NP-MRD: Showing NP-Card for Methionyl-Alanine (NP0122871)

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Record Information

Version

2.0

Created at

2022-05-12 09:13:27 UTC

Updated at

2022-05-12 09:13:27 UTC

NP-MRD ID

NP0122871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methionyl-Alanine

Description

Methionyl-Alanine, also known as m-a dipeptide or met-ala, 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. Methionyl-Alanine is a very strong basic compound (based on its pKa). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. It is an incomplete breakdown product of protein digestion or protein catabolism. Methionyl-Alanine is a dipeptide composed of methionine and alanine. Methionyl-Alanine was first documented in 1990 (PMID: 2178223). Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
    4.2897    0.7524    0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    0.7985   -0.9440 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7839   -0.3597   -1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4983    0.1885   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3529   -0.7614   -1.1721 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3080   -0.8378   -2.6165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -0.2798   -0.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3860    0.9583   -0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5417   -0.9952    0.2527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612   -0.5112    0.8225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6319    0.9431    1.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030   -1.2772    2.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211   -2.2378    2.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.9262    2.6489 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2513    1.2323    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218    1.2900    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368   -0.3180    1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7115   -0.5023   -2.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -1.3150   -0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    0.3330    0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3168    1.1625   -1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -1.7579   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8150   -0.0912   -3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -1.7809   -2.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5723    1.2126   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5705   -0.5937    0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1366    1.1136    2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1390    1.5696    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    1.1944    1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831   -0.8601    3.6444 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  6
 11 27  1  0
 11 28  1  0
 11 29  1  0
 14 30  1  0
M  END


  Mrv1652304032018462D          

 14 13  0  0  0  0            999 V2000
    4.3974    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  4  0  0  0
 10  7  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0122871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCCC(N)C(O)=NC(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)

> <INCHI_KEY>
JHKXZYLNVJRAAJ-UHFFFAOYSA-N

> <FORMULA>
C8H16N2O3S

> <MOLECULAR_WEIGHT>
220.289

> <EXACT_MASS>
220.088163078

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.19256747519072

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-2.114311087357101

> <ALOGPS_LOGS>
-1.88

> <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>
55.405100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0       8.208   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.207  -1.540   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       6.875   0.000   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       5.541   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.876   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       9.542  -1.540   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       0.206   0.770   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2   14                                                            
CONECT    3    4    6                                                       
CONECT    4    3   14                                                       
CONECT    5    1    8   10                                                  
CONECT    6    3    7    9                                                  
CONECT    7    6   10   11                                                  
CONECT    8    5   12   13                                                  
CONECT    9    6                                                            
CONECT   10    5    7                                                       
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    2    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
L-Methionyl-L-alanine	HMDB
m-a Dipeptide	HMDB
MA dipeptide	HMDB
Met-ala	HMDB
Methionine alanine dipeptide	HMDB
Methionine-alanine dipeptide	HMDB
Methionylalanine	HMDB
2-{[2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}propanoate	Generator
2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}propanoate	Generator
2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}propanoic acid	Generator

Chemical Formula

C₈H₁₆N₂O₃S

Average Mass

220.2890 Da

Monoisotopic Mass

220.08816 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CSCCC(N)C(O)=NC(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)

InChI Key

JHKXZYLNVJRAAJ-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	-1.7	ALOGPS
logP	-2.1	ChemAxon
logS	-1.9	ALOGPS
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	23.19 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

HMDB0028966

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14878381

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Binder L, Gertler A, Elberg G, Guy R, Vogel T: Site-directed mutations of human growth hormone that selectively modify its lactogenic activity and binding properties. Mol Endocrinol. 1990 Jul;4(7):1060-8. doi: 10.1210/mend-4-7-1060. [PubMed:2178223 ]

Showing NP-Card for Methionyl-Alanine (NP0122871)

MOL for NP0122871 (Methionyl-Alanine)

3D MOL for NP0122871 (Methionyl-Alanine)

3D SDF for NP0122871 (Methionyl-Alanine)

3D-SDF for NP0122871 (Methionyl-Alanine)

PDB for NP0122871 (Methionyl-Alanine)

3D PDB for NP0122871 (Methionyl-Alanine)

SMILES for NP0122871 (Methionyl-Alanine)

INCHI for NP0122871 (Methionyl-Alanine)

Structure for NP0122871 (Methionyl-Alanine)

3D Structure for NP0122871 (Methionyl-Alanine)