MiMeDB: Showing metabocard for 6-Deoxy-6-sulfo-D-fructose (MMDBc0031953)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:56:21 UTC

Update Date

2022-08-31 18:26:46 UTC

Metabolite ID

MMDBc0031953

Metabolite Identification

Common Name

6-Deoxy-6-sulfo-D-fructose

Description

6-Deoxy-6-sulfo-D-fructose is an intermediate in sulfoglycolysis pathway in E.coli. It is a product for the enzyme sulfoquinovose isomerase which catalyzes the reaction sulfoquinovose -> 6-deoxy-6-sulfo-D-fructose. It is also the substrate for the enzyme 6-deoxy-6-sulfofructose kinase which catalyzes the reaction 6-deoxy-6-sulfo-D-fructose + ATP -> 6-deoxy-6-sulfo-D-fructose 1-phosphate + ADP + H+ (BioCyc compound: CPD-16501).

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533007211515422D          
 
 15 15  0  0  1  0            999 V2000
    9.6525   -8.6212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4775   -8.6212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7324   -7.8366    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   10.0650   -7.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3976   -7.8366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6200   -7.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9624   -9.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1676   -9.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4469   -8.2491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3158   -7.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -7.5839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -6.7589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9700   -7.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7950   -8.4089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1019   -7.4641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  1  0  0  0
  2  7  1  1  0  0  0
  1  8  1  6  0  0  0
  3  9  1  4  0  0  0
  3 10  1  4  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031953

> <DATABASE_NAME>
MIME

> <SMILES>
OCC1(O)O[C@H](CS(O)(=O)=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O8S/c7-2-6(10)5(9)4(8)3(14-6)1-15(11,12)13/h3-5,7-10H,1-2H2,(H,11,12,13)/t3-,4-,5+,6?/m1/s1

> <INCHI_KEY>
QTQNAYQDKCBJTC-VRPWFDPXSA-N

> <FORMULA>
C6H12O8S

> <MOLECULAR_WEIGHT>
244.21

> <EXACT_MASS>
244.02528852

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.44671340728264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methanesulfonic acid

> <ALOGPS_LOGP>
-2.15

> <JCHEM_LOGP>
-3.0476066006666667

> <ALOGPS_LOGS>
0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.285950998820272

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2987775980959233

> <JCHEM_PKA_STRONGEST_BASIC>
-3.450942600090407

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
44.754799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  C   UNK     0      18.018 -16.093   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.558 -16.093   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.034 -14.628   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.788 -13.723   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      17.542 -14.628   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.091 -14.157   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      20.463 -17.339   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      17.113 -17.339   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.368 -15.398   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      21.123 -13.539   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0      14.551 -14.157   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0      14.551 -12.617   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      13.011 -14.157   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      14.551 -15.697   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      22.590 -13.933   0.000  0.00  0.00           O+0
CONECT    1    2    5    8                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9   10                                             
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5   11                                                       
CONECT    7    2                                                            
CONECT    8    1                                                            
CONECT    9    3                                                            
CONECT   10    3   15                                                       
CONECT   11    6   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
6-Deoxy-6-sulfofructose	ChEBI
6-Deoxy-6-sulphofructose	ChEBI
6-Sulfofructose	ChEBI
6-Sulphofructose	Generator
6-Deoxy-6-sulphO-D-fructose	Generator
6-Deoxy-6-sulphO-D-fructofuranose	Generator

Molecular Formula

C₆H₁₂O₈S

Average Mass

244.21

Monoisotopic Mass

244.02528852

IUPAC Name

[(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methanesulfonic acid

Traditional Name

[(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methanesulfonic acid

CAS Registry Number

Not Available

SMILES

OCC1(O)O[C@H](CS(O)(=O)=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H12O8S/c7-2-6(10)5(9)4(8)3(14-6)1-15(11,12)13/h3-5,7-10H,1-2H2,(H,11,12,13)/t3-,4-,5+,6?/m1/s1

InChI Key

QTQNAYQDKCBJTC-VRPWFDPXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Sugar acid
Monosaccharide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Tetrahydrofuran
Alkanesulfonic acid
Secondary alcohol
Hemiacetal
Organoheterocyclic compound
Polyol
Oxacycle
Primary alcohol
Alcohol
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate sulfonate (CHEBI:77261 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	264 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.75 m³·mol⁻¹	ChemAxon
Polarizability	20.45 Å³	ChemAxon
Number of Rings	1	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0490000000-713d63705b3edf337aa5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-4930000000-9d5ca9ec17d8c1e30949	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059i-7900000000-2280ef84f4e7636f9f4d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9230000000-82863d61f3827a6e52a5	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9110000000-a72e917710475b5b8ef4	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9400000000-700c0cec7ac992fdaa38	2015-09-15	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	2	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

CPD-16501

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

77261

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 6-Deoxy-6-sulfo-D-fructose (MMDBc0031953)

MOL for #<Metabolite:0x0000556b6aea7358>

3D MOL for #<Metabolite:0x0000556b6aea7358>

3D SDF for #<Metabolite:0x0000556b6aea7358>

3D-SDF for #<Metabolite:0x0000556b6aea7358>

PDB for #<Metabolite:0x0000556b6aea7358>

3D PDB for #<Metabolite:0x0000556b6aea7358>

SMILES for #<Metabolite:0x0000556b6aea7358>

INCHI for #<Metabolite:0x0000556b6aea7358>

Structure for #<Metabolite:0x0000556b6aea7358>

3D Structure for #<Metabolite:0x0000556b6aea7358>