NP-MRD: Showing NP-Card for 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol (NP0221239)

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Record Information

Version

2.0

Created at

2022-09-05 22:45:27 UTC

Updated at

2022-09-05 22:45:27 UTC

NP-MRD ID

NP0221239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

Description

Neokestose, also known as 6g-kestotriose, belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Neokestose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Neokestose has been detected, but not quantified in, several different foods, such as cereals and cereal products, common wheats, french plantains, and garden onions. 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol is found in Acer saccharum and Asparagus cochinchinensis. 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol was first documented in 2003 (PMID: 15296187). This could make neokestose a potential biomarker for the consumption of these foods (PMID: 19860446) (PMID: 22511773) (PMID: 16295657) (PMID: 22297043).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061304552D          

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M  END

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  Mrv0541 05061304552D          

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M  END
> <DATABASE_ID>
NP0221239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(CO)(OCC2OC(OC3(CO)OC(CO)C(O)C3O)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O16/c19-1-6-10(24)14(28)17(4-21,32-6)30-3-8-9(23)12(26)13(27)16(31-8)34-18(5-22)15(29)11(25)7(2-20)33-18/h6-16,19-29H,1-5H2

> <INCHI_KEY>
HQFMTRMPFIZQJF-UHFFFAOYSA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.4371

> <EXACT_MASS>
504.169034976

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
46.44084226363342

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-3.22

> <JCHEM_LOGP>
-6.125130709333333

> <ALOGPS_LOGS>
0.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.113945453991244

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.654707164441886

> <JCHEM_PKA_STRONGEST_BASIC>
-3.455826066052418

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
101.62480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.747  -6.632   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.297   9.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.518  -0.407   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.103  -1.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.652   4.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.842  -5.386   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.392   8.326   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.487   0.738   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.019   0.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.302  -5.386   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.148   8.326   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.050   1.562   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.574   3.026   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.826  -3.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.624   6.861   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.933   3.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.072  -3.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.378   5.956   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.121  -8.038   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.671  10.978   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.609  -2.192   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.159   5.131   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.495  -1.047   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.397  -6.632   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.053   9.572   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.556   1.242   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.604   4.171   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.362  -3.445   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.089   6.385   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.042  -1.872   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.963   2.202   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.318  -3.921   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.868   6.861   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.408   4.811   0.000  0.00  0.00           O+0
CONECT    1    6   19                                                       
CONECT    2    7   20                                                       
CONECT    3    8   30                                                       
CONECT    4   17   21                                                       
CONECT    5   18   22                                                       
CONECT    6    1   10   32                                                  
CONECT    7    2   11   33                                                  
CONECT    8    3    9   31                                                  
CONECT    9    8   12   23                                                  
CONECT   10    6   14   24                                                  
CONECT   11    7   15   25                                                  
CONECT   12    9   13   26                                                  
CONECT   13   12   16   27                                                  
CONECT   14   10   17   28                                                  
CONECT   15   11   18   29                                                  
CONECT   16   13   31   34                                                  
CONECT   17    4   14   30   32                                             
CONECT   18    5   15   33   34                                             
CONECT   19    1                                                            
CONECT   20    2                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30    3   17                                                       
CONECT   31    8   16                                                       
CONECT   32    6   17                                                       
CONECT   33    7   18                                                       
CONECT   34   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
6g-Kestotriose	HMDB
b-D-Fructofuranosyl 6-O-b-D-fructofuranosyl-a-D-glucopyranoside, 8ci	HMDB
Neo-kestose	HMDB
O-b-D-Fructofuranosyl-(2->6)-a-D-glucopyranosyl b-D-fructofuranoside	HMDB
Neokestose	MeSH

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4371 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCC1OC(CO)(OCC2OC(OC3(CO)OC(CO)C(O)C3O)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1S/C18H32O16/c19-1-6-10(24)14(28)17(4-21,32-6)30-3-8-9(23)12(26)13(27)16(31-8)34-18(5-22)15(29)11(25)7(2-20)33-18/h6-16,19-29H,1-5H2

InChI Key

HQFMTRMPFIZQJF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acer saccharum	LOTUS Database	35616633
Asparagus cochinchinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Tetrahydrofuran
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a fructan (6G-KESTOTETRAOSE )

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	-6.1	ChemAxon
logS	0.08	ALOGPS
pKa (Strongest Acidic)	11.65	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	268.68 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	46.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0029921

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001178

KNApSAcK ID

Not Available

Chemspider ID

92512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Der Agopian RG, Purgatto E, Cordenunsi BR, Lajolo FM: Synthesis of fructooligosaccharides in banana 'prata' and its relation to invertase activity and sucrose accumulation. J Agric Food Chem. 2009 Nov 25;57(22):10765-71. doi: 10.1021/jf902163f. [PubMed:19860446 ]
Alvaro-Benito M, Sainz-Polo MA, Gonzalez-Perez D, Gonzalez B, Plou FJ, Fernandez-Lobato M, Sanz-Aparicio J: Structural and kinetic insights reveal that the amino acid pair Gln-228/Asn-254 modulates the transfructosylating specificity of Schwanniomyces occidentalis beta-fructofuranosidase, an enzyme that produces prebiotics. J Biol Chem. 2012 Jun 1;287(23):19674-86. doi: 10.1074/jbc.M112.355503. Epub 2012 Apr 16. [PubMed:22511773 ]
Bekers M, Upite D, Kaminska E, Laukevics J, Ionina R, Vigants A: Catalytic activity of zymomonas mobilis extracellular "levan-levansucrase" complex in sucrose medium. Commun Agric Appl Biol Sci. 2003;68(2 Pt A):321-4. [PubMed:15296187 ]
Flieger M, Kantorova M, Halada P, Kuzma M, Pazoutova S, Stodulkova E, Kolinska R: Oligosaccharides produced by submerged cultures of Claviceps africana and Claviceps sorghi. Folia Microbiol (Praha). 2005;50(3):198-204. doi: 10.1007/BF02931566. [PubMed:16295657 ]
Linde D, Rodriguez-Colinas B, Estevez M, Poveda A, Plou FJ, Fernandez Lobato M: Analysis of neofructooligosaccharides production mediated by the extracellular beta-fructofuranosidase from Xanthophyllomyces dendrorhous. Bioresour Technol. 2012 Apr;109:123-30. doi: 10.1016/j.biortech.2012.01.023. Epub 2012 Jan 14. [PubMed:22297043 ]
LOTUS database [Link]

Showing NP-Card for 2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol (NP0221239)

MOL for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D MOL for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D SDF for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D-SDF for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

PDB for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D PDB for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

SMILES for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

INCHI for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

Structure for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)

3D Structure for NP0221239 (2-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-3,4,5-triol)