MiMeDB: Showing metabocard for Fructoselysine (MMDBc0030188)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:57:35 UTC

Update Date

2022-08-31 17:40:32 UTC

Metabolite ID

MMDBc0030188

Metabolite Identification

Common Name

Fructoselysine

Description

Fructoselysine 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 is invovled in Fructoselysine degradation. Escherichia coli was found to grow on fructoselysine as an energetic substrate at a rate of about one-third of that observed with glucose. (PMID:12147680 )

Structure

MOL SDF PDB SMILES InChI

Structure #1
  Mrv0541 02241207312D          

 21 21  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
   -1.4289    1.6500    0.0000 O   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
    0.7145    1.2375    0.0000 O   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 15  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 21  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  2  0  0  0  0
 11 14  1  0  0  0  0
 11 21  1  0  0  0  0
 12 19  2  0  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030188

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H22N2O7/c13-6(12(19)20)3-1-2-4-14-11-10(18)9(17)8(16)7(5-15)21-11/h6-9,11,14-17H,1-5,13H2,(H,19,20)

> <INCHI_KEY>
ZRMPOBPOYIGDMF-UHFFFAOYSA-N

> <FORMULA>
C12H22N2O7

> <MOLECULAR_WEIGHT>
306.3123

> <EXACT_MASS>
306.142701068

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.067970452928968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-4.465366138137584

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.235367226117447

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5822622893525926

> <JCHEM_PKA_STRONGEST_BASIC>
9.270726095092492

> <JCHEM_POLAR_SURFACE_AREA>
162.33999999999997

> <JCHEM_REFRACTIVITY>
69.57289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-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      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2   14                                                       
CONECT    5    7   15                                                       
CONECT    6    3   12   13                                                  
CONECT    7    5    8   21                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   14   21                                                  
CONECT   12    6   19   20                                                  
CONECT   13    6                                                            
CONECT   14    4   11                                                       
CONECT   15    5                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   12                                                            
CONECT   20   12                                                            
CONECT   21    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

Synonyms

Not Available

Molecular Formula

C₁₂H₂₂N₂O₇

Average Mass

306.3123

Monoisotopic Mass

306.142701068

IUPAC Name

2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid

Traditional Name

2-amino-6-{[4,5-dihydroxy-6-(hydroxymethyl)-3-oxooxan-2-yl]amino}hexanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H22N2O7/c13-6(12(19)20)3-1-2-4-14-11-10(18)9(17)8(16)7(5-15)21-11/h6-9,11,14-17H,1-5,13H2,(H,19,20)

InChI Key

ZRMPOBPOYIGDMF-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
Amino fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Monosaccharide
Oxane
Fatty acid
Fatty acyl
Ketone
Cyclic ketone
Amino acid
Secondary alcohol
Oxacycle
Carboxylic acid
Secondary aliphatic amine
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Secondary amine
Alcohol
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary alcohol
Primary amine
Carbonyl group
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	67.3 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-4.5	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.34 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	69.57 m³·mol⁻¹	ChemAxon
Polarizability	31.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	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_3_55) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08g4-1492000000-4787bf1070b0d9015d20	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uea-4940000000-b1b9e7534d1c743a8fa9	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-9610000000-9289451e9ffaf8102f66	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0934000000-92fe493cacc808bdce6a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4s-1930000000-6e8c2c673414bdb6d4fc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-059b-8900000000-96242a6e67a2a6a514b6	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

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

Fructoselysine

METLIN ID

Not Available

PubChem Compound

720

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 (MMDBc0030188)

MOL for #<Metabolite:0x00007fdb6d8748d0>

3D MOL for #<Metabolite:0x00007fdb6d8748d0>

3D SDF for #<Metabolite:0x00007fdb6d8748d0>

3D-SDF for #<Metabolite:0x00007fdb6d8748d0>

PDB for #<Metabolite:0x00007fdb6d8748d0>

3D PDB for #<Metabolite:0x00007fdb6d8748d0>

SMILES for #<Metabolite:0x00007fdb6d8748d0>

INCHI for #<Metabolite:0x00007fdb6d8748d0>

Structure for #<Metabolite:0x00007fdb6d8748d0>

3D Structure for #<Metabolite:0x00007fdb6d8748d0>