IMPPAT Phytochemical information: 
Serotonin
Serotonin
Summary

SMILES: NCCc1c[nH]c2c1cc(O)cc2
InChI: InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2
InChIKey: QZAYGJVTTNCVMB-UHFFFAOYSA-N
DeepSMILES: NCCcc[nH]cc5ccO)cc6
Scaffold Graph/Node/Bond level: c1ccc2[nH]ccc2c1
Scaffold Graph/Node level: C1CCC2NCCC2C1
Scaffold Graph level: C1CCC2CCCC2C1
Functional groups: CN; cO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Tryptamines and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
tryptamine,5-hydroxy, serotonin, 5-hydroxy-tryptamine, tryptamine, 5-hydroxy, serotonine, 5-hydroxytryptamine
External chemical identifiers:
CID:CID_5202; ChEMBL:CHEMBL39; ChEBI:CHEBI:28790; ZINC:ZINC000000057058; FDASRS:333DO1RDJY; SureChEMBL:SCHEMBL1495; MolPort-001-779-633
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Serotonin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 176.22
Log P RDKit 1.37
Topological polar surface area (Å2) RDKit 62.04
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 3
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 8
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
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
Serotonin
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 0.646845
Serotonin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.32
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
Serotonin
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_000731ENSG00000179097HTR1F3355BindingDB, ChEMBL, NPASS
TAR_EXP_000730ENSG00000168830HTR1E3354BindingDB, ChEMBL, NPASS
TAR_EXP_000729ENSG00000179546HTR1D3352BindingDB, ChEMBL, NPASS
TAR_EXP_000728ENSG00000135312HTR1B3351BindingDB, ChEMBL, NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350BindingDB, ChEMBL, NPASS
TAR_EXP_000624ENSG00000186038HTR3E285242ChEMBL
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000492ENSG00000118298CA1423632ChEMBL, NPASS
TAR_EXP_000737ENSG00000157219HTR5A3361ChEMBL, NPASS
TAR_EXP_000733ENSG00000135914HTR2B3357BindingDB, ChEMBL, NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL, NPASS
TAR_EXP_001534ENSG00000165646SLC18A26571BindingDB, ChEMBL, NPASS
TAR_EXP_001539ENSG00000146477SLC22A36581ChEMBL
TAR_EXP_001540ENSG00000112499SLC22A26582ChEMBL, NPASS
TAR_EXP_001631ENSG00000165409TSHR7253ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001656ENSG00000156096UGT2B47363ChEMBL, NPASS
TAR_EXP_001657ENSG00000171234UGT2B77364ChEMBL, NPASS
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001519ENSG00000142319SLC6A36531BindingDB
TAR_EXP_001660ENSG00000197888UGT2B177367ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760ChEMBL, NPASS
TAR_EXP_001685ENSG00000164879CA3761ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762ChEMBL, NPASS
TAR_EXP_001687ENSG00000174990CA5A763ChEMBL, NPASS
TAR_EXP_001688ENSG00000131686CA6765ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771ChEMBL, NPASS
TAR_EXP_001880ENSG00000149305HTR3B9177ChEMBL
TAR_EXP_001683ENSG00000133742CA1759ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999NPASS
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001313ENSG00000007047MARK457787BindingDB, ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358BindingDB, ChEMBL, NPASS
TAR_EXP_000735ENSG00000166736HTR3A3359BindingDB, ChEMBL, NPASS
TAR_EXP_000736ENSG00000164270HTR43360ChEMBL, NPASS
TAR_EXP_000464ENSG00000037280FLT42324BindingDB
TAR_EXP_000738ENSG00000158748HTR63362BindingDB, ChEMBL, NPASS
TAR_EXP_000739ENSG00000148680HTR73363BindingDB, ChEMBL, NPASS
TAR_EXP_000750ENSG00000140443IGF1R3480BindingDB
TAR_EXP_000810ENSG00000128052KDR3791BindingDB
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000876ENSG00000276701MIF4282BindingDB
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL, NPASS
TAR_EXP_000914ENSG00000168412MTNR1A4543BindingDB, ChEMBL, NPASS
TAR_EXP_000915ENSG00000134640MTNR1B4544BindingDB, ChEMBL, NPASS
TAR_EXP_000975ENSG00000124588NQO24835BindingDB
TAR_EXP_001157ENSG00000143190POU2F15451ChEMBL
TAR_EXP_001158ENSG00000028277POU2F25452ChEMBL
TAR_EXP_001163ENSG00000167165UGT1A654578ChEMBL
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356BindingDB, ChEMBL, NPASS
TAR_EXP_000362ENSG00000186090HTR3D200909ChEMBL
TAR_EXP_000202ENSG00000146399TAAR1134864BindingDB, ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813BindingDB, ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000308ENSG00000178084HTR3C170572ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000122ENSG00000169239CA5B11238ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB