NP-MRD: Showing NP-Card for Roburin E (NP0333054)

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Record Information

Version

1.0

Created at

2024-05-04 04:28:02 UTC

Updated at

2024-05-06 00:10:57 UTC

NP-MRD ID

NP0333054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roburin E

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162307042D          

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 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 30 38  1  0  0  0  0
 26 39  1  0  0  0  0
 21 40  2  0  0  0  0
 19 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  2  0  0  0  0
 52 60  1  0  0  0  0
 48 61  1  0  0  0  0
 43 62  2  0  0  0  0
 41 63  1  0  0  0  0
 63 64  1  6  0  0  0
 64 65  1  0  0  0  0
 38 65  1  0  0  0  0
 65 66  2  0  0  0  0
 63 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 60 69  1  0  0  0  0
 69 70  2  0  0  0  0
  3 71  1  0  0  0  0
 17 71  1  0  0  0  0
 71 72  2  0  0  0  0
 23 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 73 75  2  0  0  0  0
  2 75  1  0  0  0  0
 75 76  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CO[C@@](O)([C@@H](O)[C@@H]1O)[C@@H]1[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(O)C(O)=C(O)C=C1C(=O)O[C@@H]1COC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)O[C@H]1[C@@H]2OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C46H34O30/c47-9-1-6-14(28(55)24(9)51)15-7(2-10(48)25(52)29(15)56)43(67)74-37-13(5-71-41(6)65)73-42(66)8-3-11(49)26(53)30(57)16(8)17-20-18(32(59)35(62)31(17)58)19-21-22(34(61)36(63)33(19)60)23(38(75-45(21)69)39(37)76-44(20)68)46(70)40(64)27(54)12(50)4-72-46/h1-3,12-13,23,27,37-40,47-64,70H,4-5H2/t12?,13-,23+,27-,37-,38?,39+,40+,46-/m1/s1

> <INCHI_KEY>
ZVFDKYBWZMATCT-HDKMNXNASA-N

> <FORMULA>
C46H34O30

> <MOLECULAR_WEIGHT>
1066.748

> <EXACT_MASS>
1066.113489695

> <JCHEM_ACCEPTOR_COUNT>
25

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
92.55080333129843

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
19

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,20R,42S,46S)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-46-[(2R,3S,4R)-2,3,4,5-tetrahydroxyoxan-2-yl]-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1^{38,42}.0^{2,20}.0^{5,10}.0^{11,16}.0^{23,28}.0^{33,45}.0^{34,39}]hexatetraconta-5,7,9,11,13,15,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <JCHEM_LOGP>
0.4706321163333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.396472073034993

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.849672417206177

> <JCHEM_PKA_STRONGEST_BASIC>
-6.176121906972993

> <JCHEM_POLAR_SURFACE_AREA>
525.1000000000001

> <JCHEM_REFRACTIVITY>
239.38090000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,20R,42S,46S)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-46-[(2R,3S,4R)-2,3,4,5-tetrahydroxyoxan-2-yl]-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1^{38,42}.0^{2,20}.0^{5,10}.0^{11,16}.0^{23,28}.0^{33,45}.0^{34,39}]hexatetraconta-5,7,9,11,13,15,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-JAN-23         0                                  
HETATM    1  O   UNK     0       0.593  -9.860   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.067  -8.468   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.829  -7.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.422  -6.981   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.318  -8.233   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.396  -7.133   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.929  -8.898   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.659  -8.028   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.810 -10.434   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.421 -11.098   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.081 -11.304   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.962 -12.840   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.470 -10.639   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.589  -9.104   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.131  -5.519   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.132  -4.388   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.622  -4.503   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.257  -3.239   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.888  -4.014   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.793  -2.819   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.170  -2.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.488  -2.726   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.721  -3.842   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.150  -3.127   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.390  -4.040   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.405  -1.586   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.177  -0.648   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.431   0.871   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.698  -1.140   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.462  -0.018   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.523   1.165   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.047   1.386   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.009   2.610   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.976   3.794   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.527   2.872   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.059   4.317   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.512   1.689   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.980   0.244   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.837  -1.018   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.214  -1.170   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.260  -3.170   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.909  -4.567   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       7.209  -5.392   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.749  -5.382   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.832  -6.920   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.205  -7.618   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      10.287  -9.155   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      11.495  -6.777   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.413  -5.239   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      12.703  -4.399   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      10.040  -4.542   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.671  -3.137   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.104  -3.701   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      13.470  -4.412   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      13.309  -2.742   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      14.742  -3.306   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      13.080  -1.219   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      14.285  -0.260   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      11.647  -0.655   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.443  -1.614   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      12.868  -7.475   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0       6.784  -6.872   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       5.470  -1.644   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       5.045  -0.099   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       3.548   0.315   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       3.721   1.845   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       6.472  -0.474   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       7.947  -0.032   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0       9.427  -0.457   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      10.252   0.844   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      -0.002  -5.858   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      -1.548  -5.570   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -2.346  -6.956   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      -3.886  -6.926   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      -1.618  -8.344   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      -2.467  -9.629   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   75                                                  
CONECT    3    2    4   71                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    5                                                       
CONECT   15    4   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   71                                                  
CONECT   18   17                                                            
CONECT   19   15   20   41                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   40                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   72                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   39                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22   30                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   30   65                                                  
CONECT   39   26                                                            
CONECT   40   21                                                            
CONECT   41   19   42   63                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   62                                                  
CONECT   44   43   45   51                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   61                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51   53   60                                                  
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   52   69                                                  
CONECT   61   48                                                            
CONECT   62   43                                                            
CONECT   63   41   64   67                                                  
CONECT   64   63   65                                                       
CONECT   65   64   38   66                                                  
CONECT   66   65                                                            
CONECT   67   63   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   60   70                                                  
CONECT   70   69                                                            
CONECT   71    3   17   72                                                  
CONECT   72   71   23   73                                                  
CONECT   73   72   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73    2   76                                                  
CONECT   76   75                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  170    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₃₄O₃₀

Average Mass

1066.7480 Da

Monoisotopic Mass

1066.11349 Da

IUPAC Name

(1R,2R,20R,42S,46S)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-46-[(2R,3S,4R)-2,3,4,5-tetrahydroxyoxan-2-yl]-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1^{38,42}.0^{2,20}.0^{5,10}.0^{11,16}.0^{23,28}.0^{33,45}.0^{34,39}]hexatetraconta-5,7,9,11,13,15,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1CO[C@@](O)([C@@H](O)[C@@H]1O)[C@@H]1[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(O)C(O)=C(O)C=C1C(=O)O[C@@H]1COC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)O[C@H]1[C@@H]2OC3=O

InChI Identifier

InChI=1S/C46H34O30/c47-9-1-6-14(28(55)24(9)51)15-7(2-10(48)25(52)29(15)56)43(67)74-37-13(5-71-41(6)65)73-42(66)8-3-11(49)26(53)30(57)16(8)17-20-18(32(59)35(62)31(17)58)19-21-22(34(61)36(63)33(19)60)23(38(75-45(21)69)39(37)76-44(20)68)46(70)40(64)27(54)12(50)4-72-46/h1-3,12-13,23,27,37-40,47-64,70H,4-5H2/t12?,13-,23+,27-,37-,38?,39+,40+,46-/m1/s1

InChI Key

ZVFDKYBWZMATCT-HDKMNXNASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.27, CD₃OD, simulated)	benjamin.metoyer@gmail.com	Institut des sciences de la vigne et du vin	Métoyer	2024-05-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
sativa		Not Available

Chemical Taxonomy

Classification

Not classified

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	0.47	ChemAxon
pKa (Strongest Acidic)	6.85	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	525.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	239.38 m³·mol⁻¹	ChemAxon
Polarizability	92.55 Å³	ChemAxon
Number of Rings	10	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

Not Available

References

General References

Metoyer B, Renouf E, Jourdes M, Merillon JM, Teguo PW: Isolation of Hydrolyzable Tannins from Castanea sativa Using Centrifugal Partition Chromatography. J Nat Prod. 2024 Apr 26;87(4):652-663. doi: 10.1021/acs.jnatprod.3c00524. Epub 2024 Feb 15. [PubMed:38359463 ]

Showing NP-Card for Roburin E (NP0333054)

MOL for NP0333054 (Roburin E)

3D MOL for NP0333054 (Roburin E)

3D SDF for NP0333054 (Roburin E)

3D-SDF for NP0333054 (Roburin E)

PDB for NP0333054 (Roburin E)

3D PDB for NP0333054 (Roburin E)

SMILES for NP0333054 (Roburin E)

INCHI for NP0333054 (Roburin E)

Structure for NP0333054 (Roburin E)

3D Structure for NP0333054 (Roburin E)