IMPPAT Phytochemical information: 
Phenethylamine

Phenethylamine
Summary

SMILES: NCCc1ccccc1
InChI: InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChIKey: BHHGXPLMPWCGHP-UHFFFAOYSA-N
DeepSMILES: NCCcccccc6
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CN
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Phenethylamines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Phenylethylamines
Synonymous chemical names:
beta-phenethylamine, phenethylamine, β-phenylethylamine
External chemical identifiers:
CID:1001; ChEMBL:CHEMBL610; ChEBI:18397; ZINC:ZINC000006579654; FDASRS:327C7L2BXQ; SureChEMBL:SCHEMBL968; MolPort-000-871-498
Chemical structure download


Phenethylamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 121.18
Log P RDKit 1.19
Topological polar surface area (Å2) RDKit 26.02
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 9
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 1
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 6
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.25
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 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
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 1


Phenethylamine
Drug-likeness properties
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 2
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 0.6245


Phenethylamine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.04
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


Phenethylamine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000019103SCTR900
ENSP00000176195SCT900
ENSP00000237527GHRH900
ENSP00000240652IAPP900
ENSP00000243911MC3R917
ENSP00000245457PTGER2917
ENSP00000253799AOC2970
ENSP00000254235ADCY7900
ENSP00000260600ADCY3900
ENSP00000262178VIPR2900
ENSP00000262441GLP2R900
ENSP00000264708POMC900
ENSP00000270349SLC6A3774
ENSP00000270631PTH2900
ENSP00000272847PTH2R900
ENSP00000275216TAAR1993
ENSP00000276571CRH900
ENSP00000278175ADM900
ENSP00000282091PTH900
ENSP00000286355ADCY8900
ENSP00000289753HTR6917
ENSP00000291294PTGIR917
ENSP00000293636CELA1794
ENSP00000294016ADCY9900
ENSP00000294954LHCGR900
ENSP00000297323ADCY1900
ENSP00000298171TSHR900
ENSP00000298386RXFP2900
ENSP00000299766MC4R917
ENSP00000302846PTGER4917
ENSP00000303248RXFP1900
ENSP00000303424PTGDR917
ENSP00000304501ADORA2B930
ENSP00000305372ADRB2917
ENSP00000306129DRD5917
ENSP00000308720PRSS1921
ENSP00000311405ADCY6900
ENSP00000312126ADCY4900
ENSP00000312326AOC3972
ENSP00000318077MC5R917
ENSP00000320180GHRHR900
ENSP00000321999PTH1R900
ENSP00000327246VIPR1900
ENSP00000327652917
ENSP00000331746CALCA900
ENSP00000333821MC2R917
ENSP00000334448GNG2900
ENSP00000336630ADORA2A947
ENSP00000337949HTR7944
ENSP00000338072AVPR2917
ENSP00000340684MAOA971
ENSP00000340943CRHR2900
ENSP00000342952ADCY2900
ENSP00000343782ADRB3917
ENSP00000345344CTSL800
ENSP00000346017CALCB900
ENSP00000350005GIP900
ENSP00000350616DDC927
ENSP00000352561CALCR900
ENSP00000352839NPSR1917
ENSP00000353915HTR4917
ENSP00000356213VIP900
ENSP00000358301ADRB1917
ENSP00000360141GNAS900
ENSP00000362353GLP1R900
ENSP00000366506HRH2917
ENSP00000367309MAOB974
ENSP00000367869900
ENSP00000369647AVP900
ENSP00000379086ADM2900
ENSP00000379213PTHLH900
ENSP00000379514ADCYAP1R1900
ENSP00000381105NPS900
ENSP00000381333CRHR1900
ENSP00000383558GCGR900
ENSP00000384708FSHR900
ENSP00000387662GCG900
ENSP00000411658ADCYAP1900
ENSP00000419361ADCY5900
ENSP00000428824GPBAR1900
ENSP00000451605MC1R917
ENSP00000467494GIPR900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.