IMPPAT Phytochemical information: 
Norepinephrine

Norepinephrine
Summary

SMILES: NC[C@@H](c1ccc(c(c1)O)O)O
InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N
DeepSMILES: NC[C@@H]cccccc6)O))O)))))O
Scaffold Graph/Node/Bond level: c1ccccc1
Scaffold Graph/Node level: C1CCCCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CN; CO; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Benzenediols
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Phenylethylamines
Synonymous chemical names:
l-noradrenaline, neopinephrine (noradrenaline), noradrenaline, norepinephrine, norepinephrine (ne), norepinephrine (noradrenaline)
External chemical identifiers:
CID:439260; ChEMBL:CHEMBL1437; ChEBI:18357; ZINC:ZINC000000057624; FDASRS:X4W3ENH1CV; SureChEMBL:SCHEMBL2609; MolPort-003-666-243
Chemical structure download


Norepinephrine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 169.18
Log P RDKit 0.09
Topological polar surface area (Å2) RDKit 86.71
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.12
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


Norepinephrine
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4724


Norepinephrine
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 -8.21
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 1.0
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


Norepinephrine
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000014930HEBP1900
ENSP00000019103SCTR900
ENSP00000054668UTS2907
ENSP00000078429GNA11925
ENSP00000171757P2RY10900
ENSP00000176183DRD4954
ENSP00000176195SCT912
ENSP00000206262RGS17900
ENSP00000216629BDKRB1922
ENSP00000217270PROKR2922
ENSP00000217305PDYN934
ENSP00000217386OXT947
ENSP00000218721MLNR922
ENSP00000219833SLC6A2990
ENSP00000222256RAB3A900
ENSP00000223095SERPINE1829
ENSP00000223642C5900
ENSP00000225992PPY943
ENSP00000226317CXCL6900
ENSP00000226413GNRHR922
ENSP00000229794MAPK14710
ENSP00000231188GRM6900
ENSP00000231509NR3C1759
ENSP00000234371KISS1R922
ENSP00000234961OPRD1929
ENSP00000235382RGS2907
ENSP00000237527GHRH911
ENSP00000240615TAS2R8900
ENSP00000240619TAS2R10900
ENSP00000240652IAPP909
ENSP00000240687TAS2R7900
ENSP00000240691TAS2R9900
ENSP00000240874KALRN900
ENSP00000241256GHSR940
ENSP00000242152NPY975
ENSP00000243911MC3R934
ENSP00000245457PTGER2922
ENSP00000245907C3900
ENSP00000245983GNRH2900
ENSP00000246115S1PR4900
ENSP00000246549FFAR2900
ENSP00000246553FFAR1900
ENSP00000246657CCR7900
ENSP00000247879TAS2R3900
ENSP00000247881TAS2R4900
ENSP00000247883TAS2R5900
ENSP00000248076F2RL3900
ENSP00000248996GNAZ900
ENSP00000249016MCHR1931
ENSP00000249041GALR3940
ENSP00000249284TAS2R16900
ENSP00000250615AANAT859
ENSP00000254235ADCY7908
ENSP00000254976SNAP25920
ENSP00000255008SSTR4928
ENSP00000255262NMUR2922
ENSP00000255380CHRM3908
ENSP00000256010NTS938
ENSP00000256857GRP917
ENSP00000256906HRH4935
ENSP00000257068MTNR1B914
ENSP00000257254APLNR922
ENSP00000257497ANXA1907
ENSP00000258042NMBR922
ENSP00000258400HTR2B937
ENSP00000258743IL6897
ENSP00000259607CCL21900
ENSP00000259631CCL27900
ENSP00000260402PLCB2909
ENSP00000260600ADCY3908
ENSP00000261187SLC16A7800
ENSP00000261205SYT1920
ENSP00000262158SMAD7800
ENSP00000262178VIPR2900
ENSP00000262441GLP2R900
ENSP00000262735PPARA826
ENSP00000262958GNA15919
ENSP00000263341IL1B859
ENSP00000263967PIK3CA908
ENSP00000264218NMU900
ENSP00000264708POMC994
ENSP00000264938SLC9A3800
ENSP00000265023KNG1947
ENSP00000265372CREM816
ENSP00000265572OPRK1956
ENSP00000265643GAL948
ENSP00000267017NPFF900
ENSP00000267377SSTR1928
ENSP00000267549GPR65922
ENSP00000269582PNMT993
ENSP00000270162SIK1818
ENSP00000270349SLC6A3967
ENSP00000270631PTH2900
ENSP00000271331PROK1900
ENSP00000272190REN934
ENSP00000272644GPR17900
ENSP00000272847PTH2R908
ENSP00000272928ACKR3922
ENSP00000273430AGTR1943
ENSP00000274335PIK3R1900
ENSP00000275216TAAR1988
ENSP00000276198HTR2C958
ENSP00000276373SLC18A1914
ENSP00000276414GNRH1938
ENSP00000276571CRH993
ENSP00000277942NPFFR1928
ENSP00000278175ADM919
ENSP00000279230PLCB3900
ENSP00000280155ADRA2A994
ENSP00000281806MCHR2922
ENSP00000282018CYSLTR2900
ENSP00000282091PTH915
ENSP00000282753GRM1912
ENSP00000284981APP909
ENSP00000286355ADCY8917
ENSP00000286548GNAQ926
ENSP00000286758CXCL13900
ENSP00000287641SST947
ENSP00000287820PPARG828
ENSP00000287907HTR5A929
ENSP00000289753HTR6933
ENSP00000291294PTGIR937
ENSP00000292174CXCR5900
ENSP00000292301CCR2922
ENSP00000292303CCR5984
ENSP00000292513PTGER1928
ENSP00000293272CCL5900
ENSP00000293275CCL16900
ENSP00000293330HCRT942
ENSP00000293778CXCL16900
ENSP00000293897SSTR5932
ENSP00000294016ADCY9907
ENSP00000294954LHCGR900
ENSP00000295589CCKAR922
ENSP00000295619PROK2900
ENSP00000295683CXCR1900
ENSP00000296026CXCL3900
ENSP00000296027CXCL5900
ENSP00000296028PPBP911
ENSP00000296140CCR1922
ENSP00000296641F2RL2900
ENSP00000296677F2RL1900
ENSP00000297195SLC29A4900
ENSP00000297313RGS20900
ENSP00000297323ADCY1909
ENSP00000297469GPER1926
ENSP00000297494NOS3949
ENSP00000298171TSHR900
ENSP00000298386RXFP2900
ENSP00000298440OXGR1900
ENSP00000298472SLC18A2945
ENSP00000299178AVPR1A933
ENSP00000299502SERPINB2817
ENSP00000299727GALR1943
ENSP00000299766MC4R940
ENSP00000300108TAC3915
ENSP00000301908PNOC907
ENSP00000301974PTAFR900
ENSP00000302079C3AR1900
ENSP00000302150PRL881
ENSP00000302707FPR1900
ENSP00000302811MTNR1A914
ENSP00000302846PTGER4922
ENSP00000303248RXFP1900
ENSP00000303325TACR3900
ENSP00000303424PTGDR922
ENSP00000303452TRH946
ENSP00000303522TACR1924
ENSP00000303686NTSR2922
ENSP00000303775PROKR1922
ENSP00000304414CXCR6922
ENSP00000304501ADORA2B935
ENSP00000304767P2RY1948
ENSP00000305372ADRB2997
ENSP00000305416S1PR1900
ENSP00000305464APLN907
ENSP00000305613CPLX1920
ENSP00000305651CXCL10900
ENSP00000305742LRTOMT974
ENSP00000305877NMUR1922
ENSP00000306129DRD5940
ENSP00000306138GRM5914
ENSP00000306245FOS893
ENSP00000306490CHRM1900
ENSP00000306512IL8982
ENSP00000306662ADRA1B975
ENSP00000306884CXCL11900
ENSP00000307259P2RY12909
ENSP00000307305DDIT4800
ENSP00000307445LTB4R922
ENSP00000307713BDKRB2900
ENSP00000307766HTR1E922
ENSP00000307822NPFFR2928
ENSP00000308361P2RY14900
ENSP00000308549ADORA1933
ENSP00000308815CCL19900
ENSP00000309493GPRC6A900
ENSP00000309771P2RY6908
ENSP00000309818TRHR937
ENSP00000310305P2RY2911
ENSP00000310405XCR1900
ENSP00000311032CASP3737
ENSP00000311405ADCY6909
ENSP00000312126ADCY4908
ENSP00000312262ADRBK1923
ENSP00000312999GNAI2916
ENSP00000313661HTR1D937
ENSP00000314214VAMP2900
ENSP00000314420PER1818
ENSP00000315011EDNRA966
ENSP00000316244HTR1A963
ENSP00000318077MC5R922
ENSP00000319635CXCR2900
ENSP00000319744GPR4900
ENSP00000319984CHRM2900
ENSP00000320180GHRHR900
ENSP00000320376P2RY13907
ENSP00000321106TAC1993
ENSP00000321326F2R900
ENSP00000321999PTH1R908
ENSP00000322788MMP1800
ENSP00000322924HTR1F934
ENSP00000323516UTS2R922
ENSP00000324248PENK926
ENSP00000324270OXTR950
ENSP00000326159KLK4830
ENSP00000326432CCR8900
ENSP00000327246VIPR1907
ENSP00000327251NOS2853
ENSP00000327652946
ENSP00000327724TAS2R60900
ENSP00000327875LPAR5900
ENSP00000328230FFAR3900
ENSP00000328472S1PR5900
ENSP00000328708RXFP3922
ENSP00000328818GPR132900
ENSP00000329684GALR2940
ENSP00000330070NPW900
ENSP00000330138SSTR3928
ENSP00000330284NPBWR1922
ENSP00000331358GAST914
ENSP00000331746CALCA928
ENSP00000332225PMCH915
ENSP00000332504CCR10900
ENSP00000332591NPY2R932
ENSP00000332659CCR4922
ENSP00000332766NPB900
ENSP00000332812PTGDR2900
ENSP00000333194RGS19900
ENSP00000333821MC2R929
ENSP00000334050TAS2R42900
ENSP00000334105PLCB4900
ENSP00000334448GNG2900
ENSP00000335544CCKBR922
ENSP00000335560900
ENSP00000335657CCK934
ENSP00000336630ADORA2A931
ENSP00000336764OPRL1929
ENSP00000337128EDN3920
ENSP00000337261ARHGEF1900
ENSP00000337459NOS1829
ENSP00000337949HTR7972
ENSP00000338018HIF1A800
ENSP00000338072AVPR2922
ENSP00000338185PLCB1900
ENSP00000338345SNCA734
ENSP00000339299TRIO900
ENSP00000339377NPY5R932
ENSP00000339393CCR6900
ENSP00000340191FPR2900
ENSP00000340526UTS2B900
ENSP00000340684MAOA992
ENSP00000340943CRHR2926
ENSP00000341821FPR3900
ENSP00000342560HRH3951
ENSP00000342952ADCY2940
ENSP00000343027GNAI1900
ENSP00000343428GPR18900
ENSP00000343645SULT1A3725
ENSP00000343782ADRB3997
ENSP00000344173GRM8900
ENSP00000344353LPAR6900
ENSP00000345487QRFP900
ENSP00000346017CALCB900
ENSP00000347197C5AR1900
ENSP00000348918SAA1900
ENSP00000349003PTGER3929
ENSP00000349478HCAR1900
ENSP00000350005GIP909
ENSP00000350198SSTR2928
ENSP00000350256CCR9922
ENSP00000350348GRM7907
ENSP00000350616DDC845
ENSP00000350878S1PR3900
ENSP00000351671CCL20900
ENSP00000351755LPAR1922
ENSP00000352561CALCR900
ENSP00000352839NPSR1922
ENSP00000353198PYY929
ENSP00000353915HTR4939
ENSP00000354416CCL28900
ENSP00000354511COMT953
ENSP00000354569922
ENSP00000354652NPY1R942
ENSP00000354859DRD2990
ENSP00000354901CXCL9900
ENSP00000355156SUCNR1900
ENSP00000355316GRM3909
ENSP00000355523RGS7907
ENSP00000355627AGT920
ENSP00000355920SLC22A2900
ENSP00000355930SLC22A1900
ENSP00000356162KISS1907
ENSP00000356213VIP947
ENSP00000356429RGS1900
ENSP00000356430RGS18900
ENSP00000356792XCL1900
ENSP00000356793XCL2900
ENSP00000357301RXFP4922
ENSP00000358099RGS10900
ENSP00000358301ADRB1997
ENSP00000358327CASP7700
ENSP00000358511CNR1987
ENSP00000358730ADORA3920
ENSP00000358783NPBWR2922
ENSP00000358867GNAI3900
ENSP00000358963HTR1B941
ENSP00000359532NTSR1922
ENSP00000359643LPAR3922
ENSP00000359793PTGFR922
ENSP00000359899HCRTR2922
ENSP00000360141GNAS900
ENSP00000360973AGTR2932
ENSP00000361125VEGFA830
ENSP00000361141OPN4929
ENSP00000361668EDN2900
ENSP00000362353GLP1R900
ENSP00000362398900
ENSP00000362401CYSLTR1900
ENSP00000362403TACR2900
ENSP00000362795CXCR3900
ENSP00000362810HCRTR1931
ENSP00000363296GRM4900
ENSP00000363431NPY4R922
ENSP00000363596CNR2922
ENSP00000363643P2RY4908
ENSP00000365651NPPB752
ENSP00000365807GNA14915
ENSP00000366061NMS900
ENSP00000366416EDNRB957
ENSP00000366506HRH2938
ENSP00000367309MAOB952
ENSP00000367869900
ENSP00000367930OXER1900
ENSP00000367959HTR2A998
ENSP00000368683EDN1955
ENSP00000368766ADRA1D969
ENSP00000369643GRPR922
ENSP00000369647AVP953
ENSP00000369960ADRA1A977
ENSP00000370571TH989
ENSP00000371932TAS2R1900
ENSP00000372750CHRM5900
ENSP00000373169DRD3935
ENSP00000375066HCAR2900
ENSP00000375086CCL25900
ENSP00000375091TAS2R19900
ENSP00000375093TAS2R31900
ENSP00000375095TAS2R13900
ENSP00000375893GPR55900
ENSP00000376609GRK5917
ENSP00000376776DBH998
ENSP00000377948QRFPR922
ENSP00000378089NMB900
ENSP00000378492GRM2912
ENSP00000379086ADM2900
ENSP00000379110CXCL1900
ENSP00000379140CXCL12900
ENSP00000379213PTHLH900
ENSP00000379514ADCYAP1R1900
ENSP00000380247HRH1912
ENSP00000380942ARHGEF12900
ENSP00000381105NPS957
ENSP00000381333CRHR1935
ENSP00000381339GNAT3900
ENSP00000383558GCGR900
ENSP00000384665LPAR2922
ENSP00000384708FSHR919
ENSP00000386069ADRA2C995
ENSP00000386201TAS2R41900
ENSP00000386210TAS2R40900
ENSP00000386229RGS14900
ENSP00000386884CXCR4922
ENSP00000387281ADRA2B996
ENSP00000387662GCG956
ENSP00000387699CREB1869
ENSP00000388825MLN900
ENSP00000393333TBXA2R963
ENSP00000394624OPRM1963
ENSP00000397181RGS4927
ENSP00000397297NTF3853
ENSP00000398698TNF742
ENSP00000400717GNA13900
ENSP00000405095TAS2R39900
ENSP00000408526IMPA1786
ENSP00000409378CHRM4900
ENSP00000411658ADCYAP1914
ENSP00000414303BDNF901
ENSP00000416293SLC2A1823
ENSP00000419361ADCY5909
ENSP00000420194CASR900
ENSP00000424040TAS2R50900
ENSP00000427279CXCL2900
ENSP00000428417RIMS1900
ENSP00000428824GPBAR1900
ENSP00000431719TAS2R43900
ENSP00000433290LTB4R2922
ENSP00000434045GPR68900
ENSP00000436450TAS2R46900
ENSP00000436714HCAR3900
ENSP00000441600CCR3922
ENSP00000441624TAS2R20900
ENSP00000441949TAS2R14900
ENSP00000444736TAS2R30900
ENSP00000448059PAH967
ENSP00000448219TAS2R38910
ENSP00000451030RGS6900
ENSP00000451605MC1R922
ENSP00000466933S1PR2900
ENSP00000467494GIPR900
ENSP00000468991MTRNR2L12900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.