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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:12 UTC

HMDB ID

HMDB0000819

Secondary Accession Numbers

HMDB00819

Metabolite Identification

Common Name

Normetanephrine

Description

Normetanephrine, also known as normetadrenaline or N111, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Normetanephrine is a solid that is soluble in water. Normetanephrine is a metabolite of norepinephrine created by action of catechol-O-methyl transferase on norepinephrine. Within humans, normetanephrine participates in a number of enzymatic reactions. In particular, normetanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] A. It is also involved in the metabolic disorder called transient tyrosinemia of the newborn. This compound is excreted in the urine and is found in certain tissues. It is a marker for catecholamine-secreting tumors such as pheochromocytoma (PMID: 30538672 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Normetanephrine.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -1.334   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.667   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.001  -1.540   0.000  0.00  0.00           N+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8    1   12                                                  
CONECT    8    7                                                            
CONECT    9   10    3                                                       
CONECT   10    9                                                            
CONECT   11    4                                                            
CONECT   12   13    7                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+/-)-normetanephrine	HMDB
(+/-)-alpha-(aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol	HMDB
3-Methoxy-noradrenaline	HMDB
3-O-Methyl-noradrenaline	HMDB
4-(2-Amino-1-hydroxyethyl)-2-methoxyphenol	HMDB
alpha-(Aminomethyl)-4-hydroxy-3-methoxy-benzenemethanol	HMDB
DL-N-Normetanephrine	HMDB
DL-Normetanephrine	HMDB
L-Normetanephrine	HMDB
m-O-Methylnorepinephrine	HMDB
N111	HMDB
Normetadrenaline	HMDB
O-Methylnoradrenaline	HMDB
3 Methoxynoradrenaline	HMDB
3-Methoxynoradrenaline	HMDB

Chemical Formula

C₉H₁₃NO₃

Average Molecular Weight

183.2044

Monoisotopic Molecular Weight

183.089543287

IUPAC Name

4-(2-amino-1-hydroxyethyl)-2-methoxyphenol

Traditional Name

(+/-)-normetanephrine

CAS Registry Number

97-31-4

SMILES

COC1=CC(=CC=C1O)C(O)CN

InChI Identifier

InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3

InChI Key

YNYAYWLBAHXHLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
Secondary alcohol
1,2-aminoalcohol
Ether
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a guaiacol (CPD-11875 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Psychoactive substance abuse disorder

Stimulant psychosis (HMDB: HMDB0000819)

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000819)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000819)
Cerebrospinal fluid (HMDB: HMDB0000819)
Cerebrospinal Fluid (CSF) (PMID: 4073504)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0000819)
Urine (HMDB: HMDB0000819)

Organ

Brain (HMDB: HMDB0000819)

Gland

Adrenal Gland (HMDB: HMDB0000819)
Adrenal Gland (HMDB: HMDB0000819)

Cell

Hematocyte

Platelet (HMDB: HMDB0000819)

Organ substructure

Adrenal medulla (HMDB: HMDB0000819)

Source

Endogenous

Endogenous (HMDB: HMDB0000819)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (HMDB: HMDB0000819)
Tyrosine Metabolism (HMDB: HMDB0000819)

Disease pathway

Alkaptonuria (PathBank: SMP0000169)
Hawkinsinuria (PathBank: SMP0000190)
Tyrosinemia Type I (PathBank: SMP0000218)
Tyrosinemia, Transient, of the Newborn (PathBank: SMP0000494)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0000498)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0000533)

Drug action pathway

Disulfiram Action Pathway (PathBank: SMP0000429)
Disulfiram Action Pathway (HMDB: HMDB0000819)

Role

Industrial application

Pharmaceutical industry

Biomarker

Hypertension (MarkerDB: MDB00000260)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.05	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.44 g/L	ALOGPS
logP	-0.71	ALOGPS
logP	-0.39	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.71 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.94 m³·mol⁻¹	ChemAxon
Polarizability	19.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.34	31661259
DarkChem	[M-H]-	136.962	31661259
AllCCS	[M+H]+	141.55	32859911
AllCCS	[M-H]-	139.649	32859911
DeepCCS	[M+H]+	138.067	30932474
DeepCCS	[M-H]-	135.575	30932474
DeepCCS	[M-2H]-	171.186	30932474
DeepCCS	[M+Na]+	146.437	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.3	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Normetanephrine	COC1=CC(=CC=C1O)C(O)CN	2905.2	Standard polar	33892256
Normetanephrine	COC1=CC(=CC=C1O)C(O)CN	1732.8	Standard non polar	33892256
Normetanephrine	COC1=CC(=CC=C1O)C(O)CN	1716.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Normetanephrine,1TMS,isomer #1	COC1=CC(C(O)CN)=CC=C1O[Si](C)(C)C	1829.6	Semi standard non polar	33892256
Normetanephrine,1TMS,isomer #2	COC1=CC(C(CN)O[Si](C)(C)C)=CC=C1O	1749.6	Semi standard non polar	33892256
Normetanephrine,1TMS,isomer #3	COC1=CC(C(O)CN[Si](C)(C)C)=CC=C1O	1913.0	Semi standard non polar	33892256
Normetanephrine,2TMS,isomer #1	COC1=CC(C(CN)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1769.9	Semi standard non polar	33892256
Normetanephrine,2TMS,isomer #2	COC1=CC(C(O)CN[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1889.9	Semi standard non polar	33892256
Normetanephrine,2TMS,isomer #3	COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	1818.7	Semi standard non polar	33892256
Normetanephrine,2TMS,isomer #4	COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2055.9	Semi standard non polar	33892256
Normetanephrine,3TMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1806.7	Semi standard non polar	33892256
Normetanephrine,3TMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1928.6	Standard non polar	33892256
Normetanephrine,3TMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2102.6	Standard polar	33892256
Normetanephrine,3TMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2060.8	Semi standard non polar	33892256
Normetanephrine,3TMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2092.4	Standard non polar	33892256
Normetanephrine,3TMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2295.0	Standard polar	33892256
Normetanephrine,3TMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2045.1	Semi standard non polar	33892256
Normetanephrine,3TMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2148.0	Standard non polar	33892256
Normetanephrine,3TMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	2262.5	Standard polar	33892256
Normetanephrine,4TMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2094.8	Semi standard non polar	33892256
Normetanephrine,4TMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2068.0	Standard non polar	33892256
Normetanephrine,4TMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2074.0	Standard polar	33892256
Normetanephrine,1TBDMS,isomer #1	COC1=CC(C(O)CN)=CC=C1O[Si](C)(C)C(C)(C)C	2061.9	Semi standard non polar	33892256
Normetanephrine,1TBDMS,isomer #2	COC1=CC(C(CN)O[Si](C)(C)C(C)(C)C)=CC=C1O	2021.1	Semi standard non polar	33892256
Normetanephrine,1TBDMS,isomer #3	COC1=CC(C(O)CN[Si](C)(C)C(C)(C)C)=CC=C1O	2164.5	Semi standard non polar	33892256
Normetanephrine,2TBDMS,isomer #1	COC1=CC(C(CN)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2264.0	Semi standard non polar	33892256
Normetanephrine,2TBDMS,isomer #2	COC1=CC(C(O)CN[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2376.4	Semi standard non polar	33892256
Normetanephrine,2TBDMS,isomer #3	COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2316.7	Semi standard non polar	33892256
Normetanephrine,2TBDMS,isomer #4	COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	2500.1	Semi standard non polar	33892256
Normetanephrine,3TBDMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2527.4	Semi standard non polar	33892256
Normetanephrine,3TBDMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2550.6	Standard non polar	33892256
Normetanephrine,3TBDMS,isomer #1	COC1=CC(C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2482.3	Standard polar	33892256
Normetanephrine,3TBDMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2763.3	Semi standard non polar	33892256
Normetanephrine,3TBDMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2712.9	Standard non polar	33892256
Normetanephrine,3TBDMS,isomer #2	COC1=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2587.1	Standard polar	33892256
Normetanephrine,3TBDMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2702.8	Semi standard non polar	33892256
Normetanephrine,3TBDMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2736.7	Standard non polar	33892256
Normetanephrine,3TBDMS,isomer #3	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2550.9	Standard polar	33892256
Normetanephrine,4TBDMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2941.6	Semi standard non polar	33892256
Normetanephrine,4TBDMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2813.2	Standard non polar	33892256
Normetanephrine,4TBDMS,isomer #1	COC1=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2510.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Normetanephrine GC-MS (4 TMS)	splash10-00di-2920000000-906a2c3ec3c929834c7b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized)	splash10-00di-2920000000-906a2c3ec3c929834c7b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-df1660d54bc99d55b9bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (2 TMS) - 70eV, Positive	splash10-00di-1900000000-f8b939907bf23331b83f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Normetanephrine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-0900000000-cb28fbf84eae6ad4628e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05e9-4900000000-65aa73bd819270237f34	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-004i-9200000000-de463de74a0d6a9bfdb1	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOF	splash10-004i-9200000000-efafce5afe4a7c15067b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOF	splash10-05ai-1900000000-93cae41cf9bbc8fb06fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOF	splash10-014i-0900000000-4f226dd2298708c36b4d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 35V, Positive-QTOF	splash10-0h3s-5900000000-7420f0a05449387c69eb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOF	splash10-014i-0900000000-fa66b6a75bb70a6e11cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOF	splash10-05ai-1900000000-7eaa1d030beaeae5118f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOF	splash10-0002-0900000000-c2a7cb2d1889ec69b26a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOF	splash10-004i-9300000000-98a0488cc1211d99fa57	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 10V, Negative-QTOF	splash10-0002-0900000000-9997c3e9112e4558aa63	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 20V, Negative-QTOF	splash10-006t-0900000000-bd5a22c7a438d15be4bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 40V, Negative-QTOF	splash10-00dl-7900000000-863bf83793f05b65058a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOF	splash10-0002-0900000000-2a2538378e0bbcaed15f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Normetanephrine 35V, Negative-QTOF	splash10-0002-0900000000-4414d75b49a2cc82bdb6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOF	splash10-0159-0900000000-b19888f59670d542cc35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOF	splash10-014j-0900000000-26872ea42b5102a407ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOF	splash10-0fdt-4900000000-2416e3adcd40b107923d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 10V, Negative-QTOF	splash10-001i-0900000000-f95a5de2b99b6807a9ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 20V, Negative-QTOF	splash10-0gx0-0900000000-e2ba422610b39356fe57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 40V, Negative-QTOF	splash10-0ab9-3900000000-f9f0aaa8b3c0fcfee29a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 10V, Positive-QTOF	splash10-001i-0900000000-ec4dd90d9b4a388fca9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 20V, Positive-QTOF	splash10-001i-2900000000-f0ee1c53996f65eaa5cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Normetanephrine 40V, Positive-QTOF	splash10-0zgi-9300000000-91b1e27073d44d8f5025	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Adrenal Gland
Adrenal Medulla
Brain
Platelet

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00035 +/- 0.00016 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.00022 +/- 0.00052 uM	Adult (>18 years old)	Both	Normal	8878306	details
Blood	Detected and Quantified	0.00045 +/- 0.00120 uM	Adult (>18 years old)	Both	Normal	8878306	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0052 uM	Not Specified	Not Specified	Normal	4073504	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Urine	Detected and Quantified	0.85 +/- 3.17 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	0.00085 +/- 0.00317 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	2026685 12649306 9626157 12383482 15718487 10369850 11936531 3093120 7778821 978-0-911910-19-3	details
Urine	Detected and Quantified	<0.322 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	978-0-911910-19-3	details
Urine	Detected and Quantified	0.0340-0.182 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	0.00100-0.0180 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	0.0920-0.824 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	9686366	details
Urine	Detected and Quantified	0.062 +/- 0.037 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000846 +/- 0.00037 uM	Not Specified	Not Specified	Alcohol abstinence	3561163	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000185 +/- 0.00004424 uM	Not Specified	Not Specified	pheochromocytoma	7076810	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00004533 +/- 0.00001256 uM	Not Specified	Not Specified	Primary hypertension	7076810	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Both	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Urine	Detected and Quantified	0.392-0.666 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details
Urine	Detected and Quantified	0.0520-0.0780 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details
Urine	Detected and Quantified	0.016 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	0.055 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details

Associated Disorders and Diseases

Disease References

Pheochromocytoma
Foti A, Adachi M, DeQuattro V: The relationships of free to conjugated normetanephrine in plasma and spinal fluid of hypertensive patients. J Clin Endocrinol Metab. 1982 Jul;55(1):81-5. [PubMed:7076810 ]
Essential hypertension
Foti A, Adachi M, DeQuattro V: The relationships of free to conjugated normetanephrine in plasma and spinal fluid of hypertensive patients. J Clin Endocrinol Metab. 1982 Jul;55(1):81-5. [PubMed:7076810 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Aromatic L-amino acid decarboxylase deficiency
Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Brunner Syndrome
Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]

Associated OMIM IDs

171300 (Pheochromocytoma)
266600 (Crohn's disease)
608643 (Aromatic L-amino acid decarboxylase deficiency)
300615 (Brunner Syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

