NP-MRD: Showing NP-Card for (3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan (NP0062685)

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Record Information

Version

2.0

Created at

2022-04-28 07:16:23 UTC

Updated at

2022-04-28 07:16:23 UTC

NP-MRD ID

NP0062685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan

Description

Kanzonol I belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. (3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan is found in Glycyrrhiza uralensis . Based on a literature review very few articles have been published on Kanzonol I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209162D          

 32 35  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    4.5375    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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   -2.8874   -1.0513   -0.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1503   -2.4150   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3948   -2.9079    0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4620   -2.0596    0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7081   -2.6057    0.6122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2088   -0.7068    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.2193   -0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7564    1.1464   -0.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331    2.1055    0.1756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2383    2.9970    1.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861    2.9506   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2081   -1.0921   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535   -0.5429    2.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6342    0.2770    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2803    1.7405    3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9762    0.7148    3.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3145   -3.0723   -0.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6294    2.4088    2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 37  1  0
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 31 63  1  0
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  4 36  1  0
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M  END


  Mrv1652304282209162D          

 32 35  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -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>
NP0062685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C(OC)=C2C[C@@H](COC2=C1)C1=CC=C(O)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O5/c1-16(2)7-8-20-23(29-5)14-24-21(25(20)30-6)13-17(15-31-24)18-9-10-22(28)19-11-12-27(3,4)32-26(18)19/h7,9-12,14,17,28H,8,13,15H2,1-6H3/t17-/m0/s1

> <INCHI_KEY>
RVKDAOFCDAPVGX-KRWDZBQOSA-N

> <FORMULA>
C27H32O5

> <MOLECULAR_WEIGHT>
436.548

> <EXACT_MASS>
436.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.11417756219087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethyl-2H-chromen-5-ol

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.809091068999999

> <ALOGPS_LOGS>
-5.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.627282467140652

> <JCHEM_PKA_STRONGEST_BASIC>
-4.269906901712567

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
128.54190000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.817   0.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.540  -0.716   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334   8.470   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
CONECT    1    2    6   31                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21   22                                             
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18                                                            
CONECT   22   18                                                            
CONECT   23   14                                                            
CONECT   24    3   25                                                       
CONECT   25   24                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    1   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₅

Average Mass

436.5480 Da

Monoisotopic Mass

436.22497 Da

IUPAC Name

8-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethyl-2H-chromen-5-ol

Traditional Name

8-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2,2-dimethylchromen-5-ol

CAS Registry Number

Not Available

SMILES

COC1=C(CC=C(C)C)C(OC)=C2C[C@@H](COC2=C1)C1=CC=C(O)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C27H32O5/c1-16(2)7-8-20-23(29-5)14-24-21(25(20)30-6)13-17(15-31-24)18-9-10-22(28)19-11-12-27(3,4)32-26(18)19/h7,9-12,14,17,28H,8,13,15H2,1-6H3/t17-/m0/s1

InChI Key

RVKDAOFCDAPVGX-KRWDZBQOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
5-methoxyisoflavonoid-skeleton
7-methoxyisoflavonoid-skeleton
Isoflavanol
Isoflavan
2,2-dimethyl-1-benzopyran
1-benzopyran
Chromane
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	5.45	ALOGPS
logP	5.81	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.54 m³·mol⁻¹	ChemAxon
Polarizability	49.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019335

Chemspider ID

103885513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101667240

PDB ID

Not Available

ChEBI ID

175520

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan (NP0062685)

MOL for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

3D MOL for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

3D SDF for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

3D-SDF for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

PDB for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

3D PDB for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

SMILES for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

INCHI for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

Structure for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)

3D Structure for NP0062685 ((3R)-4'-Hydroxy-5,7-dimethoxy-6-prenyl-6'',6''-dimethylpyrano[2'',3'':2',3']isoflavan)