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Showing NP-Card for β-d-fructopyranose (NP0215074)

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Record Information
Version1.0
Created at2022-09-05 14:32:56 UTC
Updated at2022-09-05 14:32:57 UTC
NP-MRD IDNP0215074
Secondary Accession NumbersNone
Natural Product Identification
Common Nameβ-d-fructopyranose
DescriptionBeta-D-fructopyranose belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. A D-fructopyranose in which the anomeric centre has beta-configuration. β-d-fructopyranose is found in Centaurea jacea. It was first documented in 2002 (PMID: 12477047). Beta-D-fructopyranose is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16038890) (PMID: 20852065).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0215074 (β-d-fructopyranose)


  Mrv1652305062021432D          

 12 12  0  0  1  0            999 V2000
    4.2365   -0.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -1.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -0.4294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    0.8081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    1.2206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365    0.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -1.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  7  2  1  1  0  0  0
  8  3  1  1  0  0  0
  9  4  1  6  0  0  0
 10  5  1  6  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0215074 (β-d-fructopyranose)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    2.1771    1.4476   -0.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335    0.2407   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9747   -0.2007    0.4200 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1759   -1.3985    1.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5460    0.7750    1.2819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    0.5204    1.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6757    0.6197    0.5676 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3548    1.7521   -0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398   -0.6041   -0.2968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2430   -0.7838   -1.3105 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785   -0.3991   -0.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5382   -1.5400   -1.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    1.9861   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0666    0.4048    0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7068   -0.4984   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -2.1340    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    1.1462    2.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403   -0.5437    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7234    0.6287    0.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476    2.1543   -0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3301   -1.4643    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -0.5057   -2.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402    0.5101   -1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2490   -2.1134   -1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  1
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  6
 12 24  1  0
M  END
Download

3D SDF for NP0215074 (β-d-fructopyranose)


  Mrv1652305062021432D          

 12 12  0  0  1  0            999 V2000
    4.2365   -0.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9345   -1.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.2206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -0.4294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075    0.8081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    1.2206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365    0.8081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1095   -1.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  7  2  1  1  0  0  0
  8  3  1  1  0  0  0
  9  4  1  6  0  0  0
 10  5  1  6  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215074

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1

> <INCHI_KEY>
LKDRXBCSQODPBY-ARQDHWQXSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.052977710814297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

> <ALOGPS_LOGP>
-2.51

> <JCHEM_LOGP>
-2.7579993179999995

> <ALOGPS_LOGS>
0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.643871080491373

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.291030669254255

> <JCHEM_PKA_STRONGEST_BASIC>
-3.450704169945884

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
36.3608

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-D-fructopyranose

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0215074 (β-d-fructopyranose)

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PDB for NP0215074 (β-d-fructopyranose)
HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  O   UNK     0       7.908  -0.032   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907  -0.802   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.344  -2.135   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.907   2.278   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.574   3.818   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       6.574  -3.469   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.241  -0.032   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -0.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241   1.508   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574   2.278   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   1.508   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.804  -2.135   0.000  0.00  0.00           C+0
CONECT    1    8   11                                                       
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    9                                                            
CONECT    5   10                                                            
CONECT    6   12                                                            
CONECT    7    2    8    9                                                  
CONECT    8    1    3    7   12                                             
CONECT    9    4    7   10                                                  
CONECT   10    5    9   11                                                  
CONECT   11    1   10                                                       
CONECT   12    6    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0215074 (β-d-fructopyranose)
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SMILES for NP0215074 (β-d-fructopyranose)
OC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
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INCHI for NP0215074 (β-d-fructopyranose)
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1
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View in JSmol
Synonyms
ValueSource
b-D-FructopyranoseGenerator
Β-D-fructopyranoseGenerator
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameβ-D-fructopyranose
CAS Registry NumberNot Available
SMILES
OC[C@@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1
InChI KeyLKDRXBCSQODPBY-ARQDHWQXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Centaurea jaceaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentMonosaccharides  
Alternative Parents
Substituents
  • Oxane
    • 

  • Monosaccharide
    • 

  • Secondary alcohol
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24310  
PDB IDNot Available
ChEBI ID41005  
Good Scents IDNot Available
References
General References
  1. Benbrahim N, Sekkal-Rahal M, Vergoten G: Harmonic dynamics of beta-D-fructopyranose. Spectrochim Acta A Mol Biomol Spectrosc. 2002 Nov;58(13):3021-31. doi:  10.1016/s1386-1425(02)00098-7. [PubMed:12477047  ] 
  2. Costa MT: QM/MM study of D-fructose in aqueous solution. Carbohydr Res. 2005 Sep 26;340(13):2185-94. doi: 10.1016/j.carres.2005.06.020. [PubMed:16038890  ] 
  3. Doores KJ, Fulton Z, Hong V, Patel MK, Scanlan CN, Wormald MR, Finn MG, Burton DR, Wilson IA, Davis BG: A nonself sugar mimic of the HIV glycan shield shows enhanced antigenicity. Proc Natl Acad Sci U S A. 2010 Oct 5;107(40):17107-12. doi:  10.1073/pnas.1002717107. Epub 2010 Sep 17. [PubMed:20852065  ] 
  4. LOTUS database [Link]