NP-MRD: Showing NP-Card for 5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol (NP0325253)

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Record Information

Version

1.0

Created at

2022-09-12 05:51:40 UTC

Updated at

2022-09-12 05:51:40 UTC

NP-MRD ID

NP0325253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

Description

Prunus inhibitor b, also known as PIb, belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Prunus inhibitor b is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, prunus inhibitor b has been detected, but not quantified in, fruits. 5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol is found in Prunus jacquemontii, Prunus persica, Prunus prostrata and Prunus spinosa. This could make prunus inhibitor b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309572D          

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M  END

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  Mrv0541 05061309572D          

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    3.6457   -4.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -0.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9805   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574   -0.9117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -2.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  1  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 13  2  2  0  0  0  0
 13  3  1  0  0  0  0
 14  4  2  0  0  0  0
 14  5  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17  6  1  0  0  0  0
 18 11  2  0  0  0  0
 18 16  1  0  0  0  0
 19  7  1  0  0  0  0
 19 17  2  0  0  0  0
 20  8  1  0  0  0  0
 21 10  1  0  0  0  0
 22  9  2  0  0  0  0
 23 11  1  0  0  0  0
 24 20  2  0  0  0  0
 24 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 12  1  0  0  0  0
 27 21  1  0  0  0  0
 28 16  2  0  0  0  0
 28 25  1  0  0  0  0
 29 26  1  0  0  0  0
 30 13  1  0  0  0  0
 30 29  1  0  0  0  0
 31 14  1  0  0  0  0
 32 15  1  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 38 29  1  0  0  0  0
 39 27  1  0  0  0  0
 39 28  1  0  0  0  0
 40 22  1  0  0  0  0
 40 30  1  0  0  0  0
 41 23  1  0  0  0  0
 41 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C1=C(OC3(OC4=CC(O)=CC(O)=C4C1C3O)C1=CC=C(O)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O11/c31-14-4-2-13(3-5-14)30-29(38)26(24-20(36)8-15(32)9-22(24)40-30)25-23(41-30)11-18(34)16-10-21(37)27(39-28(16)25)12-1-6-17(33)19(35)7-12/h1-9,11,21,26-27,29,31-38H,10H2

> <INCHI_KEY>
MXKKFADFYXJREN-UHFFFAOYSA-N

> <FORMULA>
C30H24O11

> <MOLECULAR_WEIGHT>
560.505

> <EXACT_MASS>
560.13186161

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
55.646164634066295

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
3.8940974183333332

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.187769053046475

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.748166891541448

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2931729512486436

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
142.21540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.145  -6.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.903  -3.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.379  -5.636   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.167  -4.327   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.642  -6.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.649  -5.993   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.572  -3.718   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.319   2.144   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.228  -0.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.633  -7.315   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.051  -5.372   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.106  -5.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.509  -4.101   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.036  -5.862   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.497   1.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.594  -6.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.114  -4.525   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.090  -6.509   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.076  -3.387   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.129   1.619   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.136  -6.985   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.219  -0.889   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.517  -3.904   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.398   0.102   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.021  -3.573   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.953  -1.727   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.602  -5.517   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.060  -4.710   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.218  -3.087   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.018  -3.406   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.300  -6.742   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.089   1.665   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.618  -4.194   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.457  -8.035   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.541  -1.919   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.160   3.263   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.805  -8.500   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.472  -1.702   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       5.564  -4.380   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.414  -1.702   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -0.134  -4.965   0.000  0.00  0.00           O+0
CONECT    1    6   12                                                       
CONECT    2    4   13                                                       
CONECT    3    5   13                                                       
CONECT    4    2   14                                                       
CONECT    5    3   14                                                       
CONECT    6    1   17                                                       
CONECT    7   12   19                                                       
CONECT    8   15   20                                                       
CONECT    9   15   22                                                       
CONECT   10   16   21                                                       
CONECT   11   18   23                                                       
CONECT   12    1    7   27                                                  
CONECT   13    2    3   30                                                  
CONECT   14    4    5   31                                                  
CONECT   15    8    9   32                                                  
CONECT   16   10   18   28                                                  
CONECT   17    6   19   33                                                  
CONECT   18   11   16   34                                                  
CONECT   19    7   17   35                                                  
CONECT   20    8   24   36                                                  
CONECT   21   10   27   37                                                  
CONECT   22    9   24   40                                                  
CONECT   23   11   25   41                                                  
CONECT   24   20   22   26                                                  
CONECT   25   23   26   28                                                  
CONECT   26   24   25   29                                                  
CONECT   27   12   21   39                                                  
CONECT   28   16   25   39                                                  
CONECT   29   26   30   38                                                  
CONECT   30   13   29   40   41                                             
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   29                                                            
CONECT   39   27   28                                                       
CONECT   40   22   30                                                       
CONECT   41   23   30                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,3',4',5,7-pentahydroxyflavan	HMDB
ent-Epiafzelechin(2a->7,4a->8)catechin	HMDB
PIb	HMDB

Chemical Formula

C₃₀H₂₄O₁₁

Average Mass

560.5050 Da

Monoisotopic Mass

560.13186 Da

IUPAC Name

5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

Traditional Name

5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol

CAS Registry Number

Not Available

SMILES

OC1CC2=C(OC1C1=CC(O)=C(O)C=C1)C1=C(OC3(OC4=CC(O)=CC(O)=C4C1C3O)C1=CC=C(O)C=C1)C=C2O

InChI Identifier

InChI=1S/C30H24O11/c31-14-4-2-13(3-5-14)30-29(38)26(24-20(36)8-15(32)9-22(24)40-30)25-23(41-30)11-18(34)16-10-21(37)27(39-28(16)25)12-1-6-17(33)19(35)7-12/h1-9,11,21,26-27,29,31-38H,10H2

InChI Key

MXKKFADFYXJREN-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
Prunus jacquemontii	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Prunus prostrata	LOTUS Database	35616633
Prunus spinosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Not Available

Substituents

Not Available

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	2.61	ALOGPS
logP	3.89	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	142.22 m³·mol⁻¹	ChemAxon
Polarizability	55.65 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016814

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

14586216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol (NP0325253)

MOL for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

3D MOL for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

3D SDF for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

3D-SDF for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

PDB for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

3D PDB for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

SMILES for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

INCHI for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

Structure for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)

3D Structure for NP0325253 (5-(3,4-dihydroxyphenyl)-13-(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol)