IMPPAT Phytochemical information: 
Melatonin

Melatonin
Summary

SMILES: COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
InChI: InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
InChIKey: DRLFMBDRBRZALE-UHFFFAOYSA-N
DeepSMILES: COcccccc6)cCCNC=O)C)))))c[nH]5
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CNC(C)=O; cOC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Indoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
melatonin
External chemical identifiers:
CID:896; ChEMBL:CHEMBL45; ChEBI:16796; ZINC:ZINC000000057060; FDASRS:JL5DK93RCL; SureChEMBL:SCHEMBL19018; MolPort-000-737-883
Chemical structure download


Melatonin
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


Melatonin
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 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.84


Melatonin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.59
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Melatonin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000008527CRY1937
ENSP00000014930HEBP1900
ENSP00000176183DRD4908
ENSP00000206249ESR1841
ENSP00000212015SIRT1849
ENSP00000216117HMOX1830
ENSP00000216629BDKRB1900
ENSP00000217305PDYN900
ENSP00000218316GPR50992
ENSP00000221130GSR888
ENSP00000222674NPVF816
ENSP00000222982CYP3A5800
ENSP00000223642C5900
ENSP00000225275MPO818
ENSP00000225371EPX800
ENSP00000225992PPY900
ENSP00000226317CXCL6900
ENSP00000226730IL2947
ENSP00000231188GRM6907
ENSP00000234961OPRD1900
ENSP00000240615TAS2R8900
ENSP00000240619TAS2R10900
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000242152NPY930
ENSP00000245907C3900
ENSP00000246115S1PR4900
ENSP00000246657CCR7915
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000248041CYP4F11800
ENSP00000248553HSPB1800
ENSP00000249016MCHR1900
ENSP00000249041GALR3911
ENSP00000249284TAS2R16900
ENSP00000250615AANAT986
ENSP00000254235ADCY7918
ENSP00000254657PER2927
ENSP00000255008SSTR4911
ENSP00000255262NMUR2900
ENSP00000256592TSHB822
ENSP00000256906HRH4900
ENSP00000257068MTNR1B999
ENSP00000257254APLNR900
ENSP00000257497ANXA1900
ENSP00000258400HTR2B836
ENSP00000258743IL6833
ENSP00000259271GAD2823
ENSP00000259607CCL21900
ENSP00000259631CCL27900
ENSP00000260408ADAM10800
ENSP00000260433CYP19A1896
ENSP00000260600ADCY3918
ENSP00000260630CYP1B1981
ENSP00000261707SLC6A4822
ENSP00000262367CREBBP816
ENSP00000262735PPARA815
ENSP00000263253EP300810
ENSP00000264218NMU982
ENSP00000264708POMC987
ENSP00000265023KNG1900
ENSP00000265572OPRK1900
ENSP00000265643GAL908
ENSP00000267377SSTR1911
ENSP00000269305TP53861
ENSP00000269571ERBB2819
ENSP00000270202AKT1951
ENSP00000272298CALM2830
ENSP00000272644GPR17900
ENSP00000272928ACKR3900
ENSP00000276414GNRH1855
ENSP00000280155ADRA2A900
ENSP00000281806MCHR2900
ENSP00000282397FLT1800
ENSP00000282561GJA1834
ENSP00000283916TMPRSS11D786
ENSP00000284981APP907
ENSP00000285979CYP2C18800
ENSP00000286355ADCY8933
ENSP00000286758CXCL13900
ENSP00000287641SST914
ENSP00000287907HTR5A917
ENSP00000291295CALM3800
ENSP00000292174CXCR5900
ENSP00000292301CCR2900
ENSP00000292303CCR5900
ENSP00000293272CCL5979
ENSP00000293275CCL16900
ENSP00000293778CXCL16900
ENSP00000293897SSTR5911
ENSP00000294016ADCY9900
ENSP00000295683CXCR1900
ENSP00000296026CXCL3900
ENSP00000296027CXCL5900
ENSP00000296028PPBP900
ENSP00000296140CCR1900
ENSP00000296545IL15847
ENSP00000297313RGS20910
ENSP00000297323ADCY1918
ENSP00000297469GPER1900
ENSP00000297494NOS3745
ENSP00000298171TSHR814
ENSP00000298440OXGR1900
ENSP00000299727GALR1900
ENSP00000299855MMP3800
ENSP00000301141CYP2A6900
ENSP00000301146CYP2A7800
ENSP00000301908PNOC900
ENSP00000302079C3AR1900
ENSP00000302150PRL899
ENSP00000302707FPR1900
ENSP00000302811MTNR1A999
ENSP00000303394HSPB3800
ENSP00000304414CXCR6900
ENSP00000305416S1PR1900
ENSP00000305464APLN900
ENSP00000305651CXCL10900
ENSP00000305877NMUR1900
ENSP00000306512IL8981
ENSP00000306884CXCL11900
ENSP00000307259P2RY12900
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E900
ENSP00000307786CYCS841
ENSP00000308032CYP2S1900
ENSP00000308361P2RY14900
ENSP00000308549ADORA1908
ENSP00000308815CCL19900
ENSP00000309103BAD700
ENSP00000311032CASP3949
ENSP00000311196NPAS4800
ENSP00000311405ADCY6918
ENSP00000312126ADCY4918
ENSP00000312455CFLAR800
ENSP00000312652LEP884
ENSP00000312999GNAI2915
ENSP00000313661HTR1D900
ENSP00000313681SPHK1800
ENSP00000314420PER1951
ENSP00000316244HTR1A968
ENSP00000319635CXCR2900
ENSP00000319984CHRM2900
ENSP00000320376P2RY13900
ENSP00000320866CALR800
ENSP00000321821CYP4F12800
ENSP00000322924HTR1F900
ENSP00000324248PENK900
ENSP00000324270OXTR800
ENSP00000324648CYP2B6800
ENSP00000326432CCR8900
ENSP00000327251NOS2782
ENSP00000327724TAS2R60900
ENSP00000327875LPAR5900
ENSP00000328472S1PR5900
ENSP00000328708RXFP3900
ENSP00000329684GALR2911
ENSP00000330070NPW900
ENSP00000330138SSTR3911
ENSP00000330237CASP9722
ENSP00000330284NPBWR1900
ENSP00000331574PDE1A800
ENSP00000332225PMCH900
ENSP00000332369ALAS2858
ENSP00000332504CCR10909
ENSP00000332591NPY2R900
ENSP00000332659CCR4900
ENSP00000332679CYP2A13800
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000333212CYP2U1900
ENSP00000333534CYP2F1800
ENSP00000334050TAS2R42900
ENSP00000334246CYP4Z1800
ENSP00000334448GNG2900
ENSP00000336764OPRL1900
ENSP00000337450CYP3A7800
ENSP00000337459NOS1922
ENSP00000337773NQO2968
ENSP00000338018HIF1A800
ENSP00000339377NPY5R900
ENSP00000339393CCR6900
ENSP00000339527FOXO3821
ENSP00000340191FPR2900
ENSP00000341821FPR3900
ENSP00000342007CYP1A2915
ENSP00000342560HRH3900
ENSP00000342952ADCY2932
ENSP00000343027GNAI1922
ENSP00000343428GPR18900
ENSP00000344173GRM8907
ENSP00000347197C5AR1900
ENSP00000347379OCLN800
ENSP00000348918SAA1900
ENSP00000349003PTGER3900
ENSP00000349467CALM1831
ENSP00000349478HCAR1900
ENSP00000350198SSTR2911
ENSP00000350256CCR9900
ENSP00000350348GRM7907
ENSP00000350878S1PR3900
ENSP00000351273CASP8724
ENSP00000351671CCL20900
ENSP00000351755LPAR1900
ENSP00000352273DIO3828
ENSP00000353198PYY900
ENSP00000353483MAPK8846
ENSP00000353820CYP2D6800
ENSP00000354416CCL28900
ENSP00000354558MTOR722
ENSP00000354652NPY1R900
ENSP00000354859DRD2908
ENSP00000354901CXCL9900
ENSP00000355031PER3801
ENSP00000355156SUCNR1900
ENSP00000355316GRM3900
ENSP00000355317WDTC1817
ENSP00000355523RGS7900
ENSP00000355627AGT900
ENSP00000356162KISS1859
ENSP00000356429RGS1900
ENSP00000356430RGS18900
ENSP00000356438PTGS2824
ENSP00000356694FASLG786
ENSP00000357206NES766
ENSP00000357301RXFP4900
ENSP00000358099RGS10900
ENSP00000358511CNR1900
ENSP00000358730ADORA3900
ENSP00000358783NPBWR2900
ENSP00000358867GNAI3922
ENSP00000358963HTR1B900
ENSP00000359643LPAR3900
ENSP00000360247CYP2J2800
ENSP00000360266JUN835
ENSP00000360317CYP2C8800
ENSP00000360372CYP2C19908
ENSP00000360968CYP4X1900
ENSP00000360973AGTR2900
ENSP00000360991CYP4B1800
ENSP00000361125VEGFA824
ENSP00000361141OPN4702
ENSP00000361405MMP9822
ENSP00000362795CXCR3900
ENSP00000362978EYA3824
ENSP00000363296GRM4907
ENSP00000363431NPY4R900
ENSP00000363512ALOX5800
ENSP00000363596CNR2900
ENSP00000363643P2RY4900
ENSP00000365280ID1800
ENSP00000366061NMS900
ENSP00000366093RORB900
ENSP00000367869900
ENSP00000367930OXER1900
ENSP00000367959HTR2A936
ENSP00000368683EDN1800
ENSP00000368752PRNP819
ENSP00000369050CYP1A1981
ENSP00000369547S100G800
ENSP00000370639ASMT986
ENSP00000371932TAS2R1900
ENSP00000373169DRD3900
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000376943BCL2L11800
ENSP00000377836GPC3800
ENSP00000378492GRM2900
ENSP00000379110CXCL1900
ENSP00000379140CXCL12900
ENSP00000380252NFE2L2818
ENSP00000381339GNAT3915
ENSP00000381758CAPN11786
ENSP00000384665LPAR2900
ENSP00000385806KCNMA1786
ENSP00000386069ADRA2C900
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14900
ENSP00000386884CXCR4900
ENSP00000387281ADRA2B900
ENSP00000387662GCG824
ENSP00000394624OPRM1900
ENSP00000397181RGS4900
ENSP00000398698TNF701
ENSP00000405095TAS2R39900
ENSP00000409007GDNF800
ENSP00000409378CHRM4900
ENSP00000412237IL10822
ENSP00000419361ADCY5918
ENSP00000419970POR900
ENSP00000420194CASR908
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2900
ENSP00000427336DIO3828
ENSP00000430432HDAC2844
ENSP00000430505IDO1900
ENSP00000431719TAS2R43900
ENSP00000435591MUC5AC800
ENSP00000436450TAS2R46900
ENSP00000436714HCAR3900
ENSP00000441600CCR3900
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000443432IDO2908
ENSP00000444736TAS2R30900
ENSP00000448165APAF1814
ENSP00000448219TAS2R38900
ENSP00000450980DIO2858
ENSP00000451030RGS6900
ENSP00000457706HSPB2-C11orf52800
ENSP00000466933S1PR2900
ENSP00000468991MTRNR2L12900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.