NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid (NP0185159)

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Record Information

Version

2.0

Created at

2022-09-04 00:29:22 UTC

Updated at

2022-09-04 00:29:22 UTC

NP-MRD ID

NP0185159

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

Description

2-(3,4-Dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid is found in Lithospermum erythrorhizon. 2-(3,4-Dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511342D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241511342D          

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 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  7 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 18 16  1  4  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
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 20 32  1  0  0  0  0
 25 32  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 33 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(CC1=CC=C(O)C(O)=C1)OC(=O)C=CC1=CC=C(O)C2=C1C(C(O2)C1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O12/c1-38-28(37)21(11-13-2-6-16(29)19(32)10-13)39-22(34)9-5-14-3-8-18(31)26-23(14)24(27(35)36)25(40-26)15-4-7-17(30)20(33)12-15/h2-10,12,21,24-25,29-33H,11H2,1H3,(H,35,36)

> <INCHI_KEY>
YQEVPWOGQQZUKO-UHFFFAOYSA-N

> <FORMULA>
C28H24O12

> <MOLECULAR_WEIGHT>
552.488

> <EXACT_MASS>
552.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.19406309149608

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.8915644166666663

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.883884106247717

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3287678472614695

> <JCHEM_PKA_STRONGEST_BASIC>
-4.961634309300382

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
137.84159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   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  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.682 -13.826   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.150 -13.987   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.524 -12.580   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.018 -12.260   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.542 -10.796   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.987 -13.405   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.380 -15.321   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.150 -16.655   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.380 -17.988   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.840 -17.988   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.070 -19.322   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.070 -16.655   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.530 -16.655   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.840 -15.321   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7                                                       
CONECT   15    5   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   20   25                                                  
CONECT   33   27   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylate	Generator

Chemical Formula

C₂₈H₂₄O₁₂

Average Mass

552.4880 Da

Monoisotopic Mass

552.12678 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

Traditional Name

2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C(CC1=CC=C(O)C(O)=C1)OC(=O)C=CC1=CC=C(O)C2=C1C(C(O2)C1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C28H24O12/c1-38-28(37)21(11-13-2-6-16(29)19(32)10-13)39-22(34)9-5-14-3-8-18(31)26-23(14)24(27(35)36)25(40-26)15-4-7-17(30)20(33)12-15/h2-10,12,21,24-25,29-33H,11H2,1H3,(H,35,36)

InChI Key

YQEVPWOGQQZUKO-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
Lithospermum erythrorhizon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Coumaran
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ether
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
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	3.53	ALOGPS
logP	3.89	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	137.84 m³·mol⁻¹	ChemAxon
Polarizability	53.19 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid (NP0185159)

MOL for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D MOL for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D SDF for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D-SDF for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

PDB for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D PDB for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

SMILES for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

INCHI for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

Structure for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)

3D Structure for NP0185159 (2-(3,4-dihydroxyphenyl)-4-(3-{[3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]oxy}-3-oxoprop-1-en-1-yl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid)