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:
norepinephrine (ne), neopinephrine (noradrenaline), noradrenaline, norepinephrine (noradrenaline), l-noradrenaline, norepinephrine
External chemical identifiers:
CID:CID_439260; ChEMBL:CHEMBL1437; ChEBI: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
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 0.472427


Norepinephrine
ADME 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
Number of Brenk structural alerts SwissADME 1
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
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_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000578ENSG00000121853GHSR2693ChEMBL
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000627ENSG00000102539MLNR2862ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000727ENSG00000178394HTR1A3350ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000735ENSG00000166736HTR3A3359ChEMBL
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328ChEMBL, NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL
TAR_EXP_000330ENSG00000144891AGTR1185ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000116ENSG00000010322NISCH11188ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000125ENSG00000101180HRH311255ChEMBL
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000144ENSG00000101204CHRNA41137ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL, NPASS
TAR_EXP_000236ENSG00000170214ADRA1B147ChEMBL, NPASS
TAR_EXP_000239ENSG00000120907ADRA1A148BindingDB, ChEMBL, NPASS
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL, NPASS
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL, NPASS
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL, NPASS
TAR_EXP_000258ENSG00000043591ADRB1153BindingDB, ChEMBL
TAR_EXP_000261ENSG00000169252ADRB2154BindingDB, ChEMBL, NPASS
TAR_EXP_000267ENSG00000188778ADRB3155BindingDB, ChEMBL, NPASS
TAR_EXP_000289ENSG00000110887DAO1610BindingDB, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL, NPASS
TAR_EXP_000325ENSG00000149295DRD21813BindingDB, ChEMBL, NPASS
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000367ENSG00000112759SLC29A12030ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001053ENSG00000172572PDE3A5139ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001061ENSG00000113448PDE4D5144ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001190ENSG00000126895AVPR2554ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL, NPASS
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_001539ENSG00000146477SLC22A36581ChEMBL, NPASS
TAR_EXP_001540ENSG00000112499SLC22A26582ChEMBL, NPASS
TAR_EXP_001591ENSG00000006638TBXA2R6915ChEMBL
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_001808ENSG00000276582ABCB118647NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000902ENSG00000213648SULT1A4445329ChEMBL
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000860ENSG00000152601MBNL14154ChEMBL, NPASS