NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid (NP0221083)

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Record Information

Version

2.0

Created at

2022-09-05 22:34:04 UTC

Updated at

2022-09-05 22:34:05 UTC

NP-MRD ID

NP0221083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

3',4',5-Trihydroxy-3-methoxy-6,7-methylenedioxyflavone 4'-glucuronide belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. 3',4',5-Trihydroxy-3-methoxy-6,7-methylenedioxyflavone 4'-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3',4',5-Trihydroxy-3-methoxy-6,7-methylenedioxyflavone 4'-glucuronide has been detected, but not quantified in, green vegetables and spinachs. 3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid is found in Spinacia oleracea. This could make 3',4',5-trihydroxy-3-methoxy-6,7-methylenedioxyflavone 4'-glucuronide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310002D          

 37 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061310002D          

 37 41  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0221083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC(O)=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O14/c1-32-20-14(26)12-10(5-11-19(13(12)25)34-6-33-11)35-18(20)7-2-3-9(8(24)4-7)36-23-17(29)15(27)16(28)21(37-23)22(30)31/h2-5,15-17,21,23-25,27-29H,6H2,1H3,(H,30,31)

> <INCHI_KEY>
CHIQYVBCRPLTQS-UHFFFAOYSA-N

> <FORMULA>
C23H20O14

> <MOLECULAR_WEIGHT>
520.3965

> <EXACT_MASS>
520.085305348

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
48.845602891761594

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.24813208733333353

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.665029885726991

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9722709847865056

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868279752815907

> <JCHEM_POLAR_SURFACE_AREA>
210.89999999999995

> <JCHEM_REFRACTIVITY>
117.41119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2H-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)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       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.199  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.507  -3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.865   0.237   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       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.866   4.087   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.532   4.857   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.866   2.547   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.199   4.087   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.865   4.857   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.532   1.777   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.865   1.777   0.000  0.00  0.00           O+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      13.200   4.857   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.532   6.397   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       6.531   4.087   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.865   6.397   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.531  -5.153   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.602  -2.367   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.602  -4.859   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.532   0.237   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.199   2.547   0.000  0.00  0.00           O+0
CONECT    1   32                                                            
CONECT    2    3    7                                                       
CONECT    3    2    9                                                       
CONECT    4    7    8                                                       
CONECT    5   10   11                                                       
CONECT    6   33   34                                                       
CONECT    7    2    4   18                                                  
CONECT    8    4    9   24                                                  
CONECT    9    3    8   36                                                  
CONECT   10    5   12   35                                                  
CONECT   11    5   19   33                                                  
CONECT   12   10   13   14                                                  
CONECT   13   12   19   25                                                  
CONECT   14   12   20   26                                                  
CONECT   15   16   17   27                                                  
CONECT   16   15   21   28                                                  
CONECT   17   15   23   29                                                  
CONECT   18    7   20   35                                                  
CONECT   19   11   13   34                                                  
CONECT   20   14   18   32                                                  
CONECT   21   16   22   37                                                  
CONECT   22   21   30   31                                                  
CONECT   23   17   36   37                                                  
CONECT   24    8                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   16                                                            
CONECT   29   17                                                            
CONECT   30   22                                                            
CONECT   31   22                                                            
CONECT   32    1   20                                                       
CONECT   33    6   11                                                       
CONECT   34    6   19                                                       
CONECT   35   10   18                                                       
CONECT   36    9   23                                                       
CONECT   37   21   23                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₃H₂₀O₁₄

Average Mass

520.3965 Da

Monoisotopic Mass

520.08531 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC3=C(OCO3)C(O)=C2C1=O)C1=CC(O)=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1

InChI Identifier

InChI=1S/C23H20O14/c1-32-20-14(26)12-10(5-11-19(13(12)25)34-6-33-11)35-18(20)7-2-3-9(8(24)4-7)36-23-17(29)15(27)16(28)21(37-23)22(30)31/h2-5,15-17,21,23-25,27-29H,6H2,1H3,(H,30,31)

InChI Key

CHIQYVBCRPLTQS-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 vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Polyol
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.22	ALOGPS
logP	0.25	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	210.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.41 m³·mol⁻¹	ChemAxon
Polarizability	48.85 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	No	ChemAxon

External Links

HMDB ID

HMDB0037757

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016897

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

74978486

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-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid (NP0221083)

MOL for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

3D MOL for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

3D SDF for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

3D-SDF for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

PDB for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

3D PDB for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

SMILES for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

INCHI for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

Structure for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)

3D Structure for NP0221083 (3,4,5-trihydroxy-6-(2-hydroxy-4-{9-hydroxy-7-methoxy-8-oxo-2h-[1,3]dioxolo[4,5-g]chromen-6-yl}phenoxy)oxane-2-carboxylic acid)