NP-MRD: Showing NP-Card for (2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid (NP0268712)

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Record Information

Version

2.0

Created at

2022-09-08 13:55:23 UTC

Updated at

2022-09-08 13:55:24 UTC

NP-MRD ID

NP0268712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid

Description

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid is found in Salvia miltiorrhiza. Based on a literature review very few articles have been published on (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082215552D          

 40 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082215552D          

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 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
  6 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  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>
NP0268712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@@H](OC2=C(O)C=CC(\C=C\C(=O)O[C@H](CC3=CC=C(O)C(O)=C3)C(O)=O)=C12)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O12/c1-38-28(37)24-23-14(3-8-18(31)26(23)40-25(24)15-4-7-17(30)20(33)12-15)5-9-22(34)39-21(27(35)36)11-13-2-6-16(29)19(32)10-13/h2-10,12,21,24-25,29-33H,11H2,1H3,(H,35,36)/b9-5+/t21-,24-,25+/m1/s1

> <INCHI_KEY>
NFOCYHUCMXEHDG-JATIPLDZSA-N

> <FORMULA>
C28H24O12

> <MOLECULAR_WEIGHT>
552.488

> <EXACT_MASS>
552.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.310857292357646

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid

> <JCHEM_LOGP>
3.8915644166666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.879978831332958

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.088542715837162

> <JCHEM_PKA_STRONGEST_BASIC>
-4.967440275536227

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
137.8416

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.143   1.728   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.680   2.552   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   4.087   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924   4.857   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.591   4.857   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925   7.167   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925   8.707   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591   9.477   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591  11.017   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925  11.787   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.925  13.327   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.259  11.017   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.592  11.787   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.259   9.477   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258   7.167   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.924   6.397   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.258   8.707   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.090  -2.637   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.630  -2.637   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.940  -1.303   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.400   1.365   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.090   0.031   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   32                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   13   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    7   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    6   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31    5   33                                                  
CONECT   33   32   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
(2R)-3-(3,4-Dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoate	Generator

Chemical Formula

C₂₈H₂₄O₁₂

Average Mass

552.4880 Da

Monoisotopic Mass

552.12678 Da

IUPAC Name

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid

Traditional Name

(2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-[(2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1[C@@H](OC2=C(O)C=CC(\C=C\C(=O)O[C@H](CC3=CC=C(O)C(O)=C3)C(O)=O)=C12)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C28H24O12/c1-38-28(37)24-23-14(3-8-18(31)26(23)40-25(24)15-4-7-17(30)20(33)12-15)5-9-22(34)39-21(27(35)36)11-13-2-6-16(29)19(32)10-13/h2-10,12,21,24-25,29-33H,11H2,1H3,(H,35,36)/b9-5+/t21-,24-,25+/m1/s1

InChI Key

NFOCYHUCMXEHDG-JATIPLDZSA-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
Salvia miltiorrhiza	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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
3-phenylpropanoic-acid
Tricarboxylic acid or derivatives
Coumaran
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	3.89	ChemAxon
pKa (Strongest Acidic)	3.09	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	53.31 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

98789388

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid (NP0268712)

MOL for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

3D MOL for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

3D SDF for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

3D-SDF for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

PDB for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

3D PDB for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

SMILES for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

INCHI for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

Structure for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)

3D Structure for NP0268712 ((2r)-3-(3,4-dihydroxyphenyl)-2-{[(2e)-3-[(2r,3r)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3-(methoxycarbonyl)-2,3-dihydro-1-benzofuran-4-yl]prop-2-enoyl]oxy}propanoic acid)