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: cOC; CNC(C)=O; 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:CID_896; ChEMBL:CHEMBL45; ChEBI: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 232.28
Log P RDKit 1.86
Topological polar surface area (Å2) RDKit 54.12
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
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 9
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.31
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
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


Melatonin
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 0
Ghose filter RDKit Passed
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 0.844935


Melatonin
ADME 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
Number of Brenk structural alerts SwissADME 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
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_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000257ENSG00000168329CX3CR11524ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000239ENSG00000120907ADRA1A148ChEMBL
TAR_EXP_000237ENSG00000185269NOTUM147111ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000341ENSG00000136160EDNRB1910ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544BindingDB, ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000333ENSG00000134817APLNR187ChEMBL
TAR_EXP_000262ENSG00000140465CYP1A11543BindingDB, ChEMBL, NPASS
TAR_EXP_000337ENSG00000170989S1PR11901ChEMBL
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244NPASS
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000125ENSG00000101180HRH311255BindingDB, ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL
TAR_EXP_000039ENSG00000125257ABCC410257BindingDB, NPASS
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000405ENSG00000180210F22147ChEMBL
TAR_EXP_000211ENSG00000276191CRHR11394ChEMBL
TAR_EXP_000213ENSG00000147262GPR119139760ChEMBL
TAR_EXP_000439ENSG00000068078FGFR32261ChEMBL
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_000477ENSG00000141867BRD423476ChEMBL
TAR_EXP_000488ENSG00000171049FPR22358ChEMBL
TAR_EXP_000509ENSG00000097007ABL125ChEMBL
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000570ENSG00000288269GCGR2642ChEMBL
TAR_EXP_000575ENSG00000153292ADGRF1266977ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000227ENSG00000141551CSNK1D1453ChEMBL
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000212ENSG00000106113CRHR21395ChEMBL
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_001825ENSG00000122779TRIM248805ChEMBL
TAR_EXP_001816ENSG00000108846ABCC38714BindingDB, NPASS
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_001709ENSG00000156983BRPF17862ChEMBL
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001684ENSG00000104267CA2760ChEMBL
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_001639ENSG00000197405C5AR1728ChEMBL
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_001574ENSG00000087586AURKA6790ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_001839ENSG00000110148CCKBR887ChEMBL
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_000977ENSG00000089250NOS14842ChEMBL
TAR_EXP_000975ENSG00000124588NQO24835BindingDB, ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000915ENSG00000134640MTNR1B4544BindingDB, ChEMBL, NPASS
TAR_EXP_000914ENSG00000168412MTNR1A4543BindingDB, ChEMBL, NPASS
TAR_EXP_000896ENSG00000005381MPO4353BindingDB, ChEMBL, NPASS
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000995ENSG00000101188NTSR14923ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001056ENSG00000065989PDE4A5141ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001451ENSG00000100739BDKRB1623ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000744ENSG00000186188FFAR4338557ChEMBL
TAR_EXP_000743ENSG00000182782HCAR2338442ChEMBL
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358BindingDB, ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357BindingDB, ChEMBL
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000626ENSG00000178623GPR352859ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740ChEMBL
TAR_EXP_000579ENSG00000010310GIPR2696ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000773ENSG00000169083AR367ChEMBL
TAR_EXP_000759ENSG00000169429CXCL83576NPASS
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL
TAR_EXP_001378ENSG00000143365RORC6097NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL