MiMeDB: Showing metabocard for 6-deoxy-6-sulfoglucono-1,5-lactone (MMDBc0032885)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 22:56:19 UTC

Update Date

2022-08-31 21:45:07 UTC

Metabolite ID

MMDBc0032885

Metabolite Identification

Common Name

6-deoxy-6-sulfoglucono-1,5-lactone

Description

A carbohydrate sulfonate that is D-glucono-1,5-lactone in which the 6-hydroxy group is replaced by a sulfo group.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311182123562D          

 15 15  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    1.4289   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032885

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O8S/c7-3-2(1-15(11,12)13)14-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H,11,12,13)/t2-,3-,4+,5-/m1/s1

> <INCHI_KEY>
YOMAOVCVRGQULE-SQOUGZDYSA-N

> <FORMULA>
C6H10O8S

> <MOLECULAR_WEIGHT>
242.2

> <EXACT_MASS>
242.009638456

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.74640831540941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methanesulfonic acid

> <ALOGPS_LOGP>
-2.04

> <JCHEM_LOGP>
-3.034880468666667

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.621712058345267

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4020664407646501

> <JCHEM_PKA_STRONGEST_BASIC>
-3.650934706724297

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
43.1728

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-21         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.897  -4.414   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.437  -1.746   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    6   13   15                                                  
CONECT   13   12    1   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

Synonyms

Value	Source
[(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-oxooxan-2-yl]methanesulfonic acid	ChEBI
[(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-oxooxan-2-yl]methanesulfonate	Generator
[(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-oxooxan-2-yl]methanesulphonate	Generator
[(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-oxooxan-2-yl]methanesulphonic acid	Generator
6-Deoxy-6-sulphoglucono-1,5-lactone	Generator

Molecular Formula

C₆H₁₀O₈S

Average Mass

242.2

Monoisotopic Mass

242.009638456

IUPAC Name

[(2S,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methanesulfonic acid

Traditional Name

[(2S,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H10O8S/c7-3-2(1-15(11,12)13)14-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H,11,12,13)/t2-,3-,4+,5-/m1/s1

InChI Key

YOMAOVCVRGQULE-SQOUGZDYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Gluconolactones

Alternative Parents

Substituents

Gluconolactone
Delta valerolactone
Delta_valerolactone
Oxane
Alkanesulfonic acid
Sulfonyl
Organosulfonic acid
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Alcohol
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	189 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.17 m³·mol⁻¹	ChemAxon
Polarizability	19.75 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_3_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	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

Not Available

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 sputum; Human subgingival plaque; Human feces	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

58145710

KEGG Compound ID

Not Available

BioCyc ID

CPD-18481

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92136126

PDB ID

Not Available

ChEBI ID

88250

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Huang W, Brewer LK, Jones JW, Nguyen AT, Marcu A, Wishart DS, Oglesby-Sherrouse AG, Kane MA, Wilks A: PAMDB: a comprehensive Pseudomonas aeruginosa metabolome database. Nucleic Acids Res. 2018 Jan 4;46(D1):D575-D580. doi: 10.1093/nar/gkx1061. [PubMed:29106626 ]

Showing metabocard for 6-deoxy-6-sulfoglucono-1,5-lactone (MMDBc0032885)

MOL for #<Metabolite:0x00007fecb0efa138>

3D MOL for #<Metabolite:0x00007fecb0efa138>

3D SDF for #<Metabolite:0x00007fecb0efa138>

3D-SDF for #<Metabolite:0x00007fecb0efa138>

PDB for #<Metabolite:0x00007fecb0efa138>

3D PDB for #<Metabolite:0x00007fecb0efa138>

SMILES for #<Metabolite:0x00007fecb0efa138>

INCHI for #<Metabolite:0x00007fecb0efa138>

Structure for #<Metabolite:0x00007fecb0efa138>

3D Structure for #<Metabolite:0x00007fecb0efa138>