NP-MRD: Showing NP-Card for Vescalagin carboxylic acid (NP0333053)

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Record Information

Version

1.0

Created at

2024-05-04 04:23:49 UTC

Updated at

2024-05-06 00:10:56 UTC

NP-MRD ID

NP0333053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vescalagin carboxylic acid

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162307002D          

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M  END


  Mrv2104 01162307002D          

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 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  2  0  0  0  0
  2 68  1  0  0  0  0
 68 69  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[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/C42H26O27/c43-8-1-5-12(25(49)22(8)46)13-6(2-9(44)23(47)26(13)50)40(62)67-34-11(4-65-38(5)60)66-39(61)7-3-10(45)24(48)27(51)14(7)15-19-16(29(53)32(56)28(15)52)17-20-18(31(55)33(57)30(17)54)21(37(58)59)35(68-41(20)63)36(34)69-42(19)64/h1-3,11,21,34-36,43-57H,4H2,(H,58,59)/t11-,21+,34-,35?,36+/m1/s1

> <INCHI_KEY>
ZTOKIAYQNMCRRX-RJNQDSEGSA-N

> <FORMULA>
C42H26O27

> <MOLECULAR_WEIGHT>
962.643

> <EXACT_MASS>
962.066145577

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
82.5272565694992

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <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-4,17,22,40,44-pentaoxo-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-46-carboxylic acid

> <JCHEM_LOGP>
2.3235816993333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
6.946041982365034

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.919850049089646

> <JCHEM_PKA_STRONGEST_BASIC>
-6.177314993937118

> <JCHEM_POLAR_SURFACE_AREA>
472.2500000000001

> <JCHEM_REFRACTIVITY>
217.56490000000008

> <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-4,17,22,40,44-pentaoxo-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-46-carboxylic acid

> <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       4.851  -8.084   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.682  -9.636   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.131  -5.519   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.132  -4.388   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.622  -4.503   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.257  -3.239   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.888  -4.014   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.793  -2.819   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.170  -2.710   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.488  -2.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.721  -3.842   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.150  -3.127   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.390  -4.040   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.405  -1.586   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.177  -0.648   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.431   0.871   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.698  -1.140   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.462  -0.018   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.523   1.165   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.047   1.386   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.009   2.610   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.976   3.794   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.527   2.872   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.059   4.317   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.512   1.689   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.980   0.244   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.837  -1.018   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.214  -1.170   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.260  -3.170   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.909  -4.567   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.209  -5.392   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.749  -5.382   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.832  -6.920   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.205  -7.618   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.287  -9.155   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.495  -6.777   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.413  -5.239   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      12.703  -4.399   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      10.040  -4.542   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      10.671  -3.137   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.104  -3.701   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      13.470  -4.412   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      13.309  -2.742   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      14.742  -3.306   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      13.080  -1.219   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      14.285  -0.260   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      11.647  -0.655   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      10.443  -1.614   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      12.868  -7.475   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       6.784  -6.872   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       5.470  -1.644   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       5.045  -0.099   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       3.548   0.315   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       3.721   1.845   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       6.472  -0.474   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0       7.947  -0.032   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0       9.427  -0.457   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      10.252   0.844   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -0.002  -5.858   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -1.548  -5.570   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -2.346  -6.956   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -3.886  -6.926   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      -1.618  -8.344   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      -2.467  -9.629   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   68                                                  
CONECT    3    2    4   64                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   64                                                  
CONECT   11   10                                                            
CONECT   12    8   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   65                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   32                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   23   58                                                  
CONECT   32   19                                                            
CONECT   33   14                                                            
CONECT   34   12   35   56                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   55                                                  
CONECT   37   36   38   44                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   54                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   37   45                                                  
CONECT   45   44   46   53                                                  
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   45   62                                                  
CONECT   54   41                                                            
CONECT   55   36                                                            
CONECT   56   34   57   60                                                  
CONECT   57   56   58                                                       
CONECT   58   57   31   59                                                  
CONECT   59   58                                                            
CONECT   60   56   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   53   63                                                  
CONECT   63   62                                                            
CONECT   64    3   10   65                                                  
CONECT   65   64   16   66                                                  
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66    2   69                                                  
CONECT   69   68                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  154    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₂₆O₂₇

Average Mass

962.6430 Da

Monoisotopic Mass

962.06615 Da

IUPAC Name

(1R,2R,20R,42S,46S)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37-pentadecahydroxy-4,17,22,40,44-pentaoxo-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-46-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

OC(=O)[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/C42H26O27/c43-8-1-5-12(25(49)22(8)46)13-6(2-9(44)23(47)26(13)50)40(62)67-34-11(4-65-38(5)60)66-39(61)7-3-10(45)24(48)27(51)14(7)15-19-16(29(53)32(56)28(15)52)17-20-18(31(55)33(57)30(17)54)21(37(58)59)35(68-41(20)63)36(34)69-42(19)64/h1-3,11,21,34-36,43-57H,4H2,(H,58,59)/t11-,21+,34-,35?,36+/m1/s1

InChI Key

ZTOKIAYQNMCRRX-RJNQDSEGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, C2D6OS, 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, CDCl₃, 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	2.32	ChemAxon
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	472.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	217.56 m³·mol⁻¹	ChemAxon
Polarizability	82.53 Å³	ChemAxon
Number of Rings	9	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 Vescalagin carboxylic acid (NP0333053)

MOL for NP0333053 (Vescalagin carboxylic acid)

3D MOL for NP0333053 (Vescalagin carboxylic acid)

3D SDF for NP0333053 (Vescalagin carboxylic acid)

3D-SDF for NP0333053 (Vescalagin carboxylic acid)

PDB for NP0333053 (Vescalagin carboxylic acid)

3D PDB for NP0333053 (Vescalagin carboxylic acid)

SMILES for NP0333053 (Vescalagin carboxylic acid)

INCHI for NP0333053 (Vescalagin carboxylic acid)

Structure for NP0333053 (Vescalagin carboxylic acid)

3D Structure for NP0333053 (Vescalagin carboxylic acid)