MiMeDB: Showing metabocard for (2S,3S)-3-methylphenylalanine (MMDBc0054053)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:48:33 UTC

Update Date

2025-10-07 16:08:21 UTC

Metabolite ID

MMDBc0054053

Metabolite Identification

Common Name

(2S,3S)-3-methylphenylalanine

Description

(2S,3S)-3-methylphenylalanine is a non-proteinogenic amino acid classified as a metabolite. Its chemical structure features a phenylalanine backbone with a methyl group at the third carbon, contributing to its unique properties. This compound is involved in various metabolic pathways, particularly those related to amino acid biosynthesis and degradation. It has been identified in predictive models assessing metabolic profiles, indicating its potential relevance in disease states. Notably, studies have shown that the levels of (2S,3S)-3-methylphenylalanine, along with other metabolites, are significantly altered in different stages of cancer, with higher concentrations observed in early cancer compared to advanced stages (PMID:35155234 ). This suggests a role in metabolic changes associated with tumor progression. The understanding of (2S,3S)-3-methylphenylalanine's involvement in these pathways may provide insights into its potential as a biomarker or therapeutic target in oncological research.

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      19.461 -18.007   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.461 -19.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.070 -20.403   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.757 -19.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.757 -18.007   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.070 -17.234   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.774 -17.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.088 -18.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.402 -17.234   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.715 -18.007   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      23.402 -15.689   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      22.088 -19.630   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      20.774 -15.694   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    5    1                                                       
CONECT    7    1    8   13                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
(2S,3S)-2-Ammonio-3-phenylbutanoate	ChEBI
(2S,3S)-3-Methylphenylalanine	ChEBI
(3S)-3-Methyl-L-phenylalanine zwitterion	ChEBI
(BetaS)-beta-methyl-L-phenylalanine zwitterion	ChEBI
(2S,3S)-2-Ammonio-3-phenylbutanoic acid	Generator
(BetaS)-b-methyl-L-phenylalanine zwitterion	Generator
(BetaS)-β-methyl-L-phenylalanine zwitterion	Generator
(2S,3S)-b-Methylphenylalanine zwitterion	Generator
(2S,3S)-Β-methylphenylalanine zwitterion	Generator

Molecular Formula

C₁₀H₁₃NO₂

Average Mass

179.219

Monoisotopic Mass

179.094628663

IUPAC Name

(2S,3S)-2-amino-3-phenylbutanoic acid

Traditional Name

(2S,3S)-2-amino-3-phenylbutanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H]([C@H](N)C(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H13NO2/c1-7(9(11)10(12)13)8-5-3-2-4-6-8/h2-7,9H,11H2,1H3,(H,12,13)/t7-,9-/m0/s1

InChI Key

IRZQDMYEJPNDEN-CBAPKCEASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:77031 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.07 g/L	ALOGPS
logP	-0.96	ALOGPS
logP	-0.82	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.54	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.59 m³·mol⁻¹	ChemAxon
Polarizability	18.98 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-70f6dfde19556e4b2d07	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-ed09a9b24340eb944d87	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-7900000000-4d32339a18ec16b861e4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-79dfcac97aab90747864	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05i0-7900000000-dd3bd67496e33c9eeb9e	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i0-9200000000-5a298353639662fe8c82	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	352.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	213.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	277.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	305.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	291.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	303.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	845.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	460.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	391.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	181.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	365.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	178.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	105.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	111.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	387.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	73.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	254.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	796.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	731.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_1	C[C@@H](C1=CC=CC=C1)[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1690.64
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_2	C[C@@H](C1=CC=CC=C1)[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1861.84
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_3	C[C@@H](C1=CC=CC=C1)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1776.58
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_4	C[C@@H](C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2237.66
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_5	C[C@@H](C1=CC=CC=C1)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2635.41
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_1	C[C@@H](C1=CC=CC=C1)[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1900.67
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_2	C[C@@H](C1=CC=CC=C1)[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2540.61
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_3	C[C@@H](C1=CC=CC=C1)[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1571.81
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_4	C[C@@H](C1=CC=CC=C1)[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2292.85
Gas Chromatography	(2S,3S)-3-methylphenylalanine_TMS_5	C[C@@H](C1=CC=CC=C1)[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2246.12

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-15345

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

854352

PDB ID

Not Available

ChEBI ID

76864

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (2S,3S)-3-methylphenylalanine (MMDBc0054053)

MOL for #<Metabolite:0x00007f9ad8b863f0>

3D MOL for #<Metabolite:0x00007f9ad8b863f0>

3D SDF for #<Metabolite:0x00007f9ad8b863f0>

3D-SDF for #<Metabolite:0x00007f9ad8b863f0>

PDB for #<Metabolite:0x00007f9ad8b863f0>

3D PDB for #<Metabolite:0x00007f9ad8b863f0>

SMILES for #<Metabolite:0x00007f9ad8b863f0>

INCHI for #<Metabolite:0x00007f9ad8b863f0>

Structure for #<Metabolite:0x00007f9ad8b863f0>

3D Structure for #<Metabolite:0x00007f9ad8b863f0>