NP-MRD: Showing NP-Card for Yuccaol B (NP0331443)

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Record Information

Version

1.0

Created at

2023-01-14 16:09:47 UTC

Updated at

2024-04-19 09:41:21 UTC

NP-MRD ID

NP0331443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yuccaol B

Description

(2'S,3S)-4',6,6'-Trihydroxy-2'-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3,3'-spirobi[2,3-dihydrobenzofuran]-2-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. It was first documented in 2023 (PMID: 37078450). Based on a literature review a significant number of articles have been published on (2'S,3S)-4',6,6'-Trihydroxy-2'-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3,3'-spirobi[2,3-dihydrobenzofuran]-2-one (PMID: 37078444) (PMID: 37078443) (PMID: 37078154) (PMID: 37078114).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652301142317092D          

 37 42  0  0  1  0            999 V2000
    2.2182    5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287    4.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919    4.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    3.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600    2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595    2.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -0.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5270    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2806    1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3669    2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205    2.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880    2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417    2.5617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7017    1.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9481    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -1.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577    0.6220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -0.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6547    0.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    3.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    4.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  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  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 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
 23 30  1  0  0  0  0
 12 31  2  0  0  0  0
 10 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
  8 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  2  0  0  0  0
  2 37  1  0  0  0  0
M  END


  Mrv1652301142317092D          

 37 42  0  0  1  0            999 V2000
    2.2182    5.6495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3287    4.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919    4.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    3.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    3.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6600    2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595    2.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -0.8070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5270    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2806    1.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3669    2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205    2.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7880    2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5417    2.5617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7017    1.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9481    1.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2417   -1.3595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9577    0.6220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4793   -0.8494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6547    0.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4813    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    3.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6758    4.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  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  2  0  0  0  0
 15 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 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
 23 30  1  0  0  0  0
 12 31  2  0  0  0  0
 10 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
  8 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  2  0  0  0  0
  2 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C2=C3C(OC(=O)[C@@]33[C@@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C=C3)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H20O8/c30-18-7-2-15(3-8-18)1-4-17-11-20(32)13-23-25(17)29(28(35)37-23)26-22(34)12-21(33)14-24(26)36-27(29)16-5-9-19(31)10-6-16/h1-14,27,30-34H/b4-1+/t27-,29-/m0/s1

> <INCHI_KEY>
YOJXOIWMUVWNAB-WZUJMHPGSA-N

> <FORMULA>
C29H20O8

> <MOLECULAR_WEIGHT>
496.471

> <EXACT_MASS>
496.115817604

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0       4.141  10.546   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.347   9.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.772   8.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.978   6.909   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.759   5.967   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.965   4.441   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.644   3.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.834   2.177   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.928   0.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.555  -0.476   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.410  -1.506   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.077  -0.736   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.397   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.717   2.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.124   2.903   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.285   4.434   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.692   5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.938   4.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.344   4.782   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.777   2.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.370   1.998   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.383   3.046   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.239   2.016   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.865   0.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.960  -0.637   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.318  -2.538   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.428  -0.476   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.198   0.931   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.788   1.161   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.707   2.177   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.761  -1.586   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.086  -0.637   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.991   0.609   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.555   0.059   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.365   2.016   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.334   6.552   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.128   8.078   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12    9   14   24                                             
CONECT   14   13   15   22                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   13   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   23                                                       
CONECT   31   12                                                            
CONECT   32   10   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    8                                                       
CONECT   36    5   37                                                       
CONECT   37   36    2                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₀O₈

Average Mass

496.4710 Da

Monoisotopic Mass

496.11582 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C2=C3C(OC(=O)[C@@]33[C@@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C=C3)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C29H20O8/c30-18-7-2-15(3-8-18)1-4-17-11-20(32)13-23-25(17)29(28(35)37-23)26-22(34)12-21(33)14-24(26)36-27(29)16-5-9-19(31)10-6-16/h1-14,27,30-34H/b4-1+/t27-,29-/m0/s1

InChI Key

YOJXOIWMUVWNAB-WZUJMHPGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, D2O, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.79 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500.2 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Stilbene
Coumaran
Benzofuran
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Organic oxide
Hydrocarbon derivative
Carbonyl group
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

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

101092684

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Russi AE, Shivakumar P, Luo Z, Bezerra J: Plasticity between ILC2 subsets and amphiregulin expression regulate epithelial repair in biliary atresia. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000418. [PubMed:37078450 ]
Hlady RA, Robertson KD: Epigenetic memory of environmental exposures as a mediator of liver disease. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000414. [PubMed:37078444 ]
Ufere NN: Home is where the liver is?: moving beyond readmissions to time at home as a patient-centered and pragmatic quality measure in cirrhosis care. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000415. [PubMed:37078443 ]
Arnon R, Rubinov A: [[PTOSIS AS A SIGN OF A SYSTEMIC DISEASE]]. Harefuah. 2023 Feb;162(2):119-121. [PubMed:37078154 ]
Shemesh N, Olshaker H: [[A MULTICENTER SPANISH STUDY OF ATROPINE 0.01% IN CHILDHOOD MYOPIA PROGRESSION]]. Harefuah. 2023 Feb;162(2):116-118. [PubMed:37078114 ]

Showing NP-Card for Yuccaol B (NP0331443)

MOL for NP0331443 (Yuccaol B)

3D MOL for NP0331443 (Yuccaol B)

3D SDF for NP0331443 (Yuccaol B)

3D-SDF for NP0331443 (Yuccaol B)

PDB for NP0331443 (Yuccaol B)

3D PDB for NP0331443 (Yuccaol B)

SMILES for NP0331443 (Yuccaol B)

INCHI for NP0331443 (Yuccaol B)

Structure for NP0331443 (Yuccaol B)

3D Structure for NP0331443 (Yuccaol B)