NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid (NP0213427)

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Record Information

Version

2.0

Created at

2022-09-05 12:24:47 UTC

Updated at

2022-09-05 12:24:47 UTC

NP-MRD ID

NP0213427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid

Description

Met-Ala, also known as L-met-L-ala or M-A, 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. Met-Ala is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid was first documented in 2019 (PMID: 31849852). Based on a literature review a small amount of articles have been published on Met-Ala (PMID: 35501295) (PMID: 34058726) (PMID: 32019204) (PMID: 30993279).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
    3.6203    1.9560    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    0.2895    0.6366 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -0.3010   -0.7234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4709   -1.6736   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6065   -1.8101    0.6996 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1631   -3.2101    0.7591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6126   -0.9853    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678   -1.0609    1.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9253   -0.2047   -0.3023 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    0.5757   -0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8835    1.8825    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7376    0.7659   -1.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2758    0.3033   -2.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9041    1.5059   -1.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4634    2.6677    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    1.9406   -0.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0829    2.3598   -0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2497    0.4506   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948   -0.3691   -1.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8841   -1.9564   -1.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -2.3740   -0.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264   -1.6173    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -3.5023   -0.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8152   -3.2538    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0599   -0.8871    2.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    0.0061    0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    2.2563    0.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7008    2.5863    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8407    1.6774    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3283    1.9820   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  1
  6 23  1  0
  6 24  1  0
  8 25  1  0
 10 26  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END


  Mrv1652309052214242D          

 14 13  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8099    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    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  1  4  0  0  0
  7  9  2  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  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC[C@H](N)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>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.65809836524236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid

> <JCHEM_LOGP>
-2.114311087357101

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.4146833621230845

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4908379906468983

> <JCHEM_PKA_STRONGEST_BASIC>
9.588721479756824

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
55.40510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       0.976   2.104   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.977  -0.206   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.645   1.334   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.978   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.978   3.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.312   1.334   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.646   2.104   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.312  -0.206   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

View in JSmol

Synonyms

Value	Source
L-Met-L-ala	ChEBI
M-A	ChEBI
MA	ChEBI
Methionylalanine	ChEBI

Chemical Formula

C₈H₁₆N₂O₃S

Average Mass

220.2900 Da

Monoisotopic Mass

220.08816 Da

IUPAC Name

(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid

Traditional Name

(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid

CAS Registry Number

Not Available

SMILES

CSCC[C@H](N)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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-2.1	ChemAxon
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	55.41 m³·mol⁻¹	ChemAxon
Polarizability	22.66 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Jannatifar R, Piroozmanesh H, Sahraei SS, Asa E: Combination of alpha lipoic acid and metformin supplement improve assisted reproductive technologies outcomes in polycystic ovary syndrome patients. Anat Cell Biol. 2022 Jun 30;55(2):239-246. doi: 10.5115/acb.21.242. Epub 2022 May 3. [PubMed:35501295 ]
Lee KH, Kuczera K: Free energy simulations to understand the effect of Met --> Ala mutations at positions 205, 206 and 213 on stability of human prion protein. Biophys Chem. 2021 Aug;275:106620. doi: 10.1016/j.bpc.2021.106620. Epub 2021 May 15. [PubMed:34058726 ]
Khavinson V, Diomede F, Mironova E, Linkova N, Trofimova S, Trubiani O, Caputi S, Sinjari B: AEDG Peptide (Epitalon) Stimulates Gene Expression and Protein Synthesis during Neurogenesis: Possible Epigenetic Mechanism. Molecules. 2020 Jan 30;25(3):609. doi: 10.3390/molecules25030609. [PubMed:32019204 ]
Li J, Zhao J, Wang X, Qayum A, Hussain MA, Liang G, Hou J, Jiang Z, Li A: Novel Angiotensin-Converting Enzyme-Inhibitory Peptides From Fermented Bovine Milk Started by Lactobacillus helveticus KLDS.31 and Lactobacillus casei KLDS.105: Purification, Identification, and Interaction Mechanisms. Front Microbiol. 2019 Nov 28;10:2643. doi: 10.3389/fmicb.2019.02643. eCollection 2019. [PubMed:31849852 ]
Miao J, Liao W, Pan Z, Wang Q, Duan S, Xiao S, Yang Z, Cao Y: Isolation and identification of iron-chelating peptides from casein hydrolysates. Food Funct. 2019 May 22;10(5):2372-2381. doi: 10.1039/c8fo02414f. [PubMed:30993279 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid (NP0213427)

MOL for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

3D MOL for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

3D SDF for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

3D-SDF for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

PDB for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

3D PDB for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

SMILES for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

INCHI for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

Structure for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)

3D Structure for NP0213427 ((2s)-2-{[(2s)-2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoic acid)