NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate (NP0163913)

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Record Information

Version

2.0

Created at

2022-09-02 22:41:02 UTC

Updated at

2022-09-02 22:41:02 UTC

NP-MRD ID

NP0163913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Maritimetin 6-o-(3'',6''-di-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'',6''-di-O-acetylglucoside) is considered to be a flavonoid. [(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate is found in Bidens bipinnata. Based on a literature review very few articles have been published on Maritimetin 6-o-(3'',6''-di-o-acetylglucoside).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309032200412D          

 38 41  0  0  1  0            999 V2000
    6.9246   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4957    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6 37  1  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652309032200412D          

 38 41  0  0  1  0            999 V2000
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 32 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0163913

> <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]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O13/c1-10(26)34-9-18-21(32)24(35-11(2)27)22(33)25(38-18)37-16-6-4-13-19(30)17(36-23(13)20(16)31)8-12-3-5-14(28)15(29)7-12/h3-8,18,21-22,24-25,28-29,31-33H,9H2,1-2H3/b17-8-/t18-,21-,22-,24+,25-/m1/s1

> <INCHI_KEY>
SYQJGLLUDJCHQW-ZZEXXIAZSA-N

> <FORMULA>
C25H24O13

> <MOLECULAR_WEIGHT>
532.454

> <EXACT_MASS>
532.121690833

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.16544084909584

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
0.6021957570000003

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.937695871046538

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.173870150397192

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6638877694415255

> <JCHEM_POLAR_SURFACE_AREA>
198.51

> <JCHEM_REFRACTIVITY>
125.4173

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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
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                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₃

Average Mass

532.4540 Da

Monoisotopic Mass

532.12169 Da

IUPAC Name

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

Traditional Name

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

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]1O

InChI Identifier

InChI=1S/C25H24O13/c1-10(26)34-9-18-21(32)24(35-11(2)27)22(33)25(38-18)37-16-6-4-13-19(30)17(36-23(13)20(16)31)8-12-3-5-14(28)15(29)7-12/h3-8,18,21-22,24-25,28-29,31-33H,9H2,1-2H3/b17-8-/t18-,21-,22-,24+,25-/m1/s1

InChI Key

SYQJGLLUDJCHQW-ZZEXXIAZSA-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 bipinnata	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
Coumaran
Benzofuran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Ketone
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.3	ALOGPS
logP	0.6	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	125.42 m³·mol⁻¹	ChemAxon
Polarizability	52.17 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

C00014666

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

101273170

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,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate (NP0163913)

MOL for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

3D MOL for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

3D SDF for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

3D-SDF for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

PDB for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

3D PDB for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

SMILES for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

INCHI for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

Structure for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)

3D Structure for NP0163913 ([(2r,3r,4s,5r,6s)-4-(acetyloxy)-6-{[(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3-oxo-1-benzofuran-6-yl]oxy}-3,5-dihydroxyoxan-2-yl]methyl acetate)