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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-08 21:41:56 UTC

Update Date

2023-02-21 17:18:41 UTC

HMDB ID

HMDB0029224

Secondary Accession Numbers

HMDB29224

Metabolite Identification

Common Name

N-methylphenylalanine

Description

2-(methylamino)-3-phenylpropanoic acid belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on 2-(methylamino)-3-phenylpropanoic acid.

Structure

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

HEADER    PROTEIN                                 08-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-12         0                                  
HETATM    1  C   UNK     0      -1.980  -0.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.314  -1.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.314  -2.915   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.980  -3.685   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.646  -2.915   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.646  -1.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.980   0.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.891   2.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.198   3.113   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.738   3.113   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.198   4.653   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       0.443   1.254   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.983   1.254   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Methylamino)-3-phenylpropanoate	Generator

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.2157

Monoisotopic Molecular Weight

179.094628665

IUPAC Name

2-(methylamino)-3-phenylpropanoic acid

Traditional Name

phenylalaninenmethyl

CAS Registry Number

Not Available

SMILES

CNC(CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C10H13NO2/c1-11-9(10(12)13)7-8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3,(H,12,13)

InChI Key

SCIFESDRCALIIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid
Secondary amine
Monocarboxylic acid or derivatives
Secondary aliphatic amine
Carboxylic acid
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.09 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.96	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.11	ChemAxon
pKa (Strongest Basic)	10.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.89 m³·mol⁻¹	ChemAxon
Polarizability	19 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.795	31661259
DarkChem	[M-H]-	140.323	31661259
DeepCCS	[M+H]+	134.855	30932474
DeepCCS	[M-H]-	131.026	30932474
DeepCCS	[M-2H]-	168.21	30932474
DeepCCS	[M+Na]+	143.75	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.1	32859911
AllCCS	[M+NH4]+	144.3	32859911
AllCCS	[M+Na]+	145.5	32859911
AllCCS	[M-H]-	140.0	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.03 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9207 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	195.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-methylphenylalanine	CNC(CC1=CC=CC=C1)C(O)=O	2362.4	Standard polar	33892256
N-methylphenylalanine	CNC(CC1=CC=CC=C1)C(O)=O	1543.9	Standard non polar	33892256
N-methylphenylalanine	CNC(CC1=CC=CC=C1)C(O)=O	1591.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-methylphenylalanine,1TMS,isomer #1	CNC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C	1526.9	Semi standard non polar	33892256
N-methylphenylalanine,1TMS,isomer #2	CN(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	1672.8	Semi standard non polar	33892256
N-methylphenylalanine,2TMS,isomer #1	CN(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1675.8	Semi standard non polar	33892256
N-methylphenylalanine,2TMS,isomer #1	CN(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1673.5	Standard non polar	33892256
N-methylphenylalanine,1TBDMS,isomer #1	CNC(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	1771.3	Semi standard non polar	33892256
N-methylphenylalanine,1TBDMS,isomer #2	CN(C(CC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	1897.2	Semi standard non polar	33892256
N-methylphenylalanine,2TBDMS,isomer #1	CN(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2139.4	Semi standard non polar	33892256
N-methylphenylalanine,2TBDMS,isomer #1	CN(C(CC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2124.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9500000000-de7b5a69fa52fc116a8d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9530000000-c830d0ef4d57e419ebf0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-methylphenylalanine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - N-methylphenylalanine 10V, Positive-QTOF	splash10-001i-0900000000-6e7dd98dbe82a34d8509	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 20V, Positive-QTOF	splash10-001i-0900000000-f7af8ab7da7641f4418b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 40V, Positive-QTOF	splash10-0pbc-7900000000-7d90cb1edd8e6b6846b8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 10V, Negative-QTOF	splash10-004i-0900000000-0f8868123728a808ba8d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 20V, Negative-QTOF	splash10-0059-1900000000-fdf03cb6bb7134893864	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 40V, Negative-QTOF	splash10-0f7o-5900000000-9be75aa426fca11c6122	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 10V, Positive-QTOF	splash10-001i-0900000000-bd25b317e147a762d9f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 20V, Positive-QTOF	splash10-0563-7900000000-833e19bef2e229747402	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 40V, Positive-QTOF	splash10-0f96-9300000000-cb79beeb3a36154e2663	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 10V, Negative-QTOF	splash10-004i-0900000000-a72b56f6c5226aa9250c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 20V, Negative-QTOF	splash10-0ufu-5900000000-dd823d819f6e309b2d2a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-methylphenylalanine 40V, Negative-QTOF	splash10-0f96-9400000000-5406f3e8c81a68653e9e	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)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3846742

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for N-methylphenylalanine (HMDB0029224)

MOL for HMDB0029224 (N-methylphenylalanine)

3D MOL for HMDB0029224 (N-methylphenylalanine)

3D SDF for HMDB0029224 (N-methylphenylalanine)

3D-SDF for HMDB0029224 (N-methylphenylalanine)

PDB for HMDB0029224 (N-methylphenylalanine)

3D PDB for HMDB0029224 (N-methylphenylalanine)

SMILES for HMDB0029224 (N-methylphenylalanine)

INCHI for HMDB0029224 (N-methylphenylalanine)

Structure for HMDB0029224 (N-methylphenylalanine)

3D Structure for HMDB0029224 (N-methylphenylalanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra