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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:38:29 UTC

Update Date

2023-02-21 17:23:43 UTC

HMDB ID

HMDB0033868

Secondary Accession Numbers

HMDB33868

Metabolite Identification

Common Name

beta-O-Methylynephrine

Description

beta-O-Methylynephrine belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). beta-O-Methylynephrine has been detected, but not quantified in, citrus. This could make beta-O-methylynephrine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on beta-O-Methylynephrine.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   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      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   13                                                            
CONECT    3    5    8                                                       
CONECT    4    6    8                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   11                                                       
CONECT    8    3    4   10                                                  
CONECT    9    5    6   12                                                  
CONECT   10    7    8   13                                                  
CONECT   11    1    7                                                       
CONECT   12    9                                                            
CONECT   13    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0033868
HETATM    1  C1  UNL     1      -1.527  -2.119  -0.315  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.381  -1.016  -0.476  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.894   0.217  -0.944  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.986   0.992  -0.033  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.618   2.196  -0.651  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.808   3.301   0.131  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.313   0.254   0.109  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.100   0.148  -1.042  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.326  -0.487  -1.012  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.740  -1.009   0.190  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.964  -1.650   0.242  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.984  -0.918   1.338  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.758  -0.278   1.288  1.00  0.00           C  
HETATM   14  H1  UNL     1      -0.636  -2.140  -0.957  1.00  0.00           H  
HETATM   15  H2  UNL     1      -1.195  -2.278   0.747  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.084  -3.072  -0.539  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.318  -1.033  -0.088  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.709   0.916  -1.270  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.366   0.002  -1.931  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.378   1.160   0.981  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.219   3.273   1.084  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.378   4.165  -0.450  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.839   3.557   0.367  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.739   0.569  -1.960  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.967  -0.596  -1.866  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.982  -2.637   0.061  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.333  -1.335   2.269  1.00  0.00           H  
HETATM   28  H15 UNL     1       0.130  -0.182   2.164  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5    7   20
CONECT    5    6
CONECT    6   21   22   23
CONECT    7    8    8   13
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   12
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
b-O-Methylynephrine	Generator
Β-O-methylynephrine	Generator
b-O-Methylsynephrine	HMDB

Chemical Formula

C₁₀H₁₅NO₂

Average Molecular Weight

181.2316

Monoisotopic Molecular Weight

181.110278729

IUPAC Name

4-[1-methoxy-2-(methylamino)ethyl]phenol

Traditional Name

4-[1-methoxy-2-(methylamino)ethyl]phenol

CAS Registry Number

60094-92-0

SMILES

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

InChI Identifier

InChI=1S/C10H15NO2/c1-11-7-10(13-2)8-3-5-9(12)6-4-8/h3-6,10-12H,7H2,1-2H3

InChI Key

LVZUJPSBCGHXGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033868)
Cytoplasm (HMDB: HMDB0033868)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033868)

Source

Exogenous

Food

Food (HMDB: HMDB0033868)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0033868)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033868)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.47 g/L	ALOGPS
logP	0.76	ALOGPS
logP	0.63	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	9.1	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52 m³·mol⁻¹	ChemAxon
Polarizability	20.03 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]+	141.082	31661259
DarkChem	[M-H]-	139.249	31661259
DeepCCS	[M+H]+	140.62	30932474
DeepCCS	[M-H]-	136.868	30932474
DeepCCS	[M-2H]-	174.586	30932474
DeepCCS	[M+Na]+	150.125	30932474
AllCCS	[M+H]+	141.3	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	145.2	32859911
AllCCS	[M+Na]+	146.4	32859911
AllCCS	[M-H]-	142.5	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	144.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-O-Methylynephrine	CNCC(OC)C1=CC=C(O)C=C1	2298.7	Standard polar	33892256
beta-O-Methylynephrine	CNCC(OC)C1=CC=C(O)C=C1	1535.1	Standard non polar	33892256
beta-O-Methylynephrine	CNCC(OC)C1=CC=C(O)C=C1	1615.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-O-Methylynephrine,1TMS,isomer #1	CNCC(OC)C1=CC=C(O[Si](C)(C)C)C=C1	1527.1	Semi standard non polar	33892256
beta-O-Methylynephrine,1TMS,isomer #2	COC(CN(C)[Si](C)(C)C)C1=CC=C(O)C=C1	1761.3	Semi standard non polar	33892256
beta-O-Methylynephrine,2TMS,isomer #1	COC(CN(C)[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	1705.2	Semi standard non polar	33892256
beta-O-Methylynephrine,2TMS,isomer #1	COC(CN(C)[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1	1692.1	Standard non polar	33892256
beta-O-Methylynephrine,1TBDMS,isomer #1	CNCC(OC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1768.3	Semi standard non polar	33892256
beta-O-Methylynephrine,1TBDMS,isomer #2	COC(CN(C)[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1	1963.7	Semi standard non polar	33892256
beta-O-Methylynephrine,2TBDMS,isomer #1	COC(CN(C)[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2185.2	Semi standard non polar	33892256
beta-O-Methylynephrine,2TBDMS,isomer #1	COC(CN(C)[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2142.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-O-Methylynephrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-5900000000-049b03d7d0b9fef91b26	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-O-Methylynephrine GC-MS (1 TMS) - 70eV, Positive	splash10-00g3-9560000000-e2dd7f1975c16e7f1d7f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-O-Methylynephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 10V, Positive-QTOF	splash10-001i-0900000000-4274d6bf6b0ca0f75e78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 20V, Positive-QTOF	splash10-0ue9-0900000000-0d4823ab6e7dd76872c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 40V, Positive-QTOF	splash10-0abl-5900000000-e3faae0a31d765f6e023	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 10V, Negative-QTOF	splash10-001i-1900000000-f09b2c9ce46ad8550d09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 20V, Negative-QTOF	splash10-0f89-1900000000-dc0494606a6f31f8af94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 40V, Negative-QTOF	splash10-0006-9600000000-f6002eb516ca093325a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 10V, Positive-QTOF	splash10-0udi-0900000000-5be64244387fa45fc4cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 20V, Positive-QTOF	splash10-106r-2900000000-65989fa3c0e92f372bf9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 40V, Positive-QTOF	splash10-0a4i-4900000000-3d2d81ffa97b351fa4bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 10V, Negative-QTOF	splash10-001i-1900000000-37e5c9403eec29c678ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 20V, Negative-QTOF	splash10-0ac3-2900000000-e84a77da39be481db965	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-O-Methylynephrine 40V, Negative-QTOF	splash10-01bd-2900000000-6d7a24e03587ef661050	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012053

KNApSAcK ID

Not Available

Chemspider ID

28293888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46856263

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for beta-O-Methylynephrine (HMDB0033868)

MOL for HMDB0033868 (beta-O-Methylynephrine)

3D MOL for HMDB0033868 (beta-O-Methylynephrine)

3D SDF for HMDB0033868 (beta-O-Methylynephrine)

3D-SDF for HMDB0033868 (beta-O-Methylynephrine)

PDB for HMDB0033868 (beta-O-Methylynephrine)

3D PDB for HMDB0033868 (beta-O-Methylynephrine)

SMILES for HMDB0033868 (beta-O-Methylynephrine)

INCHI for HMDB0033868 (beta-O-Methylynephrine)

Structure for HMDB0033868 (beta-O-Methylynephrine)

3D Structure for HMDB0033868 (beta-O-Methylynephrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra