NP-MRD: Showing NP-Card for [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate (NP0309846)

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Record Information

Version

2.0

Created at

2022-09-11 04:43:10 UTC

Updated at

2022-09-11 04:43:10 UTC

NP-MRD ID

NP0309846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

[5-({4,5-Dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-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. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate is found in Cucurbita moschata. [5-({4,5-Dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171514372D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171514372D          

 39 42  0  0  0  0            999 V2000
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   -0.9784   -2.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5269   -5.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0118   -6.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 29 35  1  0  0  0  0
 23 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 38  1  0  0  0  0
 38 39  2  0  0  0  0
  4 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1=CC=C(OC2OC(CO)C(O)C(O)C2OC2OCC(O)(COC(=O)C3=CC=C(O)C=C3)C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O13/c27-10-9-14-1-7-17(8-2-14)37-24-21(20(31)19(30)18(11-28)38-24)39-25-22(32)26(34,13-36-25)12-35-23(33)15-3-5-16(29)6-4-15/h1-8,18-22,24-25,27-32,34H,9-13H2

> <INCHI_KEY>
AYLSGEWHCBDIDG-UHFFFAOYSA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.63305692117747

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-0.16184069433333276

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.793177814958815

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.497251267798148

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4044066135785087

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
130.22729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.62e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       6.471 -15.192   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.566 -13.946   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.034 -14.107   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.129 -12.861   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.597 -13.022   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.692 -11.776   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.319 -10.369   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.413  -9.123   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.118  -9.284   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.745 -10.691   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.276 -10.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.902 -12.259   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.434 -12.420   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.181  -9.606   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.713  -9.767   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.555  -8.199   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.460  -6.954   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.023  -8.038   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.397  -6.632   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.302  -5.386   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.842  -5.386   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.318  -3.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.072  -3.016   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.103  -1.871   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.042  -1.871   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.535  -2.192   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.495  -1.047   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.001  -1.367   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.019   0.417   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.487   0.738   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.963   2.202   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.933   3.347   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.408   4.811   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.574   3.027   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.050   1.562   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.826  -3.921   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.362  -3.445   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.850 -10.208   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.755 -11.454   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   38                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   36                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   29                                                       
CONECT   36   23   20   37                                                  
CONECT   37   36                                                            
CONECT   38    7   39                                                       
CONECT   39   38    4                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₆H₃₂O₁₃

Average Mass

552.5290 Da

Monoisotopic Mass

552.18429 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCCC1=CC=C(OC2OC(CO)C(O)C(O)C2OC2OCC(O)(COC(=O)C3=CC=C(O)C=C3)C2O)C=C1

InChI Identifier

InChI=1S/C26H32O13/c27-10-9-14-1-7-17(8-2-14)37-24-21(20(31)19(30)18(11-28)38-24)39-25-22(32)26(34,13-36-25)12-35-23(33)15-3-5-16(29)6-4-15/h1-8,18-22,24-25,27-32,34H,9-13H2

InChI Key

AYLSGEWHCBDIDG-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
Cucurbita moschata	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
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Disaccharide
O-glycosyl compound
Benzoate ester
Tyrosol derivative
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Oxolane
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Primary alcohol
Hydrocarbon derivative
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	0.16	ALOGPS
logP	-0.16	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.23 m³·mol⁻¹	ChemAxon
Polarizability	55.63 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

72963809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate (NP0309846)

MOL for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

3D MOL for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

3D SDF for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

3D-SDF for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

PDB for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

3D PDB for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

SMILES for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

INCHI for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

Structure for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)

3D Structure for NP0309846 ([5-({4,5-dihydroxy-2-[4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxan-3-yl}oxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate)