MiMeDB: Showing metabocard for Fructoselysine-6-phosphate (MMDBc0030189)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:57:41 UTC

Update Date

2022-08-31 17:40:32 UTC

Metabolite ID

MMDBc0030189

Metabolite Identification

Common Name

Fructoselysine-6-phosphate

Description

Fructoselysine-6-phosphate is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Fructoselysine-6-phosphate is invovled in Fructoselysine degradation. Fructoselysine-6-phosphate is involved in the metabolism of fructation product. The metabolism of the glycation product fructose-epsilon-lysine in Escherichia coli involves its ATP-dependent phosphorylation by a specific kinase (FrlD), followed by the conversion of fructoselysine 6-phosphate into glucose 6-phosphate and lysine by fructoselysine-6-phosphate deglycase (FrlB), which is distantly related to the isomerase domain of glucosamine-6-phosphate synthase. (PMID 16153181 )

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207312D          

 25 25  0  0  0  0            999 V2000
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 14  1  0  0  0  0
  5  7  1  0  0  0  0
  5 23  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7 24  1  0  0  0  0
  8  9  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  2  0  0  0  0
 11 14  1  0  0  0  0
 11 24  1  0  0  0  0
 12 18  2  0  0  0  0
 12 19  1  0  0  0  0
 20 25  1  0  0  0  0
 21 25  1  0  0  0  0
 22 25  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030189

> <DATABASE_NAME>
MIME

> <SMILES>
NC(CCCCNC1OC(COP(O)(O)=O)C(O)C(O)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H23N2O10P/c13-6(12(18)19)3-1-2-4-14-11-10(17)9(16)8(15)7(24-11)5-23-25(20,21)22/h6-9,11,14-16H,1-5,13H2,(H,18,19)(H2,20,21,22)

> <INCHI_KEY>
BZFCRRVQZCIOBA-UHFFFAOYSA-N

> <FORMULA>
C12H23N2O10P

> <MOLECULAR_WEIGHT>
386.2922

> <EXACT_MASS>
386.109031478

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
35.79874638193705

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-8.234657080621718

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.7400135780215589

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.0659791731653288

> <JCHEM_PKA_STRONGEST_BASIC>
9.317990399577262

> <JCHEM_POLAR_SURFACE_AREA>
208.86999999999995

> <JCHEM_REFRACTIVITY>
80.44579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      10.669   4.620   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.771   3.644   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.231   0.976   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      -4.001   2.310   0.000  0.00  0.00           P+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2   14                                                       
CONECT    5    7   23                                                       
CONECT    6    3   12   13                                                  
CONECT    7    5    8   24                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   14   24                                                  
CONECT   12    6   18   19                                                  
CONECT   13    6                                                            
CONECT   14    4   11                                                       
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   25                                                            
CONECT   21   25                                                            
CONECT   22   25                                                            
CONECT   23    5   25                                                       
CONECT   24    7   11                                                       
CONECT   25   20   21   22   23                                             
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

Synonyms

Value	Source
Fructoselysine-6-phosphoric acid	Generator

Molecular Formula

C₁₂H₂₃N₂O₁₀P

Average Mass

386.2922

Monoisotopic Mass

386.109031478

IUPAC Name

2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid

Traditional Name

2-amino-6-({4,5-dihydroxy-3-oxo-6-[(phosphonooxy)methyl]oxan-2-yl}amino)hexanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCCCNC1OC(COP(O)(O)=O)C(O)C(O)C1=O)C(O)=O

InChI Identifier

InChI=1S/C12H23N2O10P/c13-6(12(18)19)3-1-2-4-14-11-10(17)9(16)8(15)7(24-11)5-23-25(20,21)22/h6-9,11,14-16H,1-5,13H2,(H,18,19)(H2,20,21,22)

InChI Key

BZFCRRVQZCIOBA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Medium-chain fatty acid
Hydroxy fatty acid
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Fatty acid
Fatty acyl
Amino acid
Cyclic ketone
Ketone
1,2-diol
Secondary alcohol
Secondary amine
Organoheterocyclic compound
Secondary aliphatic amine
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxide
Alcohol
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Primary amine
Organopnictogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.16 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-8.2	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.07	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	208.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	80.45 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_82) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ku-1329000000-45bc525596d4fe9c5a69	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7n-5923000000-f3fd3f8e42b8567c1eb6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-7920000000-dab81d34a57b60e30437	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-5916000000-0f9797f9fc948edd0c14	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9510000000-b68cbc30b57ea1b0f23e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9ee8e58b2ff830436867	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

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

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

721

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Fructoselysine-6-phosphate (MMDBc0030189)

MOL for #<Metabolite:0x00007feca44f57e8>

3D MOL for #<Metabolite:0x00007feca44f57e8>

3D SDF for #<Metabolite:0x00007feca44f57e8>

3D-SDF for #<Metabolite:0x00007feca44f57e8>

PDB for #<Metabolite:0x00007feca44f57e8>

3D PDB for #<Metabolite:0x00007feca44f57e8>

SMILES for #<Metabolite:0x00007feca44f57e8>

INCHI for #<Metabolite:0x00007feca44f57e8>

Structure for #<Metabolite:0x00007feca44f57e8>

3D Structure for #<Metabolite:0x00007feca44f57e8>