NP-MRD: Showing NP-Card for 2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate (NP0154553)

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Record Information

Version

2.0

Created at

2022-09-02 11:29:07 UTC

Updated at

2022-09-02 11:29:07 UTC

NP-MRD ID

NP0154553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate

Description

2-{[5-(Benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate 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. 2-{[5-(Benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181501282D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004181501282D          

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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 28 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(CO)(OC2OC(CO)C(OC(=O)C3=CC=CC=C3)C(O)C2O)C(OC(=O)C2=CC=CC=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O13/c27-11-16-18(30)22(37-24(34)15-9-5-2-6-10-15)26(13-29,38-16)39-25-20(32)19(31)21(17(12-28)35-25)36-23(33)14-7-3-1-4-8-14/h1-10,16-22,25,27-32H,11-13H2

> <INCHI_KEY>
BGZXEUWUJYFRMD-UHFFFAOYSA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.513

> <EXACT_MASS>
550.168641026

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.75658022367896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[3-(benzoyloxy)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl benzoate

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
0.4617647336666663

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.86743436961049

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.158454174131595

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981453257794252

> <JCHEM_POLAR_SURFACE_AREA>
201.66999999999996

> <JCHEM_REFRACTIVITY>
128.41810000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[3-(benzoyloxy)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       3.716  -9.643   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.343  -8.236   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.913  -5.525   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.637  -3.476   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.113  -2.011   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.698  -3.476   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.204  -3.796   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.235  -2.651   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.741  -2.971   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.771  -1.827   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.278  -2.147   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.217  -4.436   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.723  -4.756   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.199  -6.221   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.169  -7.365   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.705  -6.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.736  -5.397   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.242  -5.717   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.718  -7.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.688  -8.326   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.181  -8.006   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.186  -5.581   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.662  -7.045   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.680  -5.260   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.650  -6.405   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.043  -5.049   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.188  -6.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.867  -7.586   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.652  -5.604   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.797  -6.634   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.261  -6.158   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.581  -4.652   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.437  -3.622   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.972  -4.098   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.992  -8.236   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   28                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   14   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    9   27                                                  
CONECT   27   26                                                            
CONECT   28    5   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   28    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoic acid	Generator

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5130 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

6-{[3-(benzoyloxy)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl benzoate

Traditional Name

6-{[3-(benzoyloxy)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(CO)(OC2OC(CO)C(OC(=O)C3=CC=CC=C3)C(O)C2O)C(OC(=O)C2=CC=CC=C2)C1O

InChI Identifier

InChI=1S/C26H30O13/c27-11-16-18(30)22(37-24(34)15-9-5-2-6-10-15)26(13-29,38-16)39-25-20(32)19(31)21(17(12-28)35-25)36-23(33)14-7-3-1-4-8-14/h1-10,16-22,25,27-32H,11-13H2

InChI Key

BGZXEUWUJYFRMD-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

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

C-glycosyl compound
Disaccharide
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Ketal
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxide
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-0.09	ALOGPS
logP	0.46	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	12.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	128.42 m³·mol⁻¹	ChemAxon
Polarizability	52.76 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate (NP0154553)

MOL for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

3D MOL for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

3D SDF for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

3D-SDF for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

PDB for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

3D PDB for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

SMILES for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

INCHI for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

Structure for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)

3D Structure for NP0154553 (2-{[5-(benzoyloxy)-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl benzoate)