NP-MRD: Showing NP-Card for Palatinose (NP0333353)

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Record Information

Version

2.0

Created at

2024-06-03 19:55:57 UTC

Updated at

2024-09-03 04:22:02 UTC

NP-MRD ID

NP0333353

Natural Product DOI

https://doi.org/10.57994/2717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Palatinose

Description

6-O-alpha-D-glucopyranosyl-D-fructofuranose, also known as 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. Palatinose was first documented in 2007 (PMID: 17548953). 6-O-alpha-D-glucopyranosyl-D-fructofuranose is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 21895946) (PMID: 22133441) (PMID: 22264450) (PMID: 24866943).

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>
NP0333353

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

Synonyms

Value	Source
6-O-alpha-D-Glucopyranosyl-D-fructose	ChEBI
Isomaltulose	ChEBI
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	MeSH
Isomaltulose anhydrous	MeSH
6-O alpha-D-Glucopyranosyl-D-fructose	MeSH
Isomaltulose monohydrate	MeSH

Chemical Formula

C₁₂H₂₂O₁₁

Average Mass

342.2970 Da

Monoisotopic Mass

342.11621 Da

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

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D2O, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, D₂O, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-03	View Spectrum

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

388649

KEGG Compound ID

C01742

BioCyc ID

CPD-230

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439559

PDB ID

Not Available

ChEBI ID

18394

Good Scents ID

Not Available

References

General References

Oizumi T, Daimon M, Jimbu Y, Kameda W, Arawaka N, Yamaguchi H, Ohnuma H, Sasaki H, Kato T: A palatinose-based balanced formula improves glucose tolerance, serum free fatty acid levels and body fat composition. Tohoku J Exp Med. 2007 Jun;212(2):91-9. doi: 10.1620/tjem.212.91. [PubMed:17548953 ]
Basnayake SW, Morgan TC, Wu L, Birch RG: Field performance of transgenic sugarcane expressing isomaltulose synthase. Plant Biotechnol J. 2012 Feb;10(2):217-25. doi: 10.1111/j.1467-7652.2011.00655.x. Epub 2011 Sep 5. [PubMed:21895946 ]
Goulter KC, Hashimi SM, Birch RG: Microbial sucrose isomerases: producing organisms, genes and enzymes. Enzyme Microb Technol. 2012 Jan 5;50(1):57-64. doi: 10.1016/j.enzmictec.2011.09.011. Epub 2011 Oct 5. [PubMed:22133441 ]
Konig D, Theis S, Kozianowski G, Berg A: Postprandial substrate use in overweight subjects with the metabolic syndrome after isomaltulose (Palatinose) ingestion. Nutrition. 2012 Jun;28(6):651-6. doi: 10.1016/j.nut.2011.09.019. Epub 2012 Jan 21. [PubMed:22264450 ]
Mu W, Li W, Wang X, Zhang T, Jiang B: Current studies on sucrose isomerase and biological isomaltulose production using sucrose isomerase. Appl Microbiol Biotechnol. 2014 Aug;98(15):6569-82. doi: 10.1007/s00253-014-5816-2. Epub 2014 May 28. [PubMed:24866943 ]

Showing NP-Card for Palatinose (NP0333353)

MOL for NP0333353 (Palatinose)

3D MOL for NP0333353 (Palatinose)

3D SDF for NP0333353 (Palatinose)

3D-SDF for NP0333353 (Palatinose)

PDB for NP0333353 (Palatinose)

3D PDB for NP0333353 (Palatinose)

SMILES for NP0333353 (Palatinose)

INCHI for NP0333353 (Palatinose)

Structure for NP0333353 (Palatinose)

3D Structure for NP0333353 (Palatinose)