NP-MRD: Showing NP-Card for trimethyllysine (NP0261223)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 03:36:31 UTC

Updated at

2022-09-08 03:36:31 UTC

NP-MRD ID

NP0261223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trimethyllysine

Description

N-Trimethyllysine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Trimethyllysine is a very strong basic compound (based on its pKa). trimethyllysine is found in Apis cerana, Himanthalia elongata, Homo sapiens, Mus musculus and Trypanosoma brucei. An alpha-amino-acid cation that is the N(6)-trimethyl derivative of L-lysine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
   -3.6750   -0.5099   -0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7241    0.0267   -0.0217 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2404   -0.2631    1.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7028    1.4652   -0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4498   -0.5850   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923    0.3907   -0.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752   -0.3942   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1942    0.5011   -0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4512   -0.2735   -0.5906 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6571   -1.3414    0.3574 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914    0.6758   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373    1.6804   -1.3029 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349    0.4445    0.2910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3368   -1.5003   -1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6796   -0.5782   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6917    0.1503   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2009   -0.8189    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4935   -0.9007    1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4310    0.6833    1.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    1.9889    0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7466    1.8367   -0.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015    1.7323   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3851   -1.1557   -1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -1.3374    0.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    1.1917   -0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    0.8147    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997   -0.8322   -1.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524   -1.2098    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207    1.2895   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2703    1.0062    0.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.7250   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -2.0490    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8178   -0.9697    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7331   -0.4341    0.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
  5 23  1  0
  5 24  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
 13 34  1  0
M  CHG  1   2   1
M  END


  Mrv0541 05041407192D          

 14 13  0  0  1  0            999 V2000
   -2.3349    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   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
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  8  1  0  0  0  0
  8 10  1  1  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
  8 14  1  1  0  0  0
M  CHG  1  11   1
M  END
> <DATABASE_ID>
NP0261223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(CCCC[N+](C)(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/p+1/t8-/m0/s1

> <INCHI_KEY>
MXNRLFUSFKVQSK-QMMMGPOBSA-O

> <FORMULA>
C9H21N2O2

> <MOLECULAR_WEIGHT>
189.2752

> <EXACT_MASS>
189.160302926

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.970316769466727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(5S)-5-amino-5-carboxypentyl]trimethylazanium

> <ALOGPS_LOGP>
-3.00

> <JCHEM_LOGP>
-6.198754912366285

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.407558396399148

> <JCHEM_PKA_STRONGEST_BASIC>
9.526420173475088

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
63.7924

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyllysine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   11                                                       
CONECT    8    6    9   10   14                                             
CONECT    9    8   12   13                                                  
CONECT   10    8                                                            
CONECT   11    1    2    3    7                                             
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(S)-2-Amino-6-(trimethylammonio)hexanoic acid	ChEBI
(S)-5-Amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium	ChEBI
epsilon-N-Trimethyl-L-lysine	ChEBI
epsilon-Trimethyl-L-lysine	ChEBI
epsilon-Trimethyllysine	ChEBI
N6,N6,N6-Trimethyl-L-lysine	ChEBI
N(epsilon)-Trimethyllysine	ChEBI
Trimethyllysine	ChEBI
(S)-2-Amino-6-(trimethylammonio)hexanoate	Generator
N-TRIMETHYLLYSINE	ChEBI
6-N-L-Trimethyl-L-lysine	MeSH
TRIMETHYLLLYSINE	MeSH
Trimethyllysine chloride, (S)-isomer	MeSH
Trimethyllysine hydroxide, inner salt, (S)-isomer	MeSH
Trimethyllysine, (+-)-isomer	MeSH
epsilon-N-Trimethyl-lysine	MeSH
Trimethyllysine hydroxide,inner salt, (+-)-isomer	MeSH
N(6),N(6),N(6)-Trimethyl-L-lysine	MeSH

Chemical Formula

C₉H₂₁N₂O₂

Average Mass

189.2752 Da

Monoisotopic Mass

189.16030 Da

IUPAC Name

[(5S)-5-amino-5-carboxypentyl]trimethylazanium

Traditional Name

trimethyllysine

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCCC[N+](C)(C)C)C(O)=O

InChI Identifier

InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/p+1/t8-/m0/s1

InChI Key

MXNRLFUSFKVQSK-QMMMGPOBSA-O

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
Apis cerana	LOTUS Database	35616633
Himanthalia elongata	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic salt
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino-acid cation (CHEBI:58100 )

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	-3	ALOGPS
logP	-6.2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	63.79 m³·mol⁻¹	ChemAxon
Polarizability	21.97 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

DB03977

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

Not Available

PDB ID

Not Available

ChEBI ID

17311

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for trimethyllysine (NP0261223)

MOL for NP0261223 (trimethyllysine)

3D MOL for NP0261223 (trimethyllysine)

3D SDF for NP0261223 (trimethyllysine)

3D-SDF for NP0261223 (trimethyllysine)

PDB for NP0261223 (trimethyllysine)

3D PDB for NP0261223 (trimethyllysine)

SMILES for NP0261223 (trimethyllysine)

INCHI for NP0261223 (trimethyllysine)

Structure for NP0261223 (trimethyllysine)

3D Structure for NP0261223 (trimethyllysine)