NP-MRD: Showing NP-Card for (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate (NP0303498)

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Record Information

Version

2.0

Created at

2022-09-10 17:53:13 UTC

Updated at

2022-09-10 17:53:14 UTC

NP-MRD ID

NP0303498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(5-{[4,5-Dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate belongs to the class of organic compounds known as o-glycosyl compounds. (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate is found in Catalpa bignonioides. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]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


  Mrv1533004171500072D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171500072D          

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    4.6971   -5.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -6.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260   -6.8190    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 21 34  1  0  0  0  0
 18 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OCCC2=CC=C(O)C=C2)C(OC2OCC(O)(COC(=O)C3=CC=C(O)C=C3)C2O)C(O)C1O

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

> <INCHI_KEY>
MWVDTRFZEALNIG-UHFFFAOYSA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.92776289506409

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.33539175333333393

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.199740659231203

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.48876864033737

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836372259617

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
130.49620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]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       5.357 -14.297   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.452 -13.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.078 -11.644   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.173 -10.398   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.800  -8.991   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.894  -7.745   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.363  -7.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.458  -6.660   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.074  -6.821   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.700  -8.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.232  -8.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.137  -7.143   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.669  -7.304   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.511  -5.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.979  -5.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.331  -8.830   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.958  -7.423   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.052  -6.177   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.512  -6.177   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.037  -4.713   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.282  -3.808   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.252  -2.663   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.313  -2.663   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.819  -2.983   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.850  -1.839   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.374  -0.374   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.356  -2.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.386  -1.015   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.893  -1.335   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.369  -2.799   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.875  -3.120   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.338  -3.944   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.832  -3.624   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.528  -4.713   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.993  -4.237   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.236 -10.076   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.768  -9.915   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.610 -11.483   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.515 -12.729   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   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
CONECT   16    5   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   34                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   34                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27                                                       
CONECT   34   21   18   35                                                  
CONECT   35   34                                                            
CONECT   36   16   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    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
(5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]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-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(OCCC2=CC=C(O)C=C2)C(OC2OCC(O)(COC(=O)C3=CC=C(O)C=C3)C2O)C(O)C1O

InChI Identifier

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

InChI Key

MWVDTRFZEALNIG-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
Catalpa bignonioides	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

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Disaccharide
O-glycosyl compound
Benzoate ester
Tyrosol derivative
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Oxane
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
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	0.21	ALOGPS
logP	0.34	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-3	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	130.5 m³·mol⁻¹	ChemAxon
Polarizability	54.93 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 (5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate (NP0303498)

MOL for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

3D MOL for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

3D SDF for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

3D-SDF for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

PDB for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

3D PDB for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

SMILES for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

INCHI for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

Structure for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)

3D Structure for NP0303498 ((5-{[4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-hydroxyphenyl)ethoxy]oxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate)