NP-MRD: Showing NP-Card for (2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate (NP0324002)

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Record Information

Version

2.0

Created at

2022-09-12 03:47:57 UTC

Updated at

2022-09-12 03:47:57 UTC

NP-MRD ID

NP0324002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate

Description

(2-{[3-(Benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. (2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate is found in Itoa orientalis. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251506192D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251506192D          

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 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=C(O)C=C2COC(=O)C2=CC=CC=C2O)C(OC(=O)C2=CC=CC=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O11/c28-13-21-22(31)23(32)24(38-25(33)15-6-2-1-3-7-15)27(37-21)36-20-11-10-17(29)12-16(20)14-35-26(34)18-8-4-5-9-19(18)30/h1-12,21-24,27-32H,13-14H2

> <INCHI_KEY>
UTRVZPDCXSMOPG-UHFFFAOYSA-N

> <FORMULA>
C27H26O11

> <MOLECULAR_WEIGHT>
526.494

> <EXACT_MASS>
526.147511657

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.38856455016092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
3.6677316876666666

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.996454538829184

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.393931507579465

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810929926360634

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
130.60500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
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   24                                                  
CONECT   24   23                                                            
CONECT   25    5   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   25   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₆O₁₁

Average Mass

526.4940 Da

Monoisotopic Mass

526.14751 Da

IUPAC Name

(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate

Traditional Name

(2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC=C(O)C=C2COC(=O)C2=CC=CC=C2O)C(OC(=O)C2=CC=CC=C2)C(O)C1O

InChI Identifier

InChI=1S/C27H26O11/c28-13-21-22(31)23(32)24(38-25(33)15-6-2-1-3-7-15)27(37-21)36-20-11-10-17(29)12-16(20)14-35-26(34)18-8-4-5-9-19(18)30/h1-12,21-24,27-32H,13-14H2

InChI Key

UTRVZPDCXSMOPG-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
Itoa orientalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-hydroxybenzoic acid ester
O-glycosyl compound
Benzoate ester
Salicylic acid or derivatives
Benzyloxycarbonyl
4-alkoxyphenol
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Primary alcohol
Organic oxide
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	2.08	ALOGPS
logP	3.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.6 m³·mol⁻¹	ChemAxon
Polarizability	51.39 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

75049608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate (NP0324002)

MOL for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

3D MOL for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

3D SDF for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

3D-SDF for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

PDB for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

3D PDB for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

SMILES for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

INCHI for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

Structure for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)

3D Structure for NP0324002 ((2-{[3-(benzoyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxyphenyl)methyl 2-hydroxybenzoate)