NP-MRD: Showing NP-Card for (-)-Upunoside A (NP0072535)

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Record Information

Version

1.0

Created at

2022-04-28 17:52:45 UTC

Updated at

2022-04-28 17:52:45 UTC

NP-MRD ID

NP0072535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Upunoside A

Description

(1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-6-[(1S)-2-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(4-hydroxyphenyl)ethyl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]Nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (-)-Upunoside A is found in Upuna borneensis. It was first documented in 2022 (PMID: 35489815). Based on a literature review a significant number of articles have been published on (1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-6-[(1S)-2-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(4-hydroxyphenyl)ethyl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0⁴,¹⁸.0⁷,¹⁹.0¹¹,¹⁶]Nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol (PMID: 35489814) (PMID: 35489813) (PMID: 35489812) (PMID: 35489811).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219522D          

 96110  0  0  1  0            999 V2000
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M  END

     RDKit          3D

160174  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282219522D          

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M  END
> <DATABASE_ID>
NP0072535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(C[C@@H](C3=CC=C(O)C=C3)C3=C4O[C@@H]([C@@H]5C4=C4[C@@H]([C@H]([C@@H](C4=C3O)C3=CC(O)=CC4=C3[C@@H]([C@@H](O4)C3=CC=C(O)C=C3)C3=CC(O)=CC(O)=C3)C3=CC=C(O)C=C3)[C@@H](C3=CC=C(O)C=C3)C3=C5C=C(O)C=C3O)C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C76H64O20/c77-32-56-69(89)71(91)72(92)76(95-56)93-50-22-33(21-45(83)27-50)23-51(34-1-11-40(78)12-2-34)64-70(90)67-62(53-29-49(87)31-55-61(53)59(39-24-46(84)26-47(85)25-39)73(94-55)37-7-17-43(81)18-8-37)58(36-5-15-42(80)16-6-36)65-57(35-3-13-41(79)14-4-35)60-52(28-48(86)30-54(60)88)63-68(66(65)67)75(64)96-74(63)38-9-19-44(82)20-10-38/h1-22,24-31,51,56-59,62-63,65,69,71-74,76-92H,23,32H2/t51-,56+,57-,58-,59-,62-,63-,65+,69+,71-,72+,73-,74+,76+/m0/s1

> <INCHI_KEY>
WMPBMVQBTNKOKJ-KSCQIDOVSA-N

> <FORMULA>
C76H64O20

> <MOLECULAR_WEIGHT>
1297.328

> <EXACT_MASS>
1296.399094461

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
130.7000820336317

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-6-[(1S)-2-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(4-hydroxyphenyl)ethyl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11(16),12,14,18-hexaene-5,13,15-triol

> <ALOGPS_LOGP>
6.13

> <JCHEM_LOGP>
11.208783422000003

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
15

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.07905300941891

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.683063637681965

> <JCHEM_PKA_STRONGEST_BASIC>
-5.258878649705022

> <JCHEM_POLAR_SURFACE_AREA>
360.6

> <JCHEM_REFRACTIVITY>
350.1789

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,9S,10S,17S)-3-[(2R,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-6-[(1S)-2-(3-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-1-(4-hydroxyphenyl)ethyl]-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.0^{4,18}.0^{7,19}.0^{11,16}]nonadeca-4,6,11(16),12,14,18-hexaene-5,13,15-triol

> <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      -2.929  -3.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.676  -2.519   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.274  -3.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.126  -4.689   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.379  -5.584   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.781  -4.946   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.231  -7.117   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.979  -2.261   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.991  -0.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.145   0.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.188   1.822   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.656   2.286   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.159   1.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.460  -0.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.428  -1.455   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.968  -1.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.920  -0.234   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.567   1.265   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.175   1.924   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.824   3.514   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.294   3.688   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.855   4.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.379   6.123   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.410   7.267   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.916   6.947   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.392   5.482   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.361   4.338   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.947   8.091   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.689   2.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.164   1.876   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.516   0.377   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.395  -0.678   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.748  -2.177   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.285   2.932   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.646  -2.827   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.182  -2.932   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.860  -4.315   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.001  -5.593   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.465  -5.488   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.787  -4.106   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.679  -6.976   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.440  -2.749   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.892  -4.221   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.393  -4.566   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.845  -6.038   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.796  -7.165   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.295  -6.821   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.843  -5.349   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.249  -8.637   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -1.300   3.413   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.616   4.365   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -1.752   5.405   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -3.220   4.941   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.356   5.981   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -4.024   7.485   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -2.555   7.949   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -1.419   6.909   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -2.223   9.452   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -3.359  10.492   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -4.827  10.028   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -5.964  11.068   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -5.631  12.572   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -4.163  13.035   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -3.027  11.996   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -1.558  12.460   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -3.830  14.539   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -6.767  13.611   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      -7.432  10.604   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      -8.568  11.644   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      -5.825   5.517   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      -2.417   2.398   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      -2.749   0.894   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -4.034   0.547   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      -5.354   1.470   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      -5.255   3.341   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      -3.553   3.438   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      -6.726   0.771   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      -1.797  -0.263   0.000  0.00  0.00           O+0
HETATM   79  C   UNK     0      -2.140  -1.050   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      -3.680  -1.038   0.000  0.00  0.00           C+0
HETATM   81  O   UNK     0      -4.168  -2.498   0.000  0.00  0.00           O+0
HETATM   82  C   UNK     0      -4.575   0.216   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      -6.108   0.067   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      -7.003   1.320   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      -6.365   2.722   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      -4.832   2.871   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      -3.937   1.617   0.000  0.00  0.00           C+0
HETATM   88  O   UNK     0      -7.260   3.975   0.000  0.00  0.00           O+0
HETATM   89  C   UNK     0      -1.225   0.188   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      -1.840   1.600   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      -0.924   2.839   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0       0.606   2.665   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0       1.221   1.253   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       0.305   0.015   0.000  0.00  0.00           C+0
HETATM   95  O   UNK     0       2.751   1.080   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0      -1.539   4.251   0.000  0.00  0.00           O+0
CONECT    1    2    6   81                                                  
CONECT    2    1    3   79                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    3    9   42                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   78                                                  
CONECT   11   10   12   50                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   17   35                                                  
CONECT   17   16   18   32                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   12                                                       
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   25                                                            
CONECT   29   18   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   17   33                                                  
CONECT   33   32                                                            
CONECT   34   30                                                            
CONECT   35   16   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   38                                                            
CONECT   42   15    8   43                                                  
CONECT   43   42   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   49                                                  
CONECT   47   46   48                                                       
CONECT   48   47   43                                                       
CONECT   49   46                                                            
CONECT   50   11   51   71                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   70                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56   52                                                       
CONECT   58   56   59                                                       
CONECT   59   58   60   64                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   68                                                  
CONECT   62   61   63   67                                                  
CONECT   63   62   64   66                                                  
CONECT   64   63   59   65                                                  
CONECT   65   64                                                            
CONECT   66   63                                                            
CONECT   67   62                                                            
CONECT   68   61   69                                                       
CONECT   69   68                                                            
CONECT   70   54                                                            
CONECT   71   50   72   76                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75   77                                                  
CONECT   75   74   76                                                       
CONECT   76   75   71                                                       
CONECT   77   74                                                            
CONECT   78   10                                                            
CONECT   79    2   80   89                                                  
CONECT   80   79   81   82                                                  
CONECT   81   80    1                                                       
CONECT   82   80   83   87                                                  
CONECT   83   82   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   86   88                                                  
CONECT   86   85   87                                                       
CONECT   87   86   82                                                       
CONECT   88   85                                                            
CONECT   89   79   90   94                                                  
CONECT   90   89   91                                                       
CONECT   91   90   92   96                                                  
CONECT   92   91   93                                                       
CONECT   93   92   94   95                                                  
CONECT   94   93   89                                                       
CONECT   95   93                                                            
CONECT   96   91                                                            
MASTER        0    0    0    0    0    0    0    0   96    0  220    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇₆H₆₄O₂₀

Average Mass

1297.3280 Da

Monoisotopic Mass

1296.39909 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(C[C@@H](C3=CC=C(O)C=C3)C3=C4O[C@@H]([C@@H]5C4=C4[C@@H]([C@H]([C@@H](C4=C3O)C3=CC(O)=CC4=C3[C@@H]([C@@H](O4)C3=CC=C(O)C=C3)C3=CC(O)=CC(O)=C3)C3=CC=C(O)C=C3)[C@@H](C3=CC=C(O)C=C3)C3=C5C=C(O)C=C3O)C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C76H64O20/c77-32-56-69(89)71(91)72(92)76(95-56)93-50-22-33(21-45(83)27-50)23-51(34-1-11-40(78)12-2-34)64-70(90)67-62(53-29-49(87)31-55-61(53)59(39-24-46(84)26-47(85)25-39)73(94-55)37-7-17-43(81)18-8-37)58(36-5-15-42(80)16-6-36)65-57(35-3-13-41(79)14-4-35)60-52(28-48(86)30-54(60)88)63-68(66(65)67)75(64)96-74(63)38-9-19-44(82)20-10-38/h1-22,24-31,51,56-59,62-63,65,69,71-74,76-92H,23,32H2/t51-,56+,57-,58-,59-,62-,63-,65+,69+,71-,72+,73-,74+,76+/m0/s1

InChI Key

WMPBMVQBTNKOKJ-KSCQIDOVSA-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
Upuna borneensis	Plant	KNApSAcK

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 glycoside
Lignan glycoside
4-prenylated 2-arybenzofuran
Linear 1,7-diphenylheptane skeleton
Neolignan skeleton
1-phenylcoumaran
Phenolic glycoside
Dibenzocycloheptene
Stilbene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Coumaran
Indane
Benzofuran
Phenoxy compound
Resorcinol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	6.13	ALOGPS
logP	11.21	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.68	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	360.6 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	350.18 m³·mol⁻¹	ChemAxon
Polarizability	130.7 Å³	ChemAxon
Number of Rings	15	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

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

162853535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Ye X, Zhang Z, Zhao Q, Xiang Y, Xu N, Wang Q, Pan Y, Guo X, Wang Z: Genetic diversity and selection signatures of four indigenous pig breeds from eastern China. Anim Genet. 2022 Apr 30. doi: 10.1111/age.13208. [PubMed:35489815 ]
Wu A, Fahey MT, Cui D, El-Behesy B, Story DA: An evaluation of the outcome metric 'days alive and at home' in older patients after hip fracture surgery. Anaesthesia. 2022 Apr 30. doi: 10.1111/anae.15742. [PubMed:35489814 ]
Martinez-Pizarro S: Prolotherapy with dextrose to reduce pain in osteoarthritis of the knee. Reumatol Clin (Engl Ed). 2022 Apr;18(4):251-252. doi: 10.1016/j.reumae.2020.08.002. Epub 2021 Apr 5. [PubMed:35489813 ]
Gryspeerdt E, Mutluoglu M, Rummens S, Van Wambeke P, Peers K: Wasting of the hand is not fate! A case of missed true neurogenic thoracic outlet syndrome. Reumatol Clin (Engl Ed). 2022 Apr;18(4):249-250. doi: 10.1016/j.reumae.2021.05.005. [PubMed:35489812 ]
Tezcan ME, Volkan O, Mercan R, Sen N, Yilmaz-Oner S: Familial mediterranean fever patients may have unmet needs for the treatments of exertional leg pain and enthesitis. Reumatol Clin (Engl Ed). 2022 Apr;18(4):227-230. doi: 10.1016/j.reumae.2021.02.009. [PubMed:35489811 ]

Showing NP-Card for (-)-Upunoside A (NP0072535)

MOL for NP0072535 ((-)-Upunoside A)

3D MOL for NP0072535 ((-)-Upunoside A)

3D SDF for NP0072535 ((-)-Upunoside A)

3D-SDF for NP0072535 ((-)-Upunoside A)

PDB for NP0072535 ((-)-Upunoside A)

3D PDB for NP0072535 ((-)-Upunoside A)

SMILES for NP0072535 ((-)-Upunoside A)

INCHI for NP0072535 ((-)-Upunoside A)

Structure for NP0072535 ((-)-Upunoside A)

3D Structure for NP0072535 ((-)-Upunoside A)