NP-MRD: Showing NP-Card for Metanephrine (NP0087128)

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Record Information

Version

2.0

Created at

2022-05-11 16:40:54 UTC

Updated at

2022-05-11 16:40:54 UTC

NP-MRD ID

NP0087128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metanephrine

Description

Metanephrine, also known as metadrenaline, 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. Metanephrine is a very strong basic compound (based on its pKa). Within humans, metanephrine participates in a number of enzymatic reactions. In particular, metanephrine can be converted into 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, metanephrine and pyrocatechol can be biosynthesized from epinephrine and guaiacol through the action of the enzyme catechol O-methyltransferase. Metanephrine was first documented in 1979 (PMID: 434011). In humans, metanephrine is involved in the metabolic disorder called tyrosinemia type I (PMID: 7251775) (PMID: 10338428) (PMID: 12153741) (PMID: 7058845).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.8736    1.5388    0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.9099   -0.6800 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5146    1.3331   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4015   -0.1255   -0.6042 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2672   -0.9218    0.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -0.6685   -0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -2.0332   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3073   -2.6906   -0.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4378   -1.9442   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6554   -2.5764   -0.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3219   -0.5704   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4877    0.1251    0.2168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4078    1.5306    0.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0878    0.0540   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832    0.4629    0.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8027    1.9790   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8086    2.0318    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0709    1.7661   -1.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6965    1.9299   -0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3743    1.4794    0.7483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673   -0.3019   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902   -1.1315    1.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7699   -2.6680   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3714   -3.7851   -0.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7321   -3.5666   -0.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4205    1.9823    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8565    1.8362    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    1.9094   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    1.1153   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6 14  2  0
 14 11  1  0
 11 12  1  0
 12 13  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
 14 29  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 10 25  1  0
  8 24  1  0
  7 23  1  0
M  END


  Mrv0541 02231219522D          

 14 14  0  0  0  0            999 V2000
   26.0114  -11.7790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7261   -8.8914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4405  -12.6040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1550   -8.0664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.4405   -9.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1550   -8.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2969  -11.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8694   -7.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7261  -11.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4405  -11.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4405  -10.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7261  -10.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1550  -11.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1550  -10.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  9  1  0  0  0  0
  2  5  1  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCC(O)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3

> <INCHI_KEY>
JWJCTZKFYGDABJ-UHFFFAOYSA-N

> <FORMULA>
C10H15NO3

> <MOLECULAR_WEIGHT>
197.231

> <EXACT_MASS>
197.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.126091348772846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-0.0006810773060760073

> <ALOGPS_LOGS>
-1.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.2112903807181

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.051412961702267

> <JCHEM_PKA_STRONGEST_BASIC>
9.249028257921951

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
53.71260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-metanephrine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.555 -21.987   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.889 -16.597   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      51.222 -23.527   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      52.556 -15.057   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      51.222 -17.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      52.556 -16.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.221 -21.217   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      53.890 -14.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.889 -21.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      51.222 -21.987   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      51.222 -18.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.889 -19.677   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.556 -21.217   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      52.556 -19.677   0.000  0.00  0.00           C+0
CONECT    1    7    9                                                       
CONECT    2    5                                                            
CONECT    3   10                                                            
CONECT    4    6    8                                                       
CONECT    5    2    6   11                                                  
CONECT    6    4    5                                                       
CONECT    7    1                                                            
CONECT    8    4                                                            
CONECT    9    1   10   12                                                  
CONECT   10    3    9   13                                                  
CONECT   11    5   12   14                                                  
CONECT   12    9   11                                                       
CONECT   13   10   14                                                       
CONECT   14   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-metanephrine	HMDB
3-Methoxy-adrenaline	HMDB
3-Methoxyadrenaline	HMDB
3-O-Methyl-adrenaline	HMDB
3-O-Methylepinephrine	HMDB
4-Hydroxy-3-methoxy-N-methylphenethanolamine	HMDB
DL-3-O-Methyladrenaline	HMDB
DL-Metanephrine	HMDB
m-O-Methyladrenaline	HMDB
Metadrenaline	HMDB

Chemical Formula

C₁₀H₁₅NO₃

Average Mass

197.2310 Da

Monoisotopic Mass

197.10519 Da

IUPAC Name

4-[1-hydroxy-2-(methylamino)ethyl]-2-methoxyphenol

Traditional Name

(+/-)-metanephrine

CAS Registry Number

Not Available

SMILES

CNCC(O)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3

InChI Key

JWJCTZKFYGDABJ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
Secondary amine
Ether
Secondary aliphatic amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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-11877 )

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	-0.27	ALOGPS
logP	-0.00068	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.71 m³·mol⁻¹	ChemAxon
Polarizability	21.13 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

External Links

HMDB ID

HMDB0004063

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023296

KNApSAcK ID

Not Available

Chemspider ID

19844

KEGG Compound ID

C05588

BioCyc ID

Not Available

BiGG ID

46078

Wikipedia Link

Metanephrine

METLIN ID

PubChem Compound

21100

PDB ID

Not Available

ChEBI ID

144365

Good Scents ID

Not Available

References

General References

Uchikura K, Horikawa R, Tanimura T, Kabasawa Y: Determination of catecholamines by radioenzymatic assay using ion-pair liquid chromatography. J Chromatogr. 1981 Apr 10;223(1):41-50. [PubMed:7251775 ]
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 ]
van Dam PS, van Gils A, Canninga-van Dijk MR, de Koning EJ, Hofland LJ, de Herder WW: Sequential ACTH and catecholamine secretion in a phaeochromocytoma. Eur J Endocrinol. 2002 Aug;147(2):201-6. doi: 10.1530/eje.0.1470201. [PubMed:12153741 ]
Artal R, Platt LD, Kammula RK, Strassner HT, Gratacos J, Golde SH: Sympathoadrenal activity in infants of diabetic mothers. Am J Obstet Gynecol. 1982 Feb 15;142(4):436-9. doi: 10.1016/s0002-9378(16)32386-9. [PubMed:7058845 ]
Artal R, Hobel CJ, Lam R, Oddie TH, Fisher DA: Free metanephrine in human amniotic fluid as an index of fetal sympathetic nervous system maturation. Am J Obstet Gynecol. 1979 Feb 15;133(4):452-4. [PubMed:434011 ]

Showing NP-Card for Metanephrine (NP0087128)

MOL for NP0087128 (Metanephrine)

3D MOL for NP0087128 (Metanephrine)

3D SDF for NP0087128 (Metanephrine)

3D-SDF for NP0087128 (Metanephrine)

PDB for NP0087128 (Metanephrine)

3D PDB for NP0087128 (Metanephrine)

SMILES for NP0087128 (Metanephrine)

INCHI for NP0087128 (Metanephrine)

Structure for NP0087128 (Metanephrine)

3D Structure for NP0087128 (Metanephrine)