NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid (NP0187140)

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Record Information

Version

2.0

Created at

2022-09-04 03:12:33 UTC

Updated at

2022-09-04 03:12:33 UTC

NP-MRD ID

NP0187140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid

Description

Lys-Met-Met-Met, also known as K-m-m-m or KMMM, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Lys-Met-Met-Met 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-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Lys-Met-Met-Met.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205122D          

 34 33  0  0  1  0            999 V2000
    5.7750    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    6.4302    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    7.1447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6625    7.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9000    7.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9000   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875   10.7171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042205122D          

 34 33  0  0  1  0            999 V2000
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSCC[C@H](N=C(O)[C@H](CCSC)N=C(O)[C@H](CCSC)N=C(O)[C@@H](N)CCCCN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H41N5O5S3/c1-32-11-7-15(24-18(27)14(23)6-4-5-10-22)19(28)25-16(8-12-33-2)20(29)26-17(21(30)31)9-13-34-3/h14-17H,4-13,22-23H2,1-3H3,(H,24,27)(H,25,28)(H,26,29)(H,30,31)/t14-,15-,16-,17-/m0/s1

> <INCHI_KEY>
BXUPAHYBJNTSAX-QAETUUGQSA-N

> <FORMULA>
C21H41N5O5S3

> <MOLECULAR_WEIGHT>
539.77

> <EXACT_MASS>
539.226982962

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
59.923522426474

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid

> <JCHEM_LOGP>
-2.8291146576075743

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
3.6193663574005157

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1383185843175823

> <JCHEM_PKA_STRONGEST_BASIC>
10.304304424244256

> <JCHEM_POLAR_SURFACE_AREA>
187.10999999999999

> <JCHEM_REFRACTIVITY>
142.5329

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      10.780  10.669   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      11.550  12.003   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      13.090  12.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860  13.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.400  13.337   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      16.170  14.670   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      17.710  14.670   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.480  13.337   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.480  16.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.710  17.338   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.480  18.672   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      17.710  20.005   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      18.480  21.339   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      20.020  16.004   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      20.790  14.670   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.020  13.337   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.330  14.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.100  16.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.640  16.004   0.000  0.00  0.00           C+0
HETATM   20  S   UNK     0      25.410  17.338   0.000  0.00  0.00           S+0
HETATM   21  C   UNK     0      26.950  17.338   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      23.100  13.337   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      22.330  12.003   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.790  12.003   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.100  10.669   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      22.330   9.336   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      24.640  10.669   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.410   9.336   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.950   9.336   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.720   8.002   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      29.260   8.002   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      16.170  12.003   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      17.710  12.003   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      15.400  10.669   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   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32    5   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Value	Source
K-m-m-m	ChEBI
KMMM	ChEBI
L-Lys-L-met-L-met-L-met	ChEBI

Chemical Formula

C₂₁H₄₁N₅O₅S₃

Average Mass

539.7700 Da

Monoisotopic Mass

539.22698 Da

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CSCC[C@H](N=C(O)[C@H](CCSC)N=C(O)[C@H](CCSC)N=C(O)[C@@H](N)CCCCN)C(O)=O

InChI Identifier

InChI=1S/C21H41N5O5S3/c1-32-11-7-15(24-18(27)14(23)6-4-5-10-22)19(28)25-16(8-12-33-2)20(29)26-17(21(30)31)9-13-34-3/h14-17H,4-13,22-23H2,1-3H3,(H,24,27)(H,25,28)(H,26,29)(H,30,31)/t14-,15-,16-,17-/m0/s1

InChI Key

BXUPAHYBJNTSAX-QAETUUGQSA-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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetrapeptide (CHEBI:73595 )

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	-2.8	ChemAxon
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	187.11 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	142.53 m³·mol⁻¹	ChemAxon
Polarizability	59.92 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

28639378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464640

PDB ID

Not Available

ChEBI ID

73595

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid (NP0187140)

MOL for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

3D MOL for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

3D SDF for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

3D-SDF for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

PDB for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

3D PDB for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

SMILES for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

INCHI for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

Structure for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)

3D Structure for NP0187140 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2,6-diamino-1-hydroxyhexylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-4-(methylsulfanyl)butanoic acid)