NP-MRD: Showing NP-Card for noradrenaline (NP0244426)

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Record Information

Version

2.0

Created at

2022-09-07 05:13:30 UTC

Updated at

2022-09-07 05:13:30 UTC

NP-MRD ID

NP0244426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

noradrenaline

Description

Xi-Norepinephrine, also known as noradrenalina, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Xi-Norepinephrine is a very strong basic compound (based on its pKa). Outside of the human body, xi-Norepinephrine has been detected, but not quantified in, several different foods, such as alcoholic beverages, citrus, fruits, green vegetables, and potato. This could make XI-norepinephrine a potential biomarker for the consumption of these foods. noradrenaline is found in Homo sapiens, Mus musculus and Portulaca oleracea. A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    8    9                                                       
CONECT    5    1    3    8                                                  
CONECT    6    2    7   10                                                  
CONECT    7    3    6   11                                                  
CONECT    8    4    5   12                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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Synonyms

Value	Source
Noradrenalina	ChEBI
Norepinephrine	ChEBI
Bitartrate, norepinephrine	MeSH
Levarterenol	MeSH
Noradrenaline bitartrate	MeSH
Norepinephrin D-tartrate (1:1)	MeSH
Norepinephrine L-tartrate (1:1), monohydrate, (+)-isomer	MeSH
Norepinephrine, (+,-)-isomer	MeSH
Hydrochloride, norepinephrine	MeSH
Levonorepinephrine	MeSH
Levophed	MeSH
Levophed bitartrate	MeSH
Noradrenaline	MeSH
Noradrénaline tartrate renaudin	MeSH
Norepinephrine D-tartrate (1:1)	MeSH
Norepinephrine L-tartrate (1:1), monohydrate	MeSH
Norepinephrine L-tartrate, (+)-isomer	MeSH
Tartrate renaudin, noradrénaline	MeSH
Abbott brand OF levophed bitartrate	MeSH
Arterenol	MeSH
Aventis brand OF norepinephrine hydrochloride	MeSH
Bitartrate, levophed	MeSH
Norepinephrine bitartrate	MeSH
Norepinephrine hydrochloride	MeSH
Norepinephrine L-tartrate (1:1), (+,-)-isomer	MeSH
Renaudin, noradrénaline tartrate	MeSH
Bitartrate, noradrenaline	MeSH
Levonor	MeSH
Norepinephrine hydrochloride, (+)-isomer	MeSH
Norepinephrine hydrochloride, (+,-)-isomer	MeSH
Norepinephrine L-tartrate (1:1)	MeSH
Norepinephrine L-tartrate (1:2)	MeSH
Norepinephrine, (+)-isomer	MeSH
Renaudin brand OF norepinephrine bitartrate	MeSH

Chemical Formula

C₈H₁₁NO₃

Average Mass

169.1778 Da

Monoisotopic Mass

169.07389 Da

IUPAC Name

4-(2-amino-1-hydroxyethyl)benzene-1,2-diol

Traditional Name

noradrenaline

CAS Registry Number

Not Available

SMILES

NCC(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

InChI Key

SFLSHLFXELFNJZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

catecholamine (CHEBI:33569 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-0.68	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	8.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.46 m³·mol⁻¹	ChemAxon
Polarizability	16.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037685

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016812

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

951

PDB ID

Not Available

ChEBI ID

33569

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for noradrenaline (NP0244426)

MOL for NP0244426 (noradrenaline)

3D MOL for NP0244426 (noradrenaline)

3D SDF for NP0244426 (noradrenaline)

3D-SDF for NP0244426 (noradrenaline)

PDB for NP0244426 (noradrenaline)

3D PDB for NP0244426 (noradrenaline)

SMILES for NP0244426 (noradrenaline)

INCHI for NP0244426 (noradrenaline)

Structure for NP0244426 (noradrenaline)

3D Structure for NP0244426 (noradrenaline)