NP-MRD: Showing NP-Card for Methionyl-Methionine (NP0136580)

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Record Information

Version

2.0

Created at

2022-05-12 15:18:13 UTC

Updated at

2022-05-12 15:18:13 UTC

NP-MRD ID

NP0136580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methionyl-Methionine

Description

Methionyl-Methionine, also known as m-m dipeptide or met-met, 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-Methionine is a very strong basic compound (based on its pKa). Methionyl-Methionine is a dipeptied compoosed of two methionine residues. 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. It is an incomplete breakdown product of protein digestion or protein catabolism. Methionyl-Methionine was first documented in 1984 (PMID: 6693991). This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite (PMID: 10911722) (PMID: 3351635).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -4.9624   -1.4414   -2.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6998   -1.7360   -0.3705 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892   -0.2161    0.5541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0857    0.4323    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022   -0.4755    0.4052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8291   -0.8115    1.8101 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    0.2131   -0.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5547    0.5810   -1.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3997    0.5003    0.8514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978    1.1763    0.4252 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8388    0.3675    0.6266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8072   -0.9352   -0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -1.8929    0.1278 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7614   -1.0521   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7149    2.5152    1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8168    2.8895    1.8997 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7739    3.3599    0.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1831   -2.0434   -2.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9109   -0.3879   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9355   -1.8595   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4470   -0.4220    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1944    0.5097    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0911    0.7192   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9715    1.3416    0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0213   -1.4156   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -1.4145    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6978    0.0481    2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775    0.1840    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4958    1.3917   -0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6815    0.9623    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1198    0.2274    1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -0.7098   -1.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9453   -1.5766    0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5541    0.0308   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8926   -1.3833   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985   -1.2889   -0.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    3.6124   -0.0522 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  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  6
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
M  END


  Mrv1652304062014032D          

 17 16  0  0  0  0            999 V2000
    3.5211    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    4.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    1.6204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    1.6204    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  0  0  0  0
  6  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136580

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H20N2O3S2/c1-16-5-3-7(11)9(13)12-8(10(14)15)4-6-17-2/h7-8H,3-6,11H2,1-2H3,(H,12,13)(H,14,15)

> <INCHI_KEY>
ZYTPOUNUXRBYGW-UHFFFAOYSA-N

> <FORMULA>
C10H20N2O3S2

> <MOLECULAR_WEIGHT>
280.407

> <EXACT_MASS>
280.091533896

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.936296445773856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-2.0769274215217406

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.777711132765926

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8602350374867984

> <JCHEM_PKA_STRONGEST_BASIC>
8.415887266937473

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
71.9721

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       7.906   6.105   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      13.241   6.105   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.575   3.795   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      15.908   7.645   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0      19.909   5.335   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0      21.243   6.105   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.907   3.795   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.241   3.025   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.574   3.025   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   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
L-Methionyl-L-methionine	HMDB
m-m Dipeptide	HMDB
Met-met	HMDB
Methionine methionine dipeptide	HMDB
Methionine-methionine dipeptide	HMDB
Methionylmethionine	HMDB
MM Dipeptide	HMDB
Methionylmethionine, (L-met-L-met)-isomer	HMDB
DL-Methionylmethionine	HMDB
2-{[2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoate	Generator
2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-4-(methylsulphanyl)butanoate	Generator
2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-4-(methylsulphanyl)butanoic acid	Generator

Chemical Formula

C₁₀H₂₀N₂O₃S₂

Average Mass

280.4070 Da

Monoisotopic Mass

280.09153 Da

IUPAC Name

2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid

Traditional Name

2-[2-amino-4-(methylsulfanyl)butanamido]-4-(methylsulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H20N2O3S2/c1-16-5-3-7(11)9(13)12-8(10(14)15)4-6-17-2/h7-8H,3-6,11H2,1-2H3,(H,12,13)(H,14,15)

InChI Key

ZYTPOUNUXRBYGW-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
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Thia fatty acid
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Amino acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Sulfenyl compound
Thioether
Dialkylthioether
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
Primary amine
Organic oxygen compound
Amine
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	-0.42	ALOGPS
logP	-2.1	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.86	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	71.97 m³·mol⁻¹	ChemAxon
Polarizability	29.94 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

HMDB0028979

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

104294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hug GL, Bobrowski K, Kozubek H, Marciniak B: Photo-oxidation of methionine-containing peptides by the 4-carboxybenzophenone triplet state in aqueous solution. Competition between intramolecular two-centered three-electron bonded (S...S)+ and (S...N)+ formation. Photochem Photobiol. 2000 Jul;72(1):1-9. doi: 10.1562/0031-8655(2000)072<0001:poomcp>2.0.co;2. [PubMed:10911722 ]
Baker DH, Bafundo KW, Boebel KP, Czarnecki GL, Halpin KM: Methionine peptides as potential food supplements: efficacy and susceptibility to Maillard browning. J Nutr. 1984 Feb;114(2):292-7. doi: 10.1093/jn/114.2.292. [PubMed:6693991 ]
Friedman M, Gumbmann MR: Nutritional value and safety of methionine derivatives, isomeric dipeptides and hydroxy analogs in mice. J Nutr. 1988 Mar;118(3):388-97. doi: 10.1093/jn/118.3.388. [PubMed:3351635 ]

Showing NP-Card for Methionyl-Methionine (NP0136580)

MOL for NP0136580 (Methionyl-Methionine)

3D MOL for NP0136580 (Methionyl-Methionine)

3D SDF for NP0136580 (Methionyl-Methionine)

3D-SDF for NP0136580 (Methionyl-Methionine)

PDB for NP0136580 (Methionyl-Methionine)

3D PDB for NP0136580 (Methionyl-Methionine)

SMILES for NP0136580 (Methionyl-Methionine)

INCHI for NP0136580 (Methionyl-Methionine)

Structure for NP0136580 (Methionyl-Methionine)

3D Structure for NP0136580 (Methionyl-Methionine)