NP-MRD: Showing NP-Card for 6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol (NP0294543)

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Record Information

Version

2.0

Created at

2022-09-10 03:08:32 UTC

Updated at

2022-09-10 03:08:32 UTC

NP-MRD ID

NP0294543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

6-({[2-({[3,4-Dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol 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. 6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol is found in Claviceps purpurea. Based on a literature review very few articles have been published on 6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205082D          

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M  END

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  Mrv1652309102205082D          

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M  END
> <DATABASE_ID>
NP0294543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(CO)(OCC2(OCC3OC(O)C(O)C(O)C3O)OC(CO)C(O)C2O)C(O)C1O

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

> <INCHI_KEY>
CRNLZFIITYEFDG-UHFFFAOYSA-N

> <FORMULA>
C18H32O16

> <MOLECULAR_WEIGHT>
504.438

> <EXACT_MASS>
504.16903495

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.366661639937874

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-6.125130709333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.84158812203338

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.181136349732423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486668176794463

> <JCHEM_POLAR_SURFACE_AREA>
268.67999999999995

> <JCHEM_REFRACTIVITY>
101.62480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       3.796  -8.283   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.170  -6.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.075  -5.630   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.599  -4.166   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.845  -3.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.814  -2.116   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.308  -2.436   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.875  -2.116   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.382  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.412  -1.292   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.443  -2.436   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.967  -3.901   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.997  -5.045   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.504  -4.725   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.534  -5.869   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.040  -5.549   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.058  -7.334   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.089  -8.479   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.552  -7.654   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.076  -9.119   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.521  -6.510   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.015  -6.830   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.166  -0.387   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.642   1.078   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.737   2.324   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.205   2.163   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.182   1.078   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.087   2.324   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.658  -0.387   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.123  -0.862   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.091  -4.166   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.555  -3.690   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.615  -5.630   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.520  -6.876   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   31                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   10   30                                                  
CONECT   30   29                                                            
CONECT   31    5   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₂O₁₆

Average Mass

504.4380 Da

Monoisotopic Mass

504.16903 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(CO)(OCC2(OCC3OC(O)C(O)C(O)C3O)OC(CO)C(O)C2O)C(O)C1O

InChI Identifier

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

InChI Key

CRNLZFIITYEFDG-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
Claviceps purpurea	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
Ketal
Oxane
Tetrahydrofuran
Hemiacetal
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-6.1	ChemAxon
pKa (Strongest Acidic)	11.18	ChemAxon
pKa (Strongest Basic)	-3.6	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	46.37 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162867654

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol (NP0294543)

MOL for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

3D MOL for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

3D SDF for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

3D-SDF for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

PDB for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

3D PDB for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

SMILES for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

INCHI for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

Structure for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)

3D Structure for NP0294543 (6-({[2-({[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol)