NP-MRD: Showing NP-Card for (6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0178213)

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Record Information

Version

2.0

Created at

2022-09-03 16:09:58 UTC

Updated at

2022-09-03 16:09:58 UTC

NP-MRD ID

NP0178213

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Description

Kaempferol 7-(6''-galloylglucoside) belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Kaempferol 7-(6''-galloylglucoside) is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309472D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061309472D          

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   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  3  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  2  0  0  0  0
 17  8  2  0  0  0  0
 18  9  1  0  0  0  0
 19 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 10  1  0  0  0  0
 26 24  2  0  0  0  0
 27 11  1  0  0  0  0
 28 25  1  0  0  0  0
 29 12  1  0  0  0  0
 30 14  1  0  0  0  0
 31 15  1  0  0  0  0
 32 16  1  0  0  0  0
 33 20  1  0  0  0  0
 34 21  1  0  0  0  0
 35 22  2  0  0  0  0
 36 23  1  0  0  0  0
 37 24  1  0  0  0  0
 38 25  1  0  0  0  0
 39 27  2  0  0  0  0
 40  9  1  0  0  0  0
 40 27  1  0  0  0  0
 41 13  1  0  0  0  0
 41 28  1  0  0  0  0
 42 17  1  0  0  0  0
 42 26  1  0  0  0  0
 43 18  1  0  0  0  0
 43 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178213

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O15/c29-12-3-1-10(2-4-12)26-24(37)22(35)19-14(30)7-13(8-17(19)42-26)41-28-25(38)23(36)21(34)18(43-28)9-40-27(39)11-5-15(31)20(33)16(32)6-11/h1-8,18,21,23,25,28-34,36-38H,9H2

> <INCHI_KEY>
PJGFYRIIZPHDJQ-UHFFFAOYSA-N

> <FORMULA>
C28H24O15

> <MOLECULAR_WEIGHT>
600.4812

> <EXACT_MASS>
600.111520098

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
56.21427306523518

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.7764005759999997

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.269108342113904

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.752715501815293

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678965823844716

> <JCHEM_POLAR_SURFACE_AREA>
253.12999999999994

> <JCHEM_REFRACTIVITY>
142.7904

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -12.003   6.930   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    3   10                                                       
CONECT    2    4   10                                                       
CONECT    3    1   12                                                       
CONECT    4    2   12                                                       
CONECT    5   11   15                                                       
CONECT    6   11   16                                                       
CONECT    7   13   14                                                       
CONECT    8   13   17                                                       
CONECT    9   18   40                                                       
CONECT   10    1    2   26                                                  
CONECT   11    5    6   27                                                  
CONECT   12    3    4   29                                                  
CONECT   13    7    8   41                                                  
CONECT   14    7   19   30                                                  
CONECT   15    5   20   31                                                  
CONECT   16    6   20   32                                                  
CONECT   17    8   19   42                                                  
CONECT   18    9   21   43                                                  
CONECT   19   14   17   22                                                  
CONECT   20   15   16   33                                                  
CONECT   21   18   23   34                                                  
CONECT   22   19   24   35                                                  
CONECT   23   21   25   36                                                  
CONECT   24   22   26   37                                                  
CONECT   25   23   28   38                                                  
CONECT   26   10   24   42                                                  
CONECT   27   11   39   40                                                  
CONECT   28   25   41   43                                                  
CONECT   29   12                                                            
CONECT   30   14                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
CONECT   37   24                                                            
CONECT   38   25                                                            
CONECT   39   27                                                            
CONECT   40    9   27                                                       
CONECT   41   13   28                                                       
CONECT   42   17   26                                                       
CONECT   43   18   28                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₄O₁₅

Average Mass

600.4812 Da

Monoisotopic Mass

600.11152 Da

IUPAC Name

(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Traditional Name

(6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1C(O)C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=C3C(OC(=C(O)C3=O)C3=CC=C(O)C=C3)=C2)C1O

InChI Identifier

InChI=1S/C28H24O15/c29-12-3-1-10(2-4-12)26-24(37)22(35)19-14(30)7-13(8-17(19)42-26)41-28-25(38)23(36)21(34)18(43-28)9-40-27(39)11-5-15(31)20(33)16(32)6-11/h1-8,18,21,23,25,28-34,36-38H,9H2

InChI Key

PJGFYRIIZPHDJQ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
Galloyl ester
Gallic acid or derivatives
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
Glycosyl compound
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Chromone
1-benzopyran
Benzoate ester
Benzopyran
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.16	ALOGPS
logP	1.78	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	253.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.79 m³·mol⁻¹	ChemAxon
Polarizability	56.21 Å³	ChemAxon
Number of Rings	5	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

HMDB0037439

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016497

KNApSAcK ID

C00005872

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

74978085

PDB ID

Not Available

ChEBI ID

136617

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0178213)

MOL for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

PDB for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

Structure for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0178213 ((6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)