46080

Wikipedia Link

Normetanephrine

METLIN ID

PubChem Compound

1237

PDB ID

Not Available

ChEBI ID

144308

Food Biomarker Ontology

Not Available

VMH ID

NORMETE_L

MarkerDB ID

MDB00000260

Good Scents ID

Not Available

References

Synthesis Reference

Sejbal, Jan; Krecek, Vaclav. Method of preparing normetanephrine. Czech. (1992), 4 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. [PubMed:9626157 ]
Wester P, Bergstrom U, Eriksson A, Gezelius C, Hardy J, Winblad B: Ventricular cerebrospinal fluid monoamine transmitter and metabolite concentrations reflect human brain neurochemistry in autopsy cases. J Neurochem. 1990 Apr;54(4):1148-56. [PubMed:1968956 ]
Schmidt J, Mohr VD, Metzger P, Zirngibl H: Posttraumatic hypertension secondary to adrenal hemorrhage mimicking pheochromocytoma: case report. J Trauma. 1999 May;46(5):973-5. [PubMed:10338428 ]
Eisenhofer G, Huysmans F, Pacak K, Walther MM, Sweep FC, Lenders JW: Plasma metanephrines in renal failure. Kidney Int. 2005 Feb;67(2):668-77. [PubMed:15673315 ]
Orsulak PJ, Kizuka P, Grab E, Schildkraut JJ: Determination of urinary normetanephrine and metanephrine by radial-compression liquid chromatography and electrochemical detection. Clin Chem. 1983 Feb;29(2):305-9. [PubMed:6821934 ]
Linos DA: Management approaches to adrenal incidentalomas (adrenalomas). A view from Athens, Greece. Endocrinol Metab Clin North Am. 2000 Mar;29(1):141-57. [PubMed:10732269 ]
Oishi S, Sasaki M, Sato T, Isogai M: Coexistence of MEN 2A and papillary thyroid carcinoma and a recurrent pheochromocytoma 23 years after surgery: report of a case and a review of the Japanese literature. Jpn J Clin Oncol. 1995 Aug;25(4):153-8. [PubMed:7666591 ]
Filaire E, Legrand B, Bret K, Sagnol M, Cottet-Emard JM, Pequignot JM: Psychobiologic responses to 4 days of increased training and recovery in cyclists. Int J Sports Med. 2002 Nov;23(8):588-94. [PubMed:12439775 ]
Filaire E, Legrand B, Lac G, Pequignot JM: Training of elite cyclists: effects on mood state and selected hormonal responses. J Sports Sci. 2004 Nov-Dec;22(11-12):1025-33. [PubMed:15801496 ]
Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103. [PubMed:3035087 ]
Eisenhofer G, Goldstein DS, Sullivan P, Csako G, Brouwers FM, Lai EW, Adams KT, Pacak K: Biochemical and clinical manifestations of dopamine-producing paragangliomas: utility of plasma methoxytyramine. J Clin Endocrinol Metab. 2005 Apr;90(4):2068-75. Epub 2005 Jan 11. [PubMed:15644397 ]
Pacak K, Ilias I, Adams KT, Eisenhofer G: Biochemical diagnosis, localization and management of pheochromocytoma: focus on multiple endocrine neoplasia type 2 in relation to other hereditary syndromes and sporadic forms of the tumour. J Intern Med. 2005 Jan;257(1):60-8. [PubMed:15606377 ]
Guller U, Turek J, Eubanks S, Delong ER, Oertli D, Feldman JM: Detecting pheochromocytoma: defining the most sensitive test. Ann Surg. 2006 Jan;243(1):102-7. [PubMed:16371743 ]
Eisenhofer G, Lenders JW, Goldstein DS, Mannelli M, Csako G, Walther MM, Brouwers FM, Pacak K: Pheochromocytoma catecholamine phenotypes and prediction of tumor size and location by use of plasma free metanephrines. Clin Chem. 2005 Apr;51(4):735-44. Epub 2005 Feb 17. [PubMed:15718487 ]
Alrezk R, Suarez A, Tena I, Pacak K: Update of Pheochromocytoma Syndromes: Genetics, Biochemical Evaluation, and Imaging. Front Endocrinol (Lausanne). 2018 Nov 27;9:515. doi: 10.3389/fendo.2018.00515. eCollection 2018. [PubMed:30538672 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Normetanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Ammonia + Hydrogen peroxide	details

Enzyme Details

3. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Normetanephrine	details

Showing metabocard for Normetanephrine (HMDB0000819)

MOL for HMDB0000819 (Normetanephrine)

3D MOL for HMDB0000819 (Normetanephrine)

3D SDF for HMDB0000819 (Normetanephrine)

3D-SDF for HMDB0000819 (Normetanephrine)

PDB for HMDB0000819 (Normetanephrine)

3D PDB for HMDB0000819 (Normetanephrine)

SMILES for HMDB0000819 (Normetanephrine)

INCHI for HMDB0000819 (Normetanephrine)

Structure for HMDB0000819 (Normetanephrine)

3D Structure for HMDB0000819 (Normetanephrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions