MiMeDB: Showing metabocard for N(6),N(6),N(6)-trimethyl-L-lysine (MMDBc0054601)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:20:34 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054601

Metabolite Identification

Common Name

N(6),N(6),N(6)-trimethyl-L-lysine

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). An alpha-amino-acid cation that is the N(6)-trimethyl derivative of L-lysine.

Structure

MOL SDF PDB SMILES InChI


  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>
MMDBc0054601

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₉H₂₁N₂O₂

Average Mass

189.2752

Monoisotopic Mass

189.160302926

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldi-2900000000-08b81c9b9c1922668ebc	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9300000000-590d246e1fc6132b9928	2017-08-28	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB03977

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N(6),N(6),N(6)-trimethyl-L-lysine (MMDBc0054601)

MOL for #<Metabolite:0x00007fed1595f7b8>

3D MOL for #<Metabolite:0x00007fed1595f7b8>

3D SDF for #<Metabolite:0x00007fed1595f7b8>

3D-SDF for #<Metabolite:0x00007fed1595f7b8>

PDB for #<Metabolite:0x00007fed1595f7b8>

3D PDB for #<Metabolite:0x00007fed1595f7b8>

SMILES for #<Metabolite:0x00007fed1595f7b8>

INCHI for #<Metabolite:0x00007fed1595f7b8>

Structure for #<Metabolite:0x00007fed1595f7b8>

3D Structure for #<Metabolite:0x00007fed1595f7b8>