC6A3764
ENSP00000272190REN954
ENSP00000272644GPR17900
ENSP00000272928ACKR3924
ENSP00000276449STAR700
ENSP00000277120NTRK2800
ENSP00000278616ATM990
ENSP00000278968TAGLN800
ENSP00000280155ADRA2A924
ENSP00000281806MCHR2924
ENSP00000282091PTH822
ENSP00000284981APP900
ENSP00000285979CYP2C18800
ENSP00000286355ADCY8900
ENSP00000286479NAT2939
ENSP00000286758CXCL13900
ENSP00000287641SST907
ENSP00000287907HTR5A924
ENSP00000289153PIK3CB800
ENSP00000292174CXCR5900
ENSP00000292301CCR2924
ENSP00000292303CCR5924
ENSP00000293272CCL5900
ENSP00000293275CCL16900
ENSP00000293778CXCL16900
ENSP00000293897SSTR5924
ENSP00000294016ADCY9900
ENSP00000295600MITF800
ENSP00000295683CXCR1900
ENSP00000296026CXCL3900
ENSP00000296027CXCL5900
ENSP00000296028PPBP900
ENSP00000296140CCR1924
ENSP00000297313RGS20900
ENSP00000297323ADCY1900
ENSP00000297469GPER1917
ENSP00000297494NOS3819
ENSP00000298440OXGR1900
ENSP00000299727GALR1924
ENSP00000301141CYP2A6827
ENSP00000301146CYP2A7914
ENSP00000301908PNOC900
ENSP00000302079C3AR1900
ENSP00000302665IGF1835
ENSP00000302707FPR1900
ENSP00000302811MTNR1A916
ENSP00000304414CXCR6924
ENSP00000304501ADORA2B943
ENSP00000305416S1PR1900
ENSP00000305464APLN900
ENSP00000305651CXCL10900
ENSP00000305877NMUR1924
ENSP00000306245FOS825
ENSP00000306253ITPR1969
ENSP00000306390PRSS27800
ENSP00000306512IL8908
ENSP00000306884CXCL11900
ENSP00000307240KRT74733
ENSP00000307259P2RY12900
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E924
ENSP00000308032CYP2S1800
ENSP00000308361P2RY14900
ENSP00000308549ADORA1969
ENSP00000308815CCL19900
ENSP00000311032CASP3945
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000312999GNAI2900
ENSP00000313420PRKDC825
ENSP00000313661HTR1D924
ENSP00000314067PAK2917
ENSP00000316244HTR1A930
ENSP00000319635CXCR2900
ENSP00000319984CHRM2900
ENSP00000320376P2RY13900
ENSP00000320935SLC2A4818
ENSP00000321821CYP4F12800
ENSP00000322924HTR1F924
ENSP00000323740UCP3836
ENSP00000324248PENK900
ENSP00000324806GSK3B722
ENSP00000325875HSP90AB1768
ENSP00000326432CCR8900
ENSP00000327724TAS2R60900
ENSP00000327875LPAR5900
ENSP00000328472S1PR5900
ENSP00000328708RXFP3924
ENSP00000329539DUSP8800
ENSP00000329684GALR2924
ENSP00000330070NPW900
ENSP00000330138SSTR3924
ENSP00000330237CASP9812
ENSP00000330284NPBWR1924
ENSP00000331574PDE1A823
ENSP00000332116PDE4B800
ENSP00000332225PMCH900
ENSP00000332504CCR10900
ENSP00000332591NPY2R924
ENSP00000332659CCR4924
ENSP00000332679CYP2A13830
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000333534CYP2F1800
ENSP00000334050TAS2R42900
ENSP00000334246CYP4Z1800
ENSP00000334448GNG2900
ENSP00000335153HSP90AA1768
ENSP00000336630ADORA2A993
ENSP00000336764OPRL1924
ENSP00000337450CYP3A7890
ENSP00000337459NOS1786
ENSP00000337915CYP3A4938
ENSP00000338345SNCA753
ENSP00000339377NPY5R924
ENSP00000339393CCR6900
ENSP00000340191FPR2900
ENSP00000341821FPR3900
ENSP00000342007CYP1A2995
ENSP00000342560HRH3924
ENSP00000342952ADCY2917
ENSP00000343027GNAI1900
ENSP00000343428GPR18900
ENSP00000344173GRM8900
ENSP00000346762SND1821
ENSP00000347197C5AR1900
ENSP00000348918SAA1900
ENSP00000349003PTGER3924
ENSP00000349478HCAR1900
ENSP00000349709RAET1E800
ENSP00000350198SSTR2924
ENSP00000350256CCR9924
ENSP00000350348GRM7900
ENSP00000350878S1PR3900
ENSP00000351671CCL20900
ENSP00000351755LPAR1924
ENSP00000352608RYR1973
ENSP00000353198PYY900
ENSP00000353820CYP2D6902
ENSP00000354416CCL28900
ENSP00000354558MTOR760
ENSP00000354652NPY1R924
ENSP00000354859DRD2933
ENSP00000354901CXCL9900
ENSP00000355156SUCNR1900
ENSP00000355316GRM3900
ENSP00000355523RGS7900
ENSP00000355533RYR2967
ENSP00000355627AGT909
ENSP00000355759PARP1725
ENSP00000356429RGS1900
ENSP00000356430RGS18900
ENSP00000357301RXFP4924
ENSP00000358099RGS10900
ENSP00000358511CNR1937
ENSP00000358730ADORA3945
ENSP00000358783NPBWR2924
ENSP00000358867GNAI3900
ENSP00000358963HTR1B929
ENSP00000359643LPAR3924
ENSP00000360247CYP2J2800
ENSP00000360317CYP2C8818
ENSP00000360968CYP4X1800
ENSP00000360973AGTR2924
ENSP00000360991CYP4B1800
ENSP00000361125VEGFA819
ENSP00000361965ADA824
ENSP00000362795CXCR3900
ENSP00000363296GRM4900
ENSP00000363431NPY4R924
ENSP00000363435ITPR3838
ENSP00000363596CNR2924
ENSP00000363643P2RY4900
ENSP00000366061NMS900
ENSP00000366563PIK3CD800
ENSP00000367869900
ENSP00000367930OXER1900
ENSP00000369050CYP1A1986
ENSP00000369647AVP783
ENSP00000371932TAS2R1900
ENSP00000372023CHEK2855
ENSP00000373169DRD3932
ENSP00000373884RYR3963
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000377409SFTPB800
ENSP00000378492GRM2900
ENSP00000378699CDK1895
ENSP00000379110CXCL1900
ENSP00000379140CXCL12900
ENSP00000381339GNAT3900
ENSP00000384665LPAR2924
ENSP00000386069ADRA2C924
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14920
ENSP00000386884CXCR4924
ENSP00000387281ADRA2B924
ENSP00000387699CREB1818
ENSP00000388648CHEK1988
ENSP00000394624OPRM1937
ENSP00000397181RGS4900
ENSP00000405095TAS2R39900
ENSP00000409378CHRM4900
ENSP00000419361ADCY5922
ENSP00000420194CASR900
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2900
ENSP00000431719TAS2R43900
ENSP00000436450TAS2R46900
ENSP00000436714HCAR3900
ENSP00000441600CCR3924
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000444736TAS2R30900
ENSP00000447173VDR800
ENSP00000448219TAS2R38909
ENSP00000451030RGS6900
ENSP00000466933S1PR2900
ENSP00000468991MTRNR2L12900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.