NP-MRD: Showing NP-Card for 4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid (NP0156397)

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Record Information

Version

2.0

Created at

2022-09-02 13:36:02 UTC

Updated at

2022-09-02 13:36:02 UTC

NP-MRD ID

NP0156397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid

Description

4-[(6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. 4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid is found in Dianthus caryophyllus. 4-[(6-{[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507212D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251507212D          

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 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 16 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
 13 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC(O)=O)C(=O)OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2)C2=CC=C(O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O14/c26-11-3-1-10(2-4-11)23-17(7-13-14(28)5-12(27)6-16(13)37-23)38-25-22(34)21(33)20(32)18(39-25)9-36-24(35)15(29)8-19(30)31/h1-6,15,18,20-22,25-29,32-34H,7-9H2,(H,30,31)

> <INCHI_KEY>
BUYVRDKTUIDPKL-UHFFFAOYSA-N

> <FORMULA>
C25H26O14

> <MOLECULAR_WEIGHT>
550.469

> <EXACT_MASS>
550.132255517

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.73304076769546

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
-0.7357400813333339

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.709295384164552

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5501397697447445

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491034791118997

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
127.99330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid

> <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      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.672  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      20.005  -3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      24.006  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      25.340  -3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.674  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      28.007  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.341  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      30.675  -3.850   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.008  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.008  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      33.342  -8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      30.675  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.341  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      28.007  -8.470   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      29.341  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.007  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.341  -1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      28.007  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.007   0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.341   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      29.341   3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      30.675   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      30.675  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      26.674  -6.160   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      24.006  -6.160   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      24.006  -7.700   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      21.339  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   38                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25   15                                                       
CONECT   27   16   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   13   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   11   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoate	Generator

Chemical Formula

C₂₅H₂₆O₁₄

Average Mass

550.4690 Da

Monoisotopic Mass

550.13226 Da

IUPAC Name

4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid

Traditional Name

4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

OC(CC(O)=O)C(=O)OCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2)C2=CC=C(O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C25H26O14/c26-11-3-1-10(2-4-11)23-17(7-13-14(28)5-12(27)6-16(13)37-23)38-25-22(34)21(33)20(32)18(39-25)9-36-24(35)15(29)8-19(30)31/h1-6,15,18,20-22,25-29,32-34H,7-9H2,(H,30,31)

InChI Key

BUYVRDKTUIDPKL-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
Dianthus caryophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Isochromane
Benzopyran
2-benzopyran
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Lactone
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Dialkyl ether
Alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxybenzoic acid (CHEBI:81153 )

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	0.7	ALOGPS
logP	-0.74	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.99 m³·mol⁻¹	ChemAxon
Polarizability	51.73 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 4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid (NP0156397)

MOL for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

3D MOL for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

3D SDF for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

3D-SDF for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

PDB for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

3D PDB for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

SMILES for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

INCHI for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

Structure for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)

3D Structure for NP0156397 (4-[(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3-hydroxy-4-oxobutanoic acid)