Details of Metabolite

General Information of MET (ID: META00209)
Name Norepinephrine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-Palmitoylcarnitine; (-)-(R)-Norepinephrine; (-)-Arterenol; (-)-Noradrenaline; (-)-Norepinephrine; (-)-alpha-(Aminomethyl)protocatechuyl alcohol; (2S)-2-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}pentyl]amino}-4-phenylbutanoate; (3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate; (3R)-3-(Hexadecanoyloxy)-4-(trimethylazaniumyl)butanoic acid; (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoate; (3R)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid; (3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoate; (3S)-3-Hexadecanoyloxy-4-(trimethylammonio)butanoic acid; (3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoate; (3S)-3-Palmitoyloxy-4-(trimethylammonio)butanoic acid; (R)-(-)-Norepinephrine; (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; (R)-Noradrenaline; (R)-Norepinephrine; 2-Keto-adipate; 2-Ketoadipate; 2-Ketoadipic acid; 2-Oxoadipate; 2-Oxoadipic acid; 2-Oxohexanedioate; 2-Oxohexanedioic acid; 2-Oxohexanedionic acid; 2-oxo-Hexanedioate; 2-oxo-Hexanedioic acid; 3-Carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-1-propanaminium; 4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol; Abbott brand OF levophed bitartrate; Adrenor; Aktamin; Arterenol; Aventis brand OF norepinephrine hydrochloride; Bitartrate, levophed; Bitartrate, noradrenaline; Bitartrate, norepinephrine; D-Palmitylcarnitine; Dihydrocodehydrogenase II; Dihydronicotinamide adenine dinucleotide phosphate; Dihydronicotinamide adenine dinucleotide-p; Dihydrotriphosphopyridine nucleotide reduced; Hexadecanoyl-L-carnitine; Hexadecanoylcarnitine; Hexadecenoyl carnitine; Hydrochloride, norepinephrine; L(-)-Palmitylcarnitine; L-2-Amino-1-(3,4-dihydroxyphenyl)ethanol; L-3,4-Dihydroxyphenylethanolamine; L-Arterenol; L-Carnitine palmitoyl ester; L-NOREPINEPHRINE; L-Noradrenaline; L-Palmitoyl-L-carnitine; L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol; Levarterenol; Levoarterenol; Levonor; Levonoradrenaline; Levonorepinephrine; Levophed; NADP-reduced; Nicotinamide adenine dinucleotide phosphate - reduced; Nicotinamide-adenine-dinucleotide-phosphorate; Nicotinamide-adenine-dinucleotide-phosphoric acid; Nor adrenalin; Nor-epirenan; Noradrenalin; Noradrenaline; Noradrenaline bitartrate; Norartrinal; Norepinefrina; Norepinephrin D-tartrate (1:1); Norepinephrine D-tartrate (1:1); Norepinephrine L-tartrate (1:1); Norepinephrine L-tartrate (1:1), (+,-)-isomer; Norepinephrine L-tartrate (1:1), monohydrate; Norepinephrine L-tartrate (1:1), monohydrate, (+)-isomer; Norepinephrine L-tartrate (1:2); Norepinephrine bitartrate; Norepinephrine hydrochloride; Norepinephrine hydrochloride, (+)-isomer; Norepinephrine hydrochloride, (+,-)-isomer; Norepinephrine, (+,-)-isomer; Norepinephrinum; Norepirenamine; O-Hexadecanoyl-(R)-carnitine; O-Hexadecanoyl-R-carnitine; Oxoadipate; Palmitoyl D-carnitine; Palmitoyl-(-)-carnitine; Palmitoyl-L-carnitine; Palmitoylcarnitine; Palmityl-L-carnitine; Palmitylcarnitine; Reduced codehydrase II; Reduced coenzyme II; Reduced cozymase II; Reduced triphosphopyridine nucleotide; Renaudin brand OF norepinephrine bitartrate; Sympathin e; Triphosphopyridine nucleotide reduced; Triphosphopyridine nucleotide reduced', 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide, 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide, Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide, Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide, 'b-NADPH; a-Ketoadipate; a-Ketoadipic acid; a-Oxoadipate; a-Oxoadipic acid; alpha-Ketoadipate; alpha-Ketoadipic acid; alpha-Oxoadipate; alpha-Oxoadipic acid', 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide, 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide, Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide, Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide, 'b-NADPH; b-Nicotinamide-adenine-dinucleotide-phosphorate; b-Nicotinamide-adenine-dinucleotide-phosphoric acid; beta-NADPH; beta-Nicotinamide-adenine-dinucleotide-phosphorate; beta-Nicotinamide-adenine-dinucleotide-phosphoric acid
Source Endogenous;Food;Drug;Toxins/Pollutant;Cosmetic;TCM Ingredients
Structure Type   Benzenediols  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Phenols
Benzenediols
PubChem CID
439260
HMDB ID
HMDB0000216
Formula
C8H11NO3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00547
DrugBank ID
DB00368
ChEBI ID
18357
FooDB ID
FDB016812
ChemSpider ID
388394
METLIN ID
5226
Physicochemical Properties Molecular Weight 169.18 Topological Polar Surface Area 86.7
XlogP -1.2 Complexity 142
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Function
Norepinephrine is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas. Norepinephrine is also a microbial metabolite; urinary noradrenaline is produced by Escherichia, Bacillus, and Saccharomyces. Norepinephrine is found in alcoholic beverages, banana peels and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum), and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. Norepinephrine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Neuropeptide Y (NPY)
            Neuropeptide Y (NPY) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Antagonist ([D-Trp32]NPY) of Npy
                      Induced Change Norepinephrine concentration: increase (FC = 1.70)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that antagonist [D-Trp32]NPY of Npy leads to the increase of norepinephrine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Overexpression of Npy
                      Induced Change Norepinephrine concentration: increase (FC = 1.50)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Npy leads to the increase of norepinephrine levels compared with control group.
      Oxidoreductases (EC 1)
            Formyltetrahydrofolate dehydrogenase (ALDH1L2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Mutation of ALDH1L2
                      Induced Change Norepinephrine concentration: increase (FC = 4)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Genetic disorders of keratinisation [ICD-11: EC20]
                      Details It is reported that mutation (patients) of ALDH1L2 leads to the increase of norepinephrine levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Knockout of TP53
                      Induced Change Norepinephrine concentration: increase (Log2 FC=1.72)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of norepinephrine levels compared with control group.
References
1 Effects of neuropeptide Y (NPY) and [D-Trp32]NPY on monoamine and metabolite levels in dialysates from rat hypothalamus during feeding behavior. Neuropeptides. 1996 Aug;30(4):391-8.
2 Deleterious mutations in ALDH1L2 suggest a novel cause for neuro-ichthyotic syndrome. NPJ Genom Med. 2019 Jul 23;4:17.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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