MiMeDB: Showing metabocard for 6-O-alpha-D-Glucopyranosyl-D-fructofuranose (MMDBc0000287)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-28 00:08:40 UTC

Update Date

2024-04-30 19:31:45 UTC

Metabolite ID

MMDBc0000287

Metabolite Identification

Common Name

6-O-alpha-D-Glucopyranosyl-D-fructofuranose

Description

isomaltulose belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. isomaltulose is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on isomaltulose.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310282001082D          

 23 24  0  0  1  0            999 V2000
   -6.4088   -2.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9239   -1.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1034   -1.6491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6184   -0.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980   -1.0679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3130   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    1.0206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4186    1.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    2.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1991    2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4541    3.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837    1.8053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2991    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8538    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -1.8216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6419   -1.9078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473   -2.4890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6118   -3.2427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7678   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2527   -3.0702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000287

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1O[C@H](OC[C@H]2OC(O)(CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12?/m1/s1

> <INCHI_KEY>
PVXPPJIGRGXGCY-TZLCEDOOSA-N

> <FORMULA>
C12H22O11

> <MOLECULAR_WEIGHT>
342.297

> <EXACT_MASS>
342.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.970997907005405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-3.23

> <JCHEM_LOGP>
-4.528834963666666

> <ALOGPS_LOGS>
0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.101606988230476

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.279238125855457

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322407

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
68.77409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.86e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palatinose

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-OCT-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-OCT-20         0                                  
HETATM    1  O   UNK     0     -11.963  -4.163   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -11.058  -2.917   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.526  -3.078   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.621  -1.832   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.090  -1.993   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.184  -0.748   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.811   0.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.906   1.905   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.381   3.370   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.136   4.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.166   5.419   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.105   5.419   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.581   6.884   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.890   3.370   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.425   3.846   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.366   1.905   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.460   0.659   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.463  -3.400   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.932  -3.561   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.368  -4.646   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.742  -6.053   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.900  -4.485   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.805  -5.731   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   14                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

Synonyms

Value	Source
6-O-alpha-D-Glucopyranosyl-D-fructose	ChEBI
6-O-alpha-D-Glucopyranosyl-D-fructofuranose	Kegg
6-O-a-D-Glucopyranosyl-D-fructose	Generator
6-O-Α-D-glucopyranosyl-D-fructose	Generator
6-O-a-D-Glucopyranosyl-D-fructofuranose	Generator
6-O-Α-D-glucopyranosyl-D-fructofuranose	Generator
D-Fructose, 6-O-alpha-D-glucopyranosyl-, monohydrate	HMDB
Isomaltulose anhydrous	HMDB
6-O alpha-D-Glucopyranosyl-D-fructose	HMDB
Isomaltulose monohydrate	HMDB
Isomaltulose	ChEBI

Molecular Formula

C₁₂H₂₂O₁₁

Average Mass

342.297

Monoisotopic Mass

342.116211528

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}oxane-3,4,5-triol

Traditional Name

palatinose

CAS Registry Number

13718-94-0

SMILES

OC[C@H]1O[C@H](OC[C@H]2OC(O)(CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12?/m1/s1

InChI Key

PVXPPJIGRGXGCY-TZLCEDOOSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
C-glycosyl compound
Oxane
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glycosylfructose (CHEBI:18394 )
Disaccharides (C01742 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	686 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-4.5	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.77 m³·mol⁻¹	ChemAxon
Polarizability	30.97 Å³	ChemAxon
Number of Rings	2	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_3_29) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	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
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva; Human supragingival plaque	Microbial culture

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

HMDB0341167

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isomaltulose

METLIN ID

Not Available

PubChem Compound

439559

PDB ID

Not Available

ChEBI ID

18394

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for 6-O-alpha-D-Glucopyranosyl-D-fructofuranose (MMDBc0000287)

MOL for #<Metabolite:0x00007fdb3c092b20>

3D MOL for #<Metabolite:0x00007fdb3c092b20>

3D SDF for #<Metabolite:0x00007fdb3c092b20>

3D-SDF for #<Metabolite:0x00007fdb3c092b20>

PDB for #<Metabolite:0x00007fdb3c092b20>

3D PDB for #<Metabolite:0x00007fdb3c092b20>

SMILES for #<Metabolite:0x00007fdb3c092b20>

INCHI for #<Metabolite:0x00007fdb3c092b20>

Structure for #<Metabolite:0x00007fdb3c092b20>

3D Structure for #<Metabolite:0x00007fdb3c092b20>