NP-MRD: Showing NP-Card for 3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid (NP0289200)

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Record Information

Version

2.0

Created at

2022-09-09 19:16:20 UTC

Updated at

2022-09-09 19:16:20 UTC

NP-MRD ID

NP0289200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid

Description

3-{3-[4-(2-Carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid is found in Spiraea formosana. 3-{3-[4-(2-Carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231517272D          

 35 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004231517272D          

 35 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0289200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC=C(C=CC(O)=O)C=C2OC2=CC=C(CCC(O)=O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O11/c25-12-18-21(30)22(31)23(32)24(35-18)34-16-8-3-14(5-10-20(28)29)11-17(16)33-15-6-1-13(2-7-15)4-9-19(26)27/h1-3,5-8,10-11,18,21-25,30-32H,4,9,12H2,(H,26,27)(H,28,29)

> <INCHI_KEY>
ZFEVXDHEJZHVDH-UHFFFAOYSA-N

> <FORMULA>
C24H26O11

> <MOLECULAR_WEIGHT>
490.461

> <EXACT_MASS>
490.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.65175994357145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
1.1470569823333336

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.922680828769078

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3110761107556197

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549142165

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
119.33460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17                                                       
CONECT   17   16    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29                                                       
CONECT   29   28   19                                                       
CONECT   30    5   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoate	Generator

Chemical Formula

C₂₄H₂₆O₁₁

Average Mass

490.4610 Da

Monoisotopic Mass

490.14751 Da

IUPAC Name

3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid

Traditional Name

3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(OC2=CC=C(C=CC(O)=O)C=C2OC2=CC=C(CCC(O)=O)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C24H26O11/c25-12-18-21(30)22(31)23(32)24(35-18)34-16-8-3-14(5-10-20(28)29)11-17(16)33-15-6-1-13(2-7-15)4-9-19(26)27/h1-3,5-8,10-11,18,21-25,30-32H,4,9,12H2,(H,26,27)(H,28,29)

InChI Key

ZFEVXDHEJZHVDH-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
Spiraea formosana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Diphenylether
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Diaryl ether
O-glycosyl compound
3-phenylpropanoic-acid
Styrene
Phenoxy compound
Phenol ether
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	0.68	ALOGPS
logP	1.15	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	119.33 m³·mol⁻¹	ChemAxon
Polarizability	48.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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 3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid (NP0289200)

MOL for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

3D MOL for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

3D SDF for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

3D-SDF for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

PDB for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

3D PDB for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

SMILES for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

INCHI for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

Structure for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)

3D Structure for NP0289200 (3-{3-[4-(2-carboxyethyl)phenoxy]-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl}prop-2-enoic acid)