NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0249831)

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Record Information

Version

2.0

Created at

2022-09-07 12:30:21 UTC

Updated at

2022-09-07 12:30:21 UTC

NP-MRD ID

NP0249831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Beta-D-Glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamate) belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. (2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Balanophora japonica. Based on a literature review very few articles have been published on beta-D-Glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamate).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214302D          

 36 38  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -6.6000    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
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 O   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
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    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072214302D          

 36 38  0  0  1  0            999 V2000
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4315    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0249831

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H24O12/c25-11-18-21(32)23(35-19(30)7-3-12-1-5-14(26)16(28)9-12)22(33)24(34-18)36-20(31)8-4-13-2-6-15(27)17(29)10-13/h1-10,18,21-29,32-33H,11H2/b7-3+,8-4+/t18-,21-,22-,23+,24+/m1/s1

> <INCHI_KEY>
KIODQZXMNGIVNL-DRXQJDLMSA-N

> <FORMULA>
C24H24O12

> <MOLECULAR_WEIGHT>
504.444

> <EXACT_MASS>
504.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.33462872513378

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.9209809313333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.50860132167162

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.907288489582744

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9811133023626466

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
122.9824

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.005   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      21.339   4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   35                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   21   14   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
b-D-Glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamate)	Generator
b-D-Glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamic acid)	Generator
beta-D-Glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamic acid)	Generator
Β-D-glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamate)	Generator
Β-D-glucopyranose 1,3-bis(3,4-dihydroxy-trans-cinnamic acid)	Generator

Chemical Formula

C₂₄H₂₄O₁₂

Average Mass

504.4440 Da

Monoisotopic Mass

504.12678 Da

IUPAC Name

(2S,3R,4S,5R,6R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5R,6R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C24H24O12/c25-11-18-21(32)23(35-19(30)7-3-12-1-5-14(26)16(28)9-12)22(33)24(34-18)36-20(31)8-4-13-2-6-15(27)17(29)10-13/h1-10,18,21-29,32-33H,11H2/b7-3+,8-4+/t18-,21-,22-,23+,24+/m1/s1

InChI Key

KIODQZXMNGIVNL-DRXQJDLMSA-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
Balanophora japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Organic oxygen compound
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	1.92	ChemAxon
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.98 m³·mol⁻¹	ChemAxon
Polarizability	48.33 Å³	ChemAxon
Number of Rings	3	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

9937568

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11762872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0249831)

MOL for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0249831 ((2s,3r,4s,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)