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Record Information
Version1.0
Creation Date2016-09-30 22:26:52 UTC
Update Date2020-05-21 16:28:46 UTC
MCDB ID BMDB0000216
Secondary Accession Numbers
  • BMDB00216
Metabolite Identification
Common NameNorepinephrine
DescriptionNorepinephrine, also known as noradrenaline or arterenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Norepinephrine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Norepinephrine exists in all living organisms, ranging from bacteria to humans. Norepinephrine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(-)-ArterenolChEBI
(-)-NoradrenalineChEBI
(-)-NorepinephrineChEBI
(R)-(-)-NorepinephrineChEBI
(R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolChEBI
(R)-NorepinephrineChEBI
4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediolChEBI
ArterenolChEBI
L-NoradrenalineChEBI
L-NOREPINEPHRINEChEBI
NoradrenalineChEBI
NorepinefrinaChEBI
NorepinephrinumChEBI
Nor adrenalinKegg
(-)-(R)-NorepinephrineHMDB
(-)-alpha-(Aminomethyl)protocatechuyl alcoholHMDB
(R)-NoradrenalineHMDB
4-(2-Amino-1-hydroxyethyl)-1,2-benzenediolHMDB
AdrenorHMDB
AktaminHMDB
L-2-Amino-1-(3,4-dihydroxyphenyl)ethanolHMDB
L-3,4-DihydroxyphenylethanolamineHMDB
L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcoholHMDB
L-ArterenolHMDB
LevarterenolHMDB
LevoarterenolHMDB
LevonorHMDB
LevonoradrenalineHMDB
LevonorepinephrineHMDB
LevophedHMDB
Nor-epirenanHMDB
NoradrenalinHMDB
NorartrinalHMDB
NorepirenamineHMDB
Sympathin eHMDB
Hydrochloride, norepinephrineHMDB
Levophed bitartrateHMDB
Noradrénaline tartrate renaudinHMDB
Norepinephrine hydrochloride, (+)-isomerHMDB
Norepinephrine hydrochloride, (+,-)-isomerHMDB
Norepinephrine L-tartrate (1:1), monohydrateHMDB
Norepinephrine, (+,-)-isomerHMDB
Renaudin brand OF norepinephrine bitartrateHMDB
Bitartrate, noradrenalineHMDB
Noradrenaline bitartrateHMDB
Norepinephrine L-tartrate (1:1)HMDB
Norepinephrine L-tartrate (1:1), (+,-)-isomerHMDB
Norepinephrine L-tartrate (1:1), monohydrate, (+)-isomerHMDB
Abbott brand OF levophed bitartrateHMDB
Aventis brand OF norepinephrine hydrochlorideHMDB
Bitartrate, norepinephrineHMDB
Norepinephrin D-tartrate (1:1)HMDB
Norepinephrine bitartrateHMDB
Norepinephrine hydrochlorideHMDB
Norepinephrine D-tartrate (1:1)HMDB
Norepinephrine L-tartrate, (+)-isomerHMDB
Tartrate renaudin, noradrénalineHMDB
Bitartrate, levophedHMDB
Norepinephrine L-tartrate (1:2)HMDB
Norepinephrine, (+)-isomerHMDB
Renaudin, noradrénaline tartrateHMDB
(2S)-2-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}pentyl]amino}-4-phenylbutanoateHMDB
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoateHMDB
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoateHMDB
Hexadecanoyl-L-carnitineHMDB
HexadecanoylcarnitineHMDB
Hexadecenoyl carnitineHMDB
L-Carnitine palmitoyl esterHMDB
O-Hexadecanoyl-(R)-carnitineHMDB
O-Hexadecanoyl-R-carnitineHMDB
Palmitoyl-L-carnitineHMDB
PalmitoylcarnitineHMDB
(3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acidHMDB
(3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acidHMDB
(+)-PalmitoylcarnitineHMDB
(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoateHMDB
(3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoic acidHMDB
(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoateHMDB
(3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acidHMDB
3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminiumHMDB
D-PalmitylcarnitineHMDB
L(-)-PalmitylcarnitineHMDB
L-Palmitoyl-L-carnitineHMDB
Palmitoyl D-carnitineHMDB
Palmitoyl-(-)-carnitineHMDB
Palmityl-L-carnitineHMDB
PalmitylcarnitineHMDB
2-OxoadipateHMDB
2-Oxoadipic acidHMDB
OxoadipateHMDB
2-Keto-adipateHMDB
2-KetoadipateHMDB
2-Ketoadipic acidHMDB
2-oxo-HexanedioateHMDB
2-oxo-Hexanedioic acidHMDB
2-OxohexanedioateHMDB
2-Oxohexanedioic acidHMDB
2-Oxohexanedionic acidHMDB
a-KetoadipateHMDB
a-Ketoadipic acidHMDB
a-OxoadipateHMDB
a-Oxoadipic acidHMDB
alpha-KetoadipateHMDB
alpha-Ketoadipic acidHMDB
alpha-OxoadipateHMDB
alpha-Oxoadipic acidHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
b-NADPHHMDB
b-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-NADPHHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Dihydrocodehydrogenase IIHMDB
Dihydronicotinamide adenine dinucleotide phosphateHMDB
Dihydronicotinamide adenine dinucleotide-pHMDB
Dihydrotriphosphopyridine nucleotide reducedHMDB
NADP-reducedHMDB
Nicotinamide adenine dinucleotide phosphate - reducedHMDB
Nicotinamide-adenine-dinucleotide-phosphorateHMDB
Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Reduced codehydrase IIHMDB
Reduced coenzyme IIHMDB
Reduced cozymase IIHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide reducedHMDB
Chemical FormulaC8H11NO3
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
IUPAC Name4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
Traditional Namenorepinephrine
CAS Registry Number51-41-2
SMILES
NC[C@H](O)C1=CC(O)=C(O)C=C1
InChI Identifier
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
InChI KeySFLSHLFXELFNJZ-QMMMGPOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Organic nitrogen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145.2 - 146.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility849 mg/mLNot Available
LogP-1.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-0.68ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.46 m³·mol⁻¹ChemAxon
Polarizability16.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000216
DrugBank IDDB00368
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016812
KNApSAcK IDC00001424
Chemspider ID388394
KEGG Compound IDC00547
BioCyc IDNot Available
BiGG ID35313
Wikipedia LinkNorepinephrine
METLIN ID5226
PubChem Compound439260
PDB IDNot Available
ChEBI ID18357
References
Synthesis ReferenceGoodall, McC.; Kirshner, Norman. Biosynthesis of adrenaline and norepinephrine by sympathetic nerves and ganglia. Circulation (1958), 17 366-71.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]