| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:26:52 UTC |
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| Update Date | 2020-05-21 16:28:46 UTC |
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| BMDB ID | BMDB0000216 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Norepinephrine |
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| Description | Norepinephrine, 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (-)-Arterenol | ChEBI | | (-)-Noradrenaline | ChEBI | | (-)-Norepinephrine | ChEBI | | (R)-(-)-Norepinephrine | ChEBI | | (R)-4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol | ChEBI | | (R)-Norepinephrine | ChEBI | | 4-[(1R)-2-amino-1-Hydroxyethyl]-1,2-benzenediol | ChEBI | | Arterenol | ChEBI | | L-Noradrenaline | ChEBI | | L-Norepinephrine | ChEBI | | Noradrenaline | ChEBI | | Norepinefrina | ChEBI | | Norepinephrinum | ChEBI | | (-)-(R)-Norepinephrine | HMDB | | (-)-alpha-(Aminomethyl)protocatechuyl alcohol | HMDB | | (R)-Noradrenaline | HMDB | | 4-(2-amino-1-Hydroxyethyl)-1,2-benzenediol | HMDB | | Adrenor | HMDB | | Aktamin | HMDB | | L-2-amino-1-(3,4-Dihydroxyphenyl)ethanol | HMDB | | L-3,4-Dihydroxyphenylethanolamine | HMDB | | L-alpha-(Aminomethyl)-3,4-dihydroxybenzyl alcohol | HMDB | | L-Arterenol | HMDB | | Levarterenol | HMDB, MeSH | | Levoarterenol | HMDB | | Levonor | HMDB, MeSH | | Levonoradrenaline | HMDB | | Levonorepinephrine | HMDB, MeSH | | Levophed | HMDB, MeSH | | Nor-epirenan | HMDB | | Noradrenalin | HMDB | | Norartrinal | HMDB | | Norepirenamine | HMDB | | Sympathin E | HMDB |
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| Chemical Formula | C8H11NO3 |
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| Average Molecular Weight | 169.1778 |
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| Monoisotopic Molecular Weight | 169.073893223 |
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| IUPAC Name | 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol |
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| Traditional Name | norepinephrine |
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| CAS Registry Number | 51-41-2 |
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| SMILES | NC[C@H](O)C1=CC(O)=C(O)C=C1 |
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| 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 |
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| InChI Key | SFLSHLFXELFNJZ-QMMMGPOBSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenols |
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| Sub Class | Benzenediols |
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| Direct Parent | Catechols |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected but not Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 145.2 - 146.4 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 849 mg/mL | Not Available | | LogP | -1.24 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Adrenal Medulla
- Bladder
- Brain
- Epidermis
- Fibroblasts
- Heart
- Intestine
- Kidney
- Leukocyte
- Liver
- Milk
- Neuron
- Ovary
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Skeletal Muscle
- Testis
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| Pathways | |
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| Normal Concentrations |
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| Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Gland | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Adrenal Medulla | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Heart | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Leukocyte | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ovary | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Skeletal Muscle | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000216 |
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| DrugBank ID | DB00368 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB016812 |
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| KNApSAcK ID | C00001424 |
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| Chemspider ID | 388394 |
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| KEGG Compound ID | C00547 |
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| BioCyc ID | Not Available |
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| BiGG ID | 35313 |
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| Wikipedia Link | Norepinephrine |
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| METLIN ID | 5226 |
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| PubChem Compound | 439260 |
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| PDB ID | Not Available |
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| ChEBI ID | 18357 |
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| References |
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| Synthesis Reference | Goodall, McC.; Kirshner, Norman. Biosynthesis of adrenaline and norepinephrine by sympathetic nerves and ganglia. Circulation (1958), 17 366-71. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
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