NP-MRD: Showing NP-Card for 1,1'; 2,2'-diHHDP-di-glucose (NP0333066)

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Record Information

Version

2.0

Created at

2024-05-04 05:33:52 UTC

Updated at

2024-09-03 04:21:06 UTC

NP-MRD ID

NP0333066

Natural Product DOI

https://doi.org/10.57994/2365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1'; 2,2'-diHHDP-di-glucose

Description

1,1'; 2,2'-DiHHDP-di-glucose belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 1,1'; 2,2'-diHHDP-di-glucose was first documented in 2024 (PMID: 38359463). Based on a literature review very few articles have been published on 1,1'; 2,2'-diHHDP-di-glucose.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162308102D          

 68 74  0  0  1  0            999 V2000
    0.9785   -1.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996   -1.3452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6363   -0.8986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0412    0.0138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3737    0.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 01162308102D          

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M  END
> <DATABASE_ID>
NP0333066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1O[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)C3OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]2C(O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H36O28/c41-5-15-25(51)31(57)33-39(63-15)67-37(61)9-3-13(45)23(49)29(55)19(9)20-10(4-14(46)24(50)30(20)56)38(62)68-40-34(32(58)26(52)16(6-42)64-40)66-36(60)8-2-12(44)22(48)28(54)18(8)17-7(35(59)65-33)1-11(43)21(47)27(17)53/h1-4,15-16,25-26,31-34,39-58H,5-6H2/t15-,16?,25+,26-,31+,32?,33?,34-,39+,40-/m1/s1

> <INCHI_KEY>
HXCLCVSZIRHLDL-BRRUUAGESA-N

> <FORMULA>
C40H36O28

> <MOLECULAR_WEIGHT>
964.7

> <EXACT_MASS>
964.139310519

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
83.55998237919103

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
18

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S,12R,13R,14S,32R,34S,37R)-3,4,5,13,14,20,21,22,25,26,27,33,34,42,43,44-hexadecahydroxy-12,35-bis(hydroxymethyl)-9,11,16,31,36,38-hexaoxaheptacyclo[38.4.0.0^{2,7}.0^{10,15}.0^{18,23}.0^{24,29}.0^{32,37}]tetratetraconta-1(40),2(7),3,5,18(23),19,21,24(29),25,27,41,43-dodecaene-8,17,30,39-tetrone

> <JCHEM_LOGP>
-0.17870380933333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.596778575310155

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.13539072246074

> <JCHEM_PKA_STRONGEST_BASIC>
-5.673424034480512

> <JCHEM_POLAR_SURFACE_AREA>
487.8000000000001

> <JCHEM_REFRACTIVITY>
213.06200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10S,12R,13R,14S,32R,34S,37R)-3,4,5,13,14,20,21,22,25,26,27,33,34,42,43,44-hexadecahydroxy-12,35-bis(hydroxymethyl)-9,11,16,31,36,38-hexaoxaheptacyclo[38.4.0.0^{2,7}.0^{10,15}.0^{18,23}.0^{24,29}.0^{32,37}]tetratetraconta-1(40),2(7),3,5,18(23),19,21,24(29),25,27,41,43-dodecaene-8,17,30,39-tetrone

> <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       1.826  -3.642   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.986  -2.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.666  -1.005   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.188  -1.677   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.810   0.026   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.564   0.931   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.659   2.177   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.315   1.261   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.275  -0.450   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.815  -0.450   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.279   0.026   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.525   0.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.430   2.177   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.906   3.641   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.906   5.181   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.430   6.646   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.525   7.892   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.279   8.797   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.815   9.273   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.275   9.273   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.810   8.797   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.564   7.892   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.659   6.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.183   5.181   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.183   3.641   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.150   2.871   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.484   3.641   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.967   2.891   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.484   5.181   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.935   6.084   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.150   5.951   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.313   7.777   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.128   6.807   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.570   5.058   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.499   8.214   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.203   8.336   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.406   9.460   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.352  10.938   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.938   9.299   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.261  10.328   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.495  10.779   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.694  12.192   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       7.639  11.810   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.366  13.406   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       9.104  11.334   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.283  12.487   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      10.191  14.069   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       9.424   9.828   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      11.740   7.611   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      12.240   5.951   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      13.574   5.181   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      15.024   5.976   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      13.574   3.641   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      15.024   2.745   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      12.240   2.871   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      11.775   1.048   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      11.962   2.016   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      12.657   3.764   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      12.588   0.609   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      14.289   0.481   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      11.683  -0.637   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      12.390  -2.132   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      10.152  -0.476   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       8.772  -1.525   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       5.595  -1.956   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       4.451  -2.987   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       4.727  -4.613   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0       3.722  -5.839   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   66                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   25                                                  
CONECT    8    7                                                            
CONECT    9    5   10   65                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   64                                                  
CONECT   12   11   13   63                                                  
CONECT   13   12   14   57                                                  
CONECT   14   13   15   55                                                  
CONECT   15   14   16   50                                                  
CONECT   16   15   17   49                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   48                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   40                                                  
CONECT   22   21   23   39                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24    7   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31                                                            
CONECT   33   23   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   22                                                       
CONECT   40   21                                                            
CONECT   41   19   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   48                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   18                                                       
CONECT   49   16                                                            
CONECT   50   15   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   14   56                                                  
CONECT   56   55                                                            
CONECT   57   13   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   12                                                       
CONECT   64   11                                                            
CONECT   65    9   66                                                       
CONECT   66   65    2   67                                                  
CONECT   67   66   68                                                       
CONECT   68   67                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  148    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₀H₃₆O₂₈

Average Mass

964.7000 Da

Monoisotopic Mass

964.13931 Da

IUPAC Name

(10S,12R,13R,14S,32R,34S,37R)-3,4,5,13,14,20,21,22,25,26,27,33,34,42,43,44-hexadecahydroxy-12,35-bis(hydroxymethyl)-9,11,16,31,36,38-hexaoxaheptacyclo[38.4.0.0^{2,7}.0^{10,15}.0^{18,23}.0^{24,29}.0^{32,37}]tetratetraconta-1(40),2(7),3,5,18(23),19,21,24(29),25,27,41,43-dodecaene-8,17,30,39-tetrone

Traditional Name

CAS Registry Number

Not Available

SMILES

OCC1O[C@@H]2OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)C3OC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]2C(O)[C@@H]1O

InChI Identifier

InChI=1S/C40H36O28/c41-5-15-25(51)31(57)33-39(63-15)67-37(61)9-3-13(45)23(49)29(55)19(9)20-10(4-14(46)24(50)30(20)56)38(62)68-40-34(32(58)26(52)16(6-42)64-40)66-36(60)8-2-12(44)22(48)28(54)18(8)17-7(35(59)65-33)1-11(43)21(47)27(17)53/h1-4,15-16,25-26,31-34,39-58H,5-6H2/t15-,16?,25+,26-,31+,32?,33?,34-,39+,40-/m1/s1

InChI Key

HXCLCVSZIRHLDL-BRRUUAGESA-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
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
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
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

Description

This compound belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Biphenol
Tetracarboxylic acid or derivatives
Alkyl glycoside
Fatty alcohol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	-0.18	ChemAxon
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	487.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	213.06 m³·mol⁻¹	ChemAxon
Polarizability	83.56 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,1'; 2,2'-diHHDP-di-glucose (NP0333066)

MOL for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

3D MOL for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

3D SDF for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

3D-SDF for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

PDB for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

3D PDB for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

SMILES for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

INCHI for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

Structure for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)

3D Structure for NP0333066 (1,1'; 2,2'-diHHDP-di-glucose)