MiMeDB: Showing metabocard for N(6)-(6-phospho-D-fructosyl)-L-lysine (MMDBc0056193)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:19:09 UTC

Update Date

2022-08-12 20:09:37 UTC

Metabolite ID

MMDBc0056193

Metabolite Identification

Common Name

N(6)-(6-phospho-D-fructosyl)-L-lysine

Description

fructoselysine 6-phosphate(1-), also known as fructose L-lysine-6-phosphoric acid, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Based on a literature review very few articles have been published on fructoselysine 6-phosphate(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222192D          

 29 28  0  0  1  0            999 V2000
    7.4763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6197    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0974    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 13  1  1  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  2  0  0  0  0
  9 16  1  6  0  0  0
 10 17  1  1  0  0  0
 11 18  1  1  0  0  0
 19 12  2  0  0  0  0
 20 12  1  0  0  0  0
 24  6  1  0  0  0  0
 25 21  1  0  0  0  0
 25 22  1  0  0  0  0
 25 23  2  0  0  0  0
 25 24  1  0  0  0  0
  7 26  1  1  0  0  0
  9 27  1  6  0  0  0
 10 28  1  1  0  0  0
 11 29  1  1  0  0  0
M  CHG  1  20  -1
M  END


  Mrv1652306172222192D          

 29 28  0  0  1  0            999 V2000
    7.4763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6197    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0974    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
  7 13  1  1  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  2  0  0  0  0
  9 16  1  6  0  0  0
 10 17  1  1  0  0  0
 11 18  1  1  0  0  0
 19 12  2  0  0  0  0
 20 12  1  0  0  0  0
 24  6  1  0  0  0  0
 25 21  1  0  0  0  0
 25 22  1  0  0  0  0
 25 23  2  0  0  0  0
 25 24  1  0  0  0  0
  7 26  1  1  0  0  0
  9 27  1  6  0  0  0
 10 28  1  1  0  0  0
 11 29  1  1  0  0  0
M  CHG  1  20  -1
M  END
> <DATABASE_ID>
MMDBc0056193

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCCCNCC(=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)COP(O)(O)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H25N2O10P/c13-7(12(19)20)3-1-2-4-14-5-8(15)10(17)11(18)9(16)6-24-25(21,22)23/h7,9-11,14,16-18H,1-6,13H2,(H,19,20)(H2,21,22,23)/p-1/t7-,9+,10+,11+/m0/s1

> <INCHI_KEY>
ZICZRZZPXBCXCE-AYHFEMFVSA-M

> <FORMULA>
C12H24N2O10P

> <MOLECULAR_WEIGHT>
387.302

> <EXACT_MASS>
387.117405559

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.356119829331945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]amino}hexanoate

> <JCHEM_LOGP>
-8.869852767779419

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.3133059299954817

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4201209554931102

> <JCHEM_PKA_STRONGEST_BASIC>
9.347497432191046

> <JCHEM_POLAR_SURFACE_AREA>
222.69999999999996

> <JCHEM_REFRACTIVITY>
93.59459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]amino}hexanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      13.956   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.622   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.289   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.623   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.957   2.667   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      16.623   4.977   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       9.955   2.667   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.286   4.977   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      19.290   3.437   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      17.957   1.127   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0      -2.048   1.897   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.485   4.001   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.055   1.334   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.619   3.437   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      -0.715   2.667   0.000  0.00  0.00           P+0
HETATM   26  H   UNK     0      16.623   1.897   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.286   1.897   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.954   1.897   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.620   4.207   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2   14                                                       
CONECT    5    8   14                                                       
CONECT    6    9   24                                                       
CONECT    7    3   12   13   26                                             
CONECT    8    5   10   15                                                  
CONECT    9    6   11   16   27                                             
CONECT   10    8   11   17   28                                             
CONECT   11    9   10   18   29                                             
CONECT   12    7   19   20                                                  
CONECT   13    7                                                            
CONECT   14    4    5                                                       
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   12                                                            
CONECT   21   25                                                            
CONECT   22   25                                                            
CONECT   23   25                                                            
CONECT   24    6   25                                                       
CONECT   25   21   22   23   24                                             
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   56    0
END

Synonyms

Value	Source
(2S)-2-Ammonio-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonatooxy)hexyl]ammonio}hexanoate	ChEBI
Fructose L-lysine-6-phosphate	ChEBI
Fructosyllysine 6-phosphate(1-)	ChEBI
N(6)-(6-Phospho-D-fructosyl)-L-lysine	ChEBI
(2S)-2-Ammonio-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonatooxy)hexyl]ammonio}hexanoic acid	Generator
Fructose L-lysine-6-phosphoric acid	Generator
Fructosyllysine 6-phosphoric acid(1-)	Generator
Fructoselysine 6-phosphoric acid(1-)	Generator

Molecular Formula

C₁₂H₂₄N₂O₁₀P

Average Mass

387.302

Monoisotopic Mass

387.117405559

IUPAC Name

(2S)-2-amino-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]amino}hexanoate

Traditional Name

(2S)-2-amino-6-{[(3S,4R,5R)-3,4,5-trihydroxy-2-oxo-6-(phosphonooxy)hexyl]amino}hexanoate

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCCCNCC(=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)COP(O)(O)=O)C([O-])=O

InChI Identifier

InChI=1S/C12H25N2O10P/c13-7(12(19)20)3-1-2-4-14-5-8(15)10(17)11(18)9(16)6-24-25(21,22)23/h7,9-11,14,16-18H,1-6,13H2,(H,19,20)(H2,21,22,23)/p-1/t7-,9+,10+,11+/m0/s1

InChI Key

ZICZRZZPXBCXCE-AYHFEMFVSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Alpha-amino acid
Alpha-amino acid or derivatives
Monosaccharide phosphate
L-alpha-amino acid
Medium-chain fatty acid
Hydroxy fatty acid
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acid
Fatty acyl
Alpha-aminoketone
Alpha-hydroxy ketone
1,3-aminoalcohol
Secondary alcohol
Amino acid or derivatives
Carboxylic acid salt
Amino acid
Ketone
Secondary amine
Polyol
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Organic salt
Carbonyl group
Organonitrogen compound
Amine
Organopnictogen compound
Primary amine
Alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Primary aliphatic amine
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:61392 )
L-alpha-amino acid anion (CHEBI:61392 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-8.9	ChemAxon
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	9.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	222.7 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	93.59 m³·mol⁻¹	ChemAxon
Polarizability	35.36 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

Spectra

Not Available

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
Bacteria	Proteobacteria	3	Human ; Human feces

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26332215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50909832

PDB ID

Not Available

ChEBI ID

61392

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)-(6-phospho-D-fructosyl)-L-lysine (MMDBc0056193)

MOL for #<Metabolite:0x00007fed080c02e0>

3D MOL for #<Metabolite:0x00007fed080c02e0>

3D SDF for #<Metabolite:0x00007fed080c02e0>

3D-SDF for #<Metabolite:0x00007fed080c02e0>

PDB for #<Metabolite:0x00007fed080c02e0>

3D PDB for #<Metabolite:0x00007fed080c02e0>

SMILES for #<Metabolite:0x00007fed080c02e0>

INCHI for #<Metabolite:0x00007fed080c02e0>

Structure for #<Metabolite:0x00007fed080c02e0>

3D Structure for #<Metabolite:0x00007fed080c02e0>