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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:45:33 UTC

Update Date

2021-09-26 22:54:19 UTC

HMDB ID

HMDB0245704

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl l-phenylalaninate

Description

Methyl l-phenylalaninate 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 a significant number of articles have been published on Methyl l-phenylalaninate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methyl l-phenylalaninate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methyl l-phenylalaninate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
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
Methyl L-phenylalaninic acid	Generator
Methyl 2-amino-3-phenylpropanoic acid	HMDB

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.219

Monoisotopic Molecular Weight

179.094628663

IUPAC Name

methyl 2-amino-3-phenylpropanoate

Traditional Name

methyl 2-amino-3-phenylpropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(N)CC1=CC=CC=C1

InChI Identifier

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

InChI Key

VSDUZFOSJDMAFZ-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
Alpha-amino acid ester
Amphetamine or derivatives
Fatty acid ester
Aralkylamine
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	0.8	ALOGPS
logP	1.22	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	6.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.89 m³·mol⁻¹	ChemAxon
Polarizability	19.37 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
DeepCCS	[M+H]+	139.802	30932474
DeepCCS	[M-H]-	136.604	30932474
DeepCCS	[M-2H]-	173.437	30932474
DeepCCS	[M+Na]+	148.975	30932474
AllCCS	[M+H]+	142.0	32859911
AllCCS	[M+H-H2O]+	138.0	32859911
AllCCS	[M+NH4]+	145.7	32859911
AllCCS	[M+Na]+	146.8	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	141.8	32859911
AllCCS	[M+HCOO]-	143.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl l-phenylalaninate	COC(=O)C(N)CC1=CC=CC=C1	2195.2	Standard polar	33892256
Methyl l-phenylalaninate	COC(=O)C(N)CC1=CC=CC=C1	1392.0	Standard non polar	33892256
Methyl l-phenylalaninate	COC(=O)C(N)CC1=CC=CC=C1	1473.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl l-phenylalaninate,1TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	1507.9	Semi standard non polar	33892256
Methyl l-phenylalaninate,1TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	1580.1	Standard non polar	33892256
Methyl l-phenylalaninate,1TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	2100.3	Standard polar	33892256
Methyl l-phenylalaninate,2TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1710.1	Semi standard non polar	33892256
Methyl l-phenylalaninate,2TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1693.9	Standard non polar	33892256
Methyl l-phenylalaninate,2TMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2048.1	Standard polar	33892256
Methyl l-phenylalaninate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1721.4	Semi standard non polar	33892256
Methyl l-phenylalaninate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	1774.3	Standard non polar	33892256
Methyl l-phenylalaninate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	2215.8	Standard polar	33892256
Methyl l-phenylalaninate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2126.1	Semi standard non polar	33892256
Methyl l-phenylalaninate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2108.6	Standard non polar	33892256
Methyl l-phenylalaninate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2246.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl l-phenylalaninate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-89fac023295d166e079b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl l-phenylalaninate 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 - Methyl l-phenylalaninate 10V, Positive-QTOF	splash10-00di-0900000000-b79ae03ae9ec95a26ec7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl l-phenylalaninate 20V, Positive-QTOF	splash10-00di-3900000000-8cf1a819ead97795d639	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl l-phenylalaninate 40V, Positive-QTOF	splash10-0ufr-9800000000-5a5d104817aa611209a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl l-phenylalaninate 10V, Negative-QTOF	splash10-004i-2900000000-40fd3bd6a0652ee12e8d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl l-phenylalaninate 20V, Negative-QTOF	splash10-0f97-4900000000-3ee8b9398c465b28f3c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl l-phenylalaninate 40V, Negative-QTOF	splash10-004i-8900000000-dae987ea817d285c39fa	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75737

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Methyl l-phenylalaninate (HMDB0245704)

MOL for HMDB0245704 (Methyl l-phenylalaninate)

3D MOL for HMDB0245704 (Methyl l-phenylalaninate)

3D SDF for HMDB0245704 (Methyl l-phenylalaninate)

3D-SDF for HMDB0245704 (Methyl l-phenylalaninate)

PDB for HMDB0245704 (Methyl l-phenylalaninate)

3D PDB for HMDB0245704 (Methyl l-phenylalaninate)

SMILES for HMDB0245704 (Methyl l-phenylalaninate)

INCHI for HMDB0245704 (Methyl l-phenylalaninate)

Structure for HMDB0245704 (Methyl l-phenylalaninate)

3D Structure for HMDB0245704 (Methyl l-phenylalaninate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra