NP-MRD: Showing NP-Card for [(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate (NP0215481)

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Record Information

Version

2.0

Created at

2022-09-05 15:07:06 UTC

Updated at

2022-09-05 15:07:06 UTC

NP-MRD ID

NP0215481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate

Description

Maritimetin 6-o-(3'',4'',6''-tri-o-acetylglucoside) belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton. Thus, maritimetin 6-O-(3'',4'',6''-tri-O-acetylglucoside) is considered to be a flavonoid. [(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate is found in Bidens pilosa. Based on a literature review very few articles have been published on Maritimetin 6-o-(3'',4'',6''-tri-o-acetylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309052217072D          

 41 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652309052217072D          

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    8.3536    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 20 27  1  0  0  0  0
 18 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  2  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0215481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](OC2=CC=C3C(=O)\C(OC3=C2O)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O14/c1-11(28)36-10-20-25(37-12(2)29)26(38-13(3)30)23(35)27(41-20)40-18-7-5-15-21(33)19(39-24(15)22(18)34)9-14-4-6-16(31)17(32)8-14/h4-9,20,23,25-27,31-32,34-35H,10H2,1-3H3/b19-9-/t20-,23-,25-,26-,27-/m1/s1

> <INCHI_KEY>
AHLQXSOCSBYAFH-LVNWGQRMSA-N

> <FORMULA>
C27H26O14

> <MOLECULAR_WEIGHT>
574.491

> <EXACT_MASS>
574.132255517

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.61544030678158

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{[(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate

> <JCHEM_LOGP>
1.0433211673333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.937724898119539

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.173876165901357

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9696325060713393

> <JCHEM_POLAR_SURFACE_AREA>
204.57999999999998

> <JCHEM_REFRACTIVITY>
134.5688

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4R,5R,6S)-3,4-bis(acetyloxy)-6-{[(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.926  -3.317   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592  -2.547   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.259  -3.317   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.592  -1.007   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259   1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.925   2.073   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.630   6.844   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.400   8.178   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.090   6.844   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.320   8.178   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.320   5.510   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.926   4.383   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.260   6.693   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.926   1.303   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.593   1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20                                                       
CONECT   28   18   13   29                                                  
CONECT   29   28                                                            
CONECT   30    8   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32    6   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆O₁₄

Average Mass

574.4910 Da

Monoisotopic Mass

574.13226 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](OC2=CC=C3C(=O)\C(OC3=C2O)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H26O14/c1-11(28)36-10-20-25(37-12(2)29)26(38-13(3)30)23(35)27(41-20)40-18-7-5-15-21(33)19(39-24(15)22(18)34)9-14-4-6-16(31)17(32)8-14/h4-9,20,23,25-27,31-32,34-35H,10H2,1-3H3/b19-9-/t20-,23-,25-,26-,27-/m1/s1

InChI Key

AHLQXSOCSBYAFH-LVNWGQRMSA-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
Bidens pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Aurone O-glycosides

Alternative Parents

Substituents

Aurone-6-o-glycoside
Aurone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Benzofuran
Tricarboxylic acid or derivatives
Coumaran
Aryl ketone
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Secondary alcohol
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014667

Chemspider ID

8778584

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10603216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate (NP0215481)

MOL for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

PDB for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

SMILES for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

INCHI for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

Structure for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0215481 ([(2r,3r,4r,5r,6s)-3,4-bis(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-5-hydroxyoxan-2-yl]methyl acetate)