NP-MRD: Showing NP-Card for Castacrenin J (NP0333061)

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Record Information

Version

1.0

Created at

2024-05-04 05:06:42 UTC

Updated at

2024-05-06 00:11:04 UTC

NP-MRD ID

NP0333061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Castacrenin J

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01162307432D          

 54 61  0  0  1  0            999 V2000
    2.5122    2.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136    1.8808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2991    2.0118    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1720    2.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9079    3.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2697    4.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6996    4.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9142    5.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 22 51  1  0  0  0  0
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 49 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END


  Mrv2104 01162307432D          

 54 61  0  0  1  0            999 V2000
    2.5122    2.6032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0333061

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H](C2OC(=O)C4C3=C(O)C(=O)C43OC4=C(O)C(O)=CC(C(O)=O)=C4[C@H]23)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H22O21/c34-3-8-19(39)27-26-15-10-4(29(46)47)1-7(36)18(38)25(10)54-33(15)16(32(50)52-26)14(23(43)28(33)45)12-13(31(49)53-27)11(21(41)24(44)22(12)42)9-5(30(48)51-8)2-6(35)17(37)20(9)40/h1-2,8,15-16,19,26-27,34-44H,3H2,(H,46,47)/t8?,15-,16?,19-,26?,27?,33?/m1/s1

> <INCHI_KEY>
BXVKUXOMPYMAKS-ZOYKKVNDSA-N

> <FORMULA>
C33H22O21

> <MOLECULAR_WEIGHT>
754.518

> <EXACT_MASS>
754.065357728

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
65.24276509637548

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(15R,16S,18R)-2,3,4,7,8,9,15,22,23,28-decahydroxy-14-(hydroxymethyl)-12,27,31,34-tetraoxo-13,25,32,35-tetraoxaoctacyclo[14.13.3.3^{17,26}.0^{5,30}.0^{6,11}.0^{18,26}.0^{19,24}.0^{29,33}]pentatriaconta-1(30),2,4,6,8,10,19,21,23,28-decaene-20-carboxylic acid

> <JCHEM_LOGP>
-0.3703498496666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
6.482077822035943

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.705940030825792

> <JCHEM_PKA_STRONGEST_BASIC>
-4.820201605155464

> <JCHEM_POLAR_SURFACE_AREA>
365.03

> <JCHEM_REFRACTIVITY>
168.62329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(15R,16S,18R)-2,3,4,7,8,9,15,22,23,28-decahydroxy-14-(hydroxymethyl)-12,27,31,34-tetraoxo-13,25,32,35-tetraoxaoctacyclo[14.13.3.3^{17,26}.0^{5,30}.0^{6,11}.0^{18,26}.0^{19,24}.0^{29,33}]pentatriaconta-1(30),2,4,6,8,10,19,21,23,28-decaene-20-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       4.689   4.859   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.945   3.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.425   3.755   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.188   5.277   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.561   5.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.237   7.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.173   8.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.573   9.923   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.486  11.013   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.061  10.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.149   9.229   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.636   9.629   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.758   7.754   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.725   6.555   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.246   6.792   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.802   8.229   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.213   5.593   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.734   5.830   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.657   4.157   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.624   2.958   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.066   3.270   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.169   5.119   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.462  11.806   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.953   5.313   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.927   4.139   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.400   4.587   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.748   6.087   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.221   6.536   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.198   5.190   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.150   6.690   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.169   7.485   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.333   6.476   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.861   6.666   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.461   8.084   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.789   5.437   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.318   5.627   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.189   4.019   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.661   3.829   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.061   2.411   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.533   2.221   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.989   1.182   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.733   5.058   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.623   7.139   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.652   8.679   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.196   9.182   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.252  10.655   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.732   7.953   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.272   7.982   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.059   2.246   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.580   2.483   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       7.136   3.920   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.506   3.217   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       4.535   0.798   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       5.527  -0.380   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   49                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   44                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   23                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   14   51                                                  
CONECT   23   10                                                            
CONECT   24    5                                                            
CONECT   25    3   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   43                                                  
CONECT   28   27                                                            
CONECT   29   25   30   42                                                  
CONECT   30   29   31   43   47                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   42                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   42                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   38   32   29                                                  
CONECT   43   30   27   44                                                  
CONECT   44   43    7   45                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   30   45   48                                                  
CONECT   48   47                                                            
CONECT   49    2   50   53                                                  
CONECT   50   49   51                                                       
CONECT   51   50   22   52                                                  
CONECT   52   51                                                            
CONECT   53   49   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₂O₂₁

Average Mass

754.5180 Da

Monoisotopic Mass

754.06536 Da

IUPAC Name

(15R,16S,18R)-2,3,4,7,8,9,15,22,23,28-decahydroxy-14-(hydroxymethyl)-12,27,31,34-tetraoxo-13,25,32,35-tetraoxaoctacyclo[14.13.3.3^{17,26}.0^{5,30}.0^{6,11}.0^{18,26}.0^{19,24}.0^{29,33}]pentatriaconta-1(30),2,4,6,8,10,19,21,23,28-decaene-20-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

OCC1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C(O)C(O)=C(O)C3=C2C(=O)O[C@H](C2OC(=O)C4C3=C(O)C(=O)C43OC4=C(O)C(O)=CC(C(O)=O)=C4[C@H]23)[C@@H]1O

InChI Identifier

InChI=1S/C33H22O21/c34-3-8-19(39)27-26-15-10-4(29(46)47)1-7(36)18(38)25(10)54-33(15)16(32(50)52-26)14(23(43)28(33)45)12-13(31(49)53-27)11(21(41)24(44)22(12)42)9-5(30(48)51-8)2-6(35)17(37)20(9)40/h1-2,8,15-16,19,26-27,34-44H,3H2,(H,46,47)/t8?,15-,16?,19-,26?,27?,33?/m1/s1

InChI Key

BXVKUXOMPYMAKS-ZOYKKVNDSA-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
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, C3D6O, 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	-0.37	ChemAxon
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	365.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	168.62 m³·mol⁻¹	ChemAxon
Polarizability	65.24 Å³	ChemAxon
Number of Rings	8	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 Castacrenin J (NP0333061)

MOL for NP0333061 (Castacrenin J)

3D MOL for NP0333061 (Castacrenin J)

3D SDF for NP0333061 (Castacrenin J)

3D-SDF for NP0333061 (Castacrenin J)

PDB for NP0333061 (Castacrenin J)

3D PDB for NP0333061 (Castacrenin J)

SMILES for NP0333061 (Castacrenin J)

INCHI for NP0333061 (Castacrenin J)

Structure for NP0333061 (Castacrenin J)

3D Structure for NP0333061 (Castacrenin J)