MiMeDB: Showing metabocard for L-methionyl-L-alanine (MMDBc0049919)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:46:17 UTC

Update Date

2025-10-07 16:08:14 UTC

Metabolite ID

MMDBc0049919

Metabolite Identification

Common Name

L-methionyl-L-alanine

Description

L-methionyl-L-alanine is a dipeptide belonging to the class of amino acid derivatives. Its chemical structure is represented by the formula C(8)H(16)N(2)O(3)S, featuring a combination of methionine and alanine residues. The crystal structure of this dipeptide exhibits hexagonal symmetry with a Z' value of 7, indicating a complex arrangement in solid-state forms (PMID:14532680 ). L-methionyl-L-alanine's structural characteristics are closely related to those of other dipeptides, such as L-valyl-L-alanine, suggesting potential similarities in biochemical interactions (PMID:14532680 ). In biological contexts, L-methionyl-L-alanine may participate in various metabolic pathways, including those involving acylase I and N-acylpeptide hydrolase activities, as evidenced by studies on its N-acetyl derivatives in primary rat hepatocyte cultures (PMID:12000146 ). Furthermore, it is noted in research focusing on the synthesis and properties of sequenced copolypeptides, highlighting its relevance in peptide chemistry (PMID:5503404 ). Overall, L-methionyl-L-alanine serves as an important compound in both chemical and biological research.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304302200462D          

 14 13  0  0  1  0            999 V2000
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2849    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  CHG  2   6   1  13  -1
M  END
> <DATABASE_ID>
MMDBc0049919

> <DATABASE_NAME>
MIME

> <SMILES>
CSCC[C@H]([NH3+])C(=O)N[C@@H](C)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16N2O3S/c1-5(8(12)13)10-7(11)6(9)3-4-14-2/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

> <INCHI_KEY>
JHKXZYLNVJRAAJ-WDSKDSINSA-N

> <FORMULA>
C8H16N2O3S

> <MOLECULAR_WEIGHT>
220.29

> <EXACT_MASS>
220.088163557

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.76975041383621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-azaniumyl-4-(methylsulfanyl)butanamido]propanoate

> <ALOGPS_LOGP>
-1.32

> <JCHEM_LOGP>
-2.7283118252400533

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.887620779813048

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8087427399580087

> <JCHEM_PKA_STRONGEST_BASIC>
8.415886085992366

> <JCHEM_POLAR_SURFACE_AREA>
96.87

> <JCHEM_REFRACTIVITY>
77.01330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-ammonio-4-(methylsulfanyl)butanamido]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-APR-22         0                                  
HETATM    1  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       5.596   4.771   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.597   2.461   0.000  0.00  0.00           N+1
HETATM    7  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      12.265   4.001   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.598   6.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O-1
HETATM   14  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
M-A	ChEBI
MA	ChEBI
Methionylalanine	ChEBI

Molecular Formula

C₈H₁₆N₂O₃S

Average Mass

220.29

Monoisotopic Mass

220.088163557

IUPAC Name

(2S)-2-[(2S)-2-azaniumyl-4-(methylsulfanyl)butanamido]propanoate

Traditional Name

(2S)-2-[(2S)-2-ammonio-4-(methylsulfanyl)butanamido]propanoate

CAS Registry Number

Not Available

SMILES

CSCC[C@H]([NH3+])C(=O)N[C@@H](C)C([O-])=O

InChI Identifier

InChI=1S/C8H16N2O3S/c1-5(8(12)13)10-7(11)6(9)3-4-14-2/h5-6H,3-4,9H2,1-2H3,(H,10,11)(H,12,13)/t5-,6-/m0/s1

InChI Key

JHKXZYLNVJRAAJ-WDSKDSINSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Methionine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxamide group
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organosulfur compound
Amine
Organic oxygen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73610 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.16 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.87 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.01 m³·mol⁻¹	ChemAxon
Polarizability	22.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

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	201.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	73.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	318.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	466.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	293.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	295.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	1417.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	147.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	677.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	237.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	373.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	170.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	87.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	133.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	436.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	74.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	259.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1004.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	809.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	L-methionyl-L-alanine_TMS_1	CSCC[C@H]([NH3+])C(=O)N([C@@H](C)C(=O)[O-])[Si](C)(C)C	standard non polar	2025-10-24	2021.48
Gas Chromatography	L-methionyl-L-alanine_TMS_1	CSCC[C@H]([NH3+])C(=O)N([C@@H](C)C(=O)[O-])[Si](C)(C)C	standard polar	2025-10-24	1979.7

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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/Eubacteria	Firmicutes	387	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Cattle ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	178	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	129	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	129	Human feces; Human appendix biopsy; Human ; Human urine; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Firmicutes	2	Human feces; Human pleural fluid plaque; Pig ; Human ; Human supragingival plaque; Human saliva; Cattle ; Human subgingival plaque	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB

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

5373160

KEGG Compound ID

Not Available

BioCyc ID

CPD-13390

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7009580

PDB ID

Not Available

ChEBI ID

73610

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for L-methionyl-L-alanine (MMDBc0049919)

MOL for #<Metabolite:0x00007f9ac6302678>

3D MOL for #<Metabolite:0x00007f9ac6302678>

3D SDF for #<Metabolite:0x00007f9ac6302678>

3D-SDF for #<Metabolite:0x00007f9ac6302678>

PDB for #<Metabolite:0x00007f9ac6302678>

3D PDB for #<Metabolite:0x00007f9ac6302678>

SMILES for #<Metabolite:0x00007f9ac6302678>

INCHI for #<Metabolite:0x00007f9ac6302678>

Structure for #<Metabolite:0x00007f9ac6302678>

3D Structure for #<Metabolite:0x00007f9ac6302678>