NP-MRD: Showing NP-Card for (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate (NP0267524)

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Record Information

Version

2.0

Created at

2022-09-08 12:19:51 UTC

Updated at

2022-09-08 12:19:51 UTC

NP-MRD ID

NP0267524

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate

Description

(5-{[2-(Benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate belongs to the class of organic compounds known as o-glycosyl compounds. (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate is found in Viscum articulatum. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517472D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241517472D          

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 33 34  1  0  0  0  0
 16 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267524

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCC2=CC=CC=C2)C(O)C(OC2OCC(O)(COC(=O)C3=CC=CC=C3)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O11/c26-11-17-18(27)20(19(28)23(35-17)32-12-15-7-3-1-4-8-15)36-24-21(29)25(31,14-34-24)13-33-22(30)16-9-5-2-6-10-16/h1-10,17-21,23-24,26-29,31H,11-14H2

> <INCHI_KEY>
JIJCXJQRKVPZKK-UHFFFAOYSA-N

> <FORMULA>
C25H30O11

> <MOLECULAR_WEIGHT>
506.504

> <EXACT_MASS>
506.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.00285149272436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.6538611916666663

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.350097919028155

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.711011701732247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810907776490874

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
121.77940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       0.692 -11.776   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.839 -11.937   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.745 -10.691   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.276 -10.852   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.181  -9.606   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.713  -9.767   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.339 -11.174   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.871 -11.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.497 -12.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.029 -12.903   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.934 -11.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.308 -10.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -8.776 -10.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.555  -8.199   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.460  -6.954   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.023  -8.038   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.397  -6.632   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.302  -5.386   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.842  -5.386   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.318  -3.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.072  -3.016   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.103  -1.871   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.042  -1.871   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.535  -2.192   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.495  -1.047   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.001  -1.367   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.019   0.417   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.487   0.738   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.963   2.202   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.933   3.347   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.574   3.027   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.050   1.562   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.826  -3.921   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.362  -3.445   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.118  -9.284   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.413  -9.123   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   33                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
CONECT   33   21   18   34                                                  
CONECT   34   33                                                            
CONECT   35   16    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoic acid	Generator

Chemical Formula

C₂₅H₃₀O₁₁

Average Mass

506.5040 Da

Monoisotopic Mass

506.17881 Da

IUPAC Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate

Traditional Name

(5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OCC2=CC=CC=C2)C(O)C(OC2OCC(O)(COC(=O)C3=CC=CC=C3)C2O)C1O

InChI Identifier

InChI=1S/C25H30O11/c26-11-17-18(27)20(19(28)23(35-17)32-12-15-7-3-1-4-8-15)36-24-21(29)25(31,14-34-24)13-33-22(30)16-9-5-2-6-10-16/h1-10,17-21,23-24,26-29,31H,11-14H2

InChI Key

JIJCXJQRKVPZKK-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
Viscum articulatum	LOTUS Database	35616633

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

Disaccharide
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Benzenoid
Oxane
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxide
Hydrocarbon derivative
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	0.36	ALOGPS
logP	0.65	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.71	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	121.78 m³·mol⁻¹	ChemAxon
Polarizability	52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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 (5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate (NP0267524)

MOL for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

3D MOL for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

3D SDF for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

3D-SDF for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

PDB for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

3D PDB for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

SMILES for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

INCHI for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

Structure for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)

3D Structure for NP0267524 ((5-{[2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl benzoate)