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Showing NP-Card for Lysyl-Lysine (NP0339523)

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Record Information
Version2.0
Created at2024-09-11 22:15:40 UTC
Updated at2024-09-11 22:15:40 UTC
NP-MRD IDNP0339523
Secondary Accession NumbersNone
Natural Product Identification
Common NameLysyl-Lysine
Description Lysyl-Lysine was first documented in 2006 (PMID: 16720029). Based on a literature review a significant number of articles have been published on Lysyl-Lysine (PMID: 24891507) (PMID: 35481706) (PMID: 22128152) (PMID: 21291379) (PMID: 20417276) (PMID: 18621422).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339523 (Lysyl-Lysine)


  Mrv2104 05272300472D          

 19 18  0  0  0  0            999 V2000
    3.7125   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   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
    3.3000   -8.5737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  4  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
M  END
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3D MOL for NP0339523 (Lysyl-Lysine)

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3D SDF for NP0339523 (Lysyl-Lysine)

  Mrv2104 05272300472D          

 19 18  0  0  0  0            999 V2000
    3.7125   -6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -4.2868    0.0000 C   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
    3.3000   -8.5737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -5.0013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  4  0  0  0
 16 11  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCCC(N)C(O)=NC(CCCCN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C12H26N4O3/c13-7-3-1-5-9(15)11(17)16-10(12(18)19)6-2-4-8-14/h9-10H,1-8,13-15H2,(H,16,17)(H,18,19)

> <INCHI_KEY>
NVGBPTNZLWRQSY-UHFFFAOYNA-N

> <FORMULA>
C12H26N4O3

> <MOLECULAR_WEIGHT>
274.365

> <EXACT_MASS>
274.200490713

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.024621676205584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-2-[(2,6-diamino-1-hydroxyhexylidene)amino]hexanoic acid

> <JCHEM_LOGP>
-5.452351701590692

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
4.31470628171633

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5756995374611575

> <JCHEM_PKA_STRONGEST_BASIC>
10.558734953047713

> <JCHEM_POLAR_SURFACE_AREA>
147.95

> <JCHEM_REFRACTIVITY>
72.9408

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-2-[(2,6-diamino-1-hydroxyhexylidene)amino]hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339523 (Lysyl-Lysine)
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PDB for NP0339523 (Lysyl-Lysine)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       6.930 -12.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.160 -13.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160 -10.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930 -14.671   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.930  -9.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.160  -5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.160  -8.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.160 -16.004   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000  -2.667   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       8.470  -9.336   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       6.930  -6.668   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.620  -8.002   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.470  -4.001   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   13                                                       
CONECT    8    4   14                                                       
CONECT    9    5   11   15                                                  
CONECT   10    6   12   16                                                  
CONECT   11    9   16   17                                                  
CONECT   12   10   18   19                                                  
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    9                                                            
CONECT   16   10   11                                                       
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

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3D PDB for NP0339523 (Lysyl-Lysine)
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SMILES for NP0339523 (Lysyl-Lysine)
NCCCCC(N)C(O)=NC(CCCCN)C(O)=O
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INCHI for NP0339523 (Lysyl-Lysine)
InChI=1/C12H26N4O3/c13-7-3-1-5-9(15)11(17)16-10(12(18)19)6-2-4-8-14/h9-10H,1-8,13-15H2,(H,16,17)(H,18,19)
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H26N4O3
Average Mass274.3650 Da
Monoisotopic Mass274.20049 Da
IUPAC Name6-amino-2-[(2,6-diamino-1-hydroxyhexylidene)amino]hexanoic acid
Traditional Name6-amino-2-[(2,6-diamino-1-hydroxyhexylidene)amino]hexanoic acid
CAS Registry NumberNot Available
SMILES
NCCCCC(N)C(O)=NC(CCCCN)C(O)=O
InChI Identifier
InChI=1/C12H26N4O3/c13-7-3-1-5-9(15)11(17)16-10(12(18)19)6-2-4-8-14/h9-10H,1-8,13-15H2,(H,16,17)(H,18,19)
InChI KeyNVGBPTNZLWRQSY-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-5.5ChemAxon
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)10.56ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area147.95 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity72.94 m³·mol⁻¹ChemAxon
Polarizability31.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Veiga-da-Cunha M, Chevalier N, Stroobant V, Vertommen D, Van Schaftingen E: Metabolite proofreading in carnosine and homocarnosine synthesis: molecular identification of PM20D2 as beta-alanyl-lysine dipeptidase. J Biol Chem. 2014 Jul 11;289(28):19726-36. doi: 10.1074/jbc.M114.576579. Epub  2014 Jun 2. [PubMed:24891507  ] 
  2. Kirupananthan D, Bertolo RF, Brunton JA: Lysine Dipeptide Enhances Gut Structure and Whole-Body Protein Synthesis in Neonatal Piglets with Intestinal Atrophy. J Nutr. 2022 Aug 9;152(8):1843-1850. doi: 10.1093/jn/nxac095. [PubMed:35481706  ] 
  3. Park JH, Johansson HE, Aoki H, Huang BX, Kim HY, Ganoza MC, Park MH: Post-translational modification by beta-lysylation is required for activity of Escherichia coli elongation factor P (EF-P). J Biol Chem. 2012 Jan 20;287(4):2579-90. doi: 10.1074/jbc.M111.309633. Epub 2011  Nov 29. [PubMed:22128152  ] 
  4. Singh J, Yang P, Michel D, Verrall RE, Foldvari M, Badea I: Amino acid-substituted gemini surfactant-based nanoparticles as safe and versatile gene delivery agents. Curr Drug Deliv. 2011 May;8(3):299-306. doi: 10.2174/156720111795256200. [PubMed:21291379  ] 
  5. Yang P, Singh J, Wettig S, Foldvari M, Verrall RE, Badea I: Enhanced gene expression in epithelial cells transfected with amino acid-substituted gemini nanoparticles. Eur J Pharm Biopharm. 2010 Aug;75(3):311-20. doi: 10.1016/j.ejpb.2010.04.007.  Epub 2010 Apr 22. [PubMed:20417276  ] 
  6. Farhat K, Sauter KS, Brcic M, Frey J, Ulmer AJ, Jungi TW: The response of HEK293 cells transfected with bovine TLR2 to established pathogen-associated molecular patterns and to bacteria causing mastitis in cattle. Vet Immunol Immunopathol. 2008 Oct 15;125(3-4):326-36. doi:  10.1016/j.vetimm.2008.05.026. Epub 2008 Jun 6. [PubMed:18621422  ] 
  7. Prasad S, Mathur A, Jaggi M, Mukherjee R: Delivering multiple anticancer peptides as a single prodrug using lysyl-lysine as a facile linker. J Pept Sci. 2007 Jul;13(7):458-67. doi: 10.1002/psc.867. [PubMed:17559067  ] 
  8. Remer KA, Brcic M, Sauter KS, Jungi TW: Human monocytoid cells as a model to study Toll-like receptor-mediated activation. J Immunol Methods. 2006 Jun 30;313(1-2):1-10. doi: 10.1016/j.jim.2005.07.026.  Epub 2006 Apr 25. [PubMed:16720029  ] 
  9. Ryge TS, Hansen PR: Potent antibacterial lysine-peptoid hybrids identified from a positional scanning combinatorial library. Bioorg Med Chem. 2006 Jul 1;14(13):4444-51. doi: 10.1016/j.bmc.2006.02.034. Epub  2006 Mar 9. [PubMed:16524733  ]