NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid (NP0326447)

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Record Information

Version

2.0

Created at

2022-09-12 08:00:15 UTC

Updated at

2022-09-12 08:00:16 UTC

NP-MRD ID

NP0326447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid

Description

4',5-Dihydroxy-3,3'-dimethoxy-6,7-methylenedioxyflavone 4'-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. 4',5-Dihydroxy-3,3'-dimethoxy-6,7-methylenedioxyflavone 4'-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4',5-Dihydroxy-3,3'-dimethoxy-6,7-methylenedioxyflavone 4'-glucuronide has been detected, but not quantified in, green vegetables and spinachs. 3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid is found in Spinacia oleracea. This could make 4',5-dihydroxy-3,3'-dimethoxy-6,7-methylenedioxyflavone 4'-glucuronide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310002D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061310002D          

 38 42  0  0  0  0            999 V2000
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 37  9  1  0  0  0  0
 37 24  1  0  0  0  0
 38 22  1  0  0  0  0
 38 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C3=C(OCO3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c1-32-10-5-8(3-4-9(10)37-24-18(29)16(27)17(28)22(38-24)23(30)31)19-21(33-2)15(26)13-11(36-19)6-12-20(14(13)25)35-7-34-12/h3-6,16-18,22,24-25,27-29H,7H2,1-2H3,(H,30,31)

> <INCHI_KEY>
SYRSHYBWNZNHHW-UHFFFAOYSA-N

> <FORMULA>
C24H22O14

> <MOLECULAR_WEIGHT>
534.4231

> <EXACT_MASS>
534.100955412

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
50.89101751891252

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2H,8H-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.39402614333333386

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.772708479703432

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0578588196492555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686827976063914

> <JCHEM_POLAR_SURFACE_AREA>
199.89999999999992

> <JCHEM_REFRACTIVITY>
121.89349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2H-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid

> <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       9.199   2.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.199  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.533  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.533  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.200   0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.200  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.200  -4.383   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.866  -0.533   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.197  -6.693   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      15.867   0.237   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      15.867  -2.843   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.200   1.777   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      11.866  -5.153   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.533  -5.153   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.865   1.777   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.602  -2.367   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.532   0.237   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      11.866  -2.073   0.000  0.00  0.00           O+0
CONECT    1   32                                                            
CONECT    2   33                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    8   10                                                       
CONECT    6   11   12                                                       
CONECT    7   34   35                                                       
CONECT    8    3    5   19                                                  
CONECT    9    4   10   37                                                  
CONECT   10    5    9   32                                                  
CONECT   11    6   13   36                                                  
CONECT   12    6   20   34                                                  
CONECT   13   11   14   15                                                  
CONECT   14   13   20   25                                                  
CONECT   15   13   21   26                                                  
CONECT   16   17   18   27                                                  
CONECT   17   16   22   28                                                  
CONECT   18   16   24   29                                                  
CONECT   19    8   21   36                                                  
CONECT   20   12   14   35                                                  
CONECT   21   15   19   33                                                  
CONECT   22   17   23   38                                                  
CONECT   23   22   30   31                                                  
CONECT   24   18   37   38                                                  
CONECT   25   14                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   23                                                            
CONECT   31   23                                                            
CONECT   32    1   10                                                       
CONECT   33    2   21                                                       
CONECT   34    7   12                                                       
CONECT   35    7   20                                                       
CONECT   36   11   19                                                       
CONECT   37    9   24                                                       
CONECT   38   22   24                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2H,8H-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylate	Generator

Chemical Formula

C₂₄H₂₂O₁₄

Average Mass

534.4231 Da

Monoisotopic Mass

534.10096 Da

IUPAC Name

3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2H,8H-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2H-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C3=C(OCO3)C=C2O1

InChI Identifier

InChI=1S/C24H22O14/c1-32-10-5-8(3-4-9(10)37-24-18(29)16(27)17(28)22(38-24)23(30)31)19-21(33-2)15(26)13-11(36-19)6-12-20(14(13)25)35-7-34-12/h3-6,16-18,22,24-25,27-29H,7H2,1-2H3,(H,30,31)

InChI Key

SYRSHYBWNZNHHW-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
Spinacia oleracea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Substituents

Flavonoid-4p-o-glucuronide
3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
Hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
1-o-glucuronide
O-glucuronide
3-methoxychromone
Glucuronic acid or derivatives
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
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	0.99	ALOGPS
logP	0.39	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	199.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	121.89 m³·mol⁻¹	ChemAxon
Polarizability	50.89 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

HMDB0037758

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016898

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

73829990

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid (NP0326447)

MOL for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

3D MOL for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

3D SDF for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

3D-SDF for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

PDB for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

3D PDB for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

SMILES for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

INCHI for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

Structure for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)

3D Structure for NP0326447 (3,4,5-trihydroxy-6-(4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}-2-methoxyphenoxy)oxane-2-carboxylic acid)