Np mrd loader

Showing NP-Card for (2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol (NP0202844)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-04 22:09:27 UTC
Updated at2022-09-04 22:09:27 UTC
NP-MRD IDNP0202844
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
DescriptionAlpha-D-talopyranose, also known as α-D-talose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. (2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol is found in Catharanthus roseus, Marsdenia tomentosa, Paeonia peregrina and Piper retrofractum. (2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol was first documented in 2000 (PMID: 10819976). Based on a literature review a small amount of articles have been published on alpha-D-talopyranose (PMID: 17049912) (PMID: 33445012).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)


  Mrv1652309052200092D          

 12 12  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  1  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
  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
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
Download

3D MOL for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
    3.0430    0.6165   -1.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1945   -0.3672   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765    0.3615    0.0671 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4179    1.2542   -0.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255    0.7365   -1.1968 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3715    1.7980   -1.8672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7189    0.2318   -0.1659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367   -1.0975   -0.5276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724    0.2092    1.1668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7094   -0.3482    2.1759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3113   -0.5835    0.8754 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0063   -1.6669    0.0617 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4391    1.0975   -0.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.0226   -0.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408   -0.9220   -1.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613    0.9570    0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146   -0.0175   -1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6580    2.4229   -1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6057    0.8592   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5541   -1.5502    0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6858    1.2791    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1758   -0.8175    2.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7919   -0.8916    1.8255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0545   -2.5389    0.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  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
  3 16  1  1
  5 17  1  6
  6 18  1  0
  7 19  1  1
  8 20  1  0
  9 21  1  1
 10 22  1  0
 11 23  1  1
 12 24  1  0
M  END
Download

3D SDF for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)


  Mrv1652309052200092D          

 12 12  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
    0.0000    0.0000    0.0000 C   0  0  1  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
    0.0000    0.8250    0.0000 C   0  0  1  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
  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
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0202844

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5+,6+/m1/s1

> <INCHI_KEY>
WQZGKKKJIJFFOK-URLGYRAOSA-N

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.156

> <EXACT_MASS>
180.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.034256352871346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

> <JCHEM_LOGP>
-2.932539218

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.687538461190869

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.298101552080594

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810792051782764

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
35.923399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)

Download
PDB for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Download
3D PDB for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)
Download
SMILES for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)
OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@H]1O
Download
INCHI for NP0202844 ((2s,3s,4s,5r,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol)
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5+,6+/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(2S,3S,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrolChEBI
alpha-D-TaloseChEBI
WURCS=2.0/1,1,0/[a1112h-1a_1-5]/1/ChEBI
a-D-TaloseGenerator
Α-D-taloseGenerator
a-D-TalopyranoseGenerator
Α-D-talopyranoseGenerator
Chemical FormulaC6H12O6
Average Mass180.1560 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2S,3S,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Name(2S,3S,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5+,6+/m1/s1
InChI KeyWQZGKKKJIJFFOK-URLGYRAOSA-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
Catharanthus roseusLOTUS Database
Marsdenia tomentosaLOTUS Database
Paeonia peregrinaLOTUS Database
Piper retrofractumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentHexoses  
Alternative Parents
Substituents
  • Hexose monosaccharide
    • 

  • Oxane
    • 

  • Secondary alcohol
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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-2.9ChemAxon
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.03 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 ID73715  
KEGG Compound IDNot Available
BioCyc IDAlpha-D-Talose  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound81696  
PDB IDNot Available
ChEBI ID141392  
Good Scents IDNot Available
References
General References
  1. Reguieg C, Yousfi N, Sekkal-Rahal M: Normal coordinates analyses of beta-D-allose and alpha-D-talose in the crystalline state. Spectrochim Acta A Mol Biomol Spectrosc. 2007 Jul;67(3-4):966-75. doi: 10.1016/j.saa.2006.09.015. Epub 2006 Sep 16. [PubMed:17049912  ] 
  2. Kant Bhatia S, Gurav R, Choi YK, Choi TR, Kim HJ, Song HS, Mi Lee S, Lee Park S, Soo Lee H, Kim YG, Ahn J, Yang YH: Bioprospecting of exopolysaccharide from marine Sphingobium yanoikuyae BBL01: Production, characterization, and metal chelation activity. Bioresour Technol. 2021 Mar;324:124674. doi: 10.1016/j.biortech.2021.124674. Epub 2021 Jan 7. [PubMed:33445012  ] 
  3. Sahin-Toth M, Akhoon KM, Runner J, Kaback HR: Ligand recognition by the lactose permease of Escherichia coli: specificity and affinity are defined by distinct structural elements of galactopyranosides. Biochemistry. 2000 May 2;39(17):5097-103. doi: 10.1021/bi0000263. [PubMed:10819976  ] 
  4. LOTUS database [Link]