NP-MRD: Showing NP-Card for Castacrenin C (NP0085481)

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Record Information

Version

2.0

Created at

2022-04-29 05:59:35 UTC

Updated at

2025-02-11 15:44:42 UTC

NP-MRD ID

NP0085481

Natural Product DOI

https://doi.org/10.57994/2360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Castacrenin C

Description

Castacrenin C 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. Castacrenin C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, castacrenin C has been detected, but not quantified in, nuts. Castacrenin C is found in Castanea crenata . Castacrenin C was first documented in 2024 (PMID: 38359463). This could make castacrenin C a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305242D          

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M  END

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    2.2539    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  1  2  0  0  0  0
  6  1  1  0  0  0  0
  7  3  1  0  0  0  0
  8  2  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 16  7  1  0  0  0  0
 17  6  2  0  0  0  0
 18  8  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  2  0  0  0  0
 20 12  1  0  0  0  0
 21 15  2  0  0  0  0
 21 19  1  0  0  0  0
 22 20  2  0  0  0  0
 23  9  2  0  0  0  0
 23 17  1  0  0  0  0
 24 13  2  0  0  0  0
 24 22  1  0  0  0  0
 25  5  1  0  0  0  0
 26 10  1  0  0  0  0
 27 14  1  0  0  0  0
 28  3  1  0  0  0  0
 29  6  1  0  0  0  0
 30  7  1  0  0  0  0
 31 15  1  0  0  0  0
 32 16  1  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
 35 19  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 38 22  1  0  0  0  0
 39 25  2  0  0  0  0
 40 26  2  0  0  0  0
 41 27  2  0  0  0  0
 42  8  1  0  0  0  0
 42 26  1  0  0  0  0
 43 24  1  0  0  0  0
 43 25  1  0  0  0  0
 44 23  1  0  0  0  0
 44 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)C(O)C(O)C1=CC2=C(C(=O)O1)C(=C(O)C(O)=C2O)C1=C2C(=O)OC3=C4C(=CC(O)=C3O)C(=O)OC(C(O)=C1O)=C24

> <INCHI_IDENTIFIER>
InChI=1S/C27H18O17/c28-3-7(30)16(32)18(34)8-2-4-10(26(40)42-8)11(19(35)21(37)15(4)31)12-14-13-9-5(25(39)43-24(13)22(38)20(12)36)1-6(29)17(33)23(9)44-27(14)41/h1-2,7,16,18,28-38H,3H2

> <INCHI_KEY>
AQPVDJOZILVCEZ-UHFFFAOYSA-N

> <FORMULA>
C27H18O17

> <MOLECULAR_WEIGHT>
614.4216

> <EXACT_MASS>
614.05439915

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
56.1090115544057

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7,13,14-tetrahydroxy-5-[5,6,7-trihydroxy-1-oxo-3-(1,2,3,4-tetrahydroxybutyl)-1H-isochromen-8-yl]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
0.3967542476666667

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.020674789763629

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.267661535474969

> <JCHEM_PKA_STRONGEST_BASIC>
-3.760494843789691

> <JCHEM_POLAR_SURFACE_AREA>
301.43

> <JCHEM_REFRACTIVITY>
142.36480000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,13,14-tetrahydroxy-5-[5,6,7-trihydroxy-1-oxo-3-(1,2,3,4-tetrahydroxybutyl)isochromen-8-yl]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.723  -5.541   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.113  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.183  -5.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.343  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.493  -4.207   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.127  -4.207   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.413  -6.875   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.803  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.033  -4.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.897  -5.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.127  -6.875   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.747   1.127   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.183  -2.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.207  -4.207   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -9.653  -1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.113  -4.207   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.183  -8.208   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.033  -1.540   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.803  -5.541   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.437  -6.256   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.358  -0.770   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.897  -8.208   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       6.517   2.461   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       3.437  -5.541   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -2.723  -2.874   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       4.207   1.127   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       5.747  -4.207   0.000  0.00  0.00           O+0
CONECT    1    5    6                                                       
CONECT    2    4    8                                                       
CONECT    3    7   28                                                       
CONECT    4    2   10   15                                                  
CONECT    5    1    9   25                                                  
CONECT    6    1   17   29                                                  
CONECT    7    3   16   30                                                  
CONECT    8    2   18   42                                                  
CONECT    9    5   13   23                                                  
CONECT   10    4   11   26                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   14   20                                                  
CONECT   13    9   14   24                                                  
CONECT   14   12   13   27                                                  
CONECT   15    4   21   31                                                  
CONECT   16    7   18   32                                                  
CONECT   17    6   23   33                                                  
CONECT   18    8   16   34                                                  
CONECT   19   11   21   35                                                  
CONECT   20   12   22   36                                                  
CONECT   21   15   19   37                                                  
CONECT   22   20   24   38                                                  
CONECT   23    9   17   44                                                  
CONECT   24   13   22   43                                                  
CONECT   25    5   39   43                                                  
CONECT   26   10   40   42                                                  
CONECT   27   14   41   44                                                  
CONECT   28    3                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   25                                                            
CONECT   40   26                                                            
CONECT   41   27                                                            
CONECT   42    8   26                                                       
CONECT   43   24   25                                                       
CONECT   44   23   27                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₁₈O₁₇

Average Mass

614.4216 Da

Monoisotopic Mass

614.05440 Da

IUPAC Name

6,7,13,14-tetrahydroxy-5-[5,6,7-trihydroxy-1-oxo-3-(1,2,3,4-tetrahydroxybutyl)-1H-isochromen-8-yl]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Traditional Name

6,7,13,14-tetrahydroxy-5-[5,6,7-trihydroxy-1-oxo-3-(1,2,3,4-tetrahydroxybutyl)isochromen-8-yl]-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

OCC(O)C(O)C(O)C1=CC2=C(C(=O)O1)C(=C(O)C(O)=C2O)C1=C2C(=O)OC3=C4C(=CC(O)=C3O)C(=O)OC(C(O)=C1O)=C24

InChI Identifier

InChI=1S/C27H18O17/c28-3-7(30)16(32)18(34)8-2-4-10(26(40)42-8)11(19(35)21(37)15(4)31)12-14-13-9-5(25(39)43-24(13)22(38)20(12)36)1-6(29)17(33)23(9)44-27(14)41/h1-2,7,16,18,28-38H,3H2

InChI Key

AQPVDJOZILVCEZ-UHFFFAOYSA-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
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
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
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
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

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

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
Castanea crenata	Plant	KNApSAcK
Castanea sativa		Not Available

Chemical Taxonomy

Description

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
Ellagic_acid
Biphenol
7,8-dihydroxycoumarin
Coumarin
Isocoumarin
Benzopyran
1-benzopyran
2-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Secondary alcohol
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic 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	1.63	ALOGPS
logP	0.4	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.27	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	301.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.36 m³·mol⁻¹	ChemAxon
Polarizability	56.11 Å³	ChemAxon
Number of Rings	6	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

HMDB0030633

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002537

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

85228592

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Castacrenin C (NP0085481)

MOL for NP0085481 (Castacrenin C)

3D MOL for NP0085481 (Castacrenin C)

3D SDF for NP0085481 (Castacrenin C)

3D-SDF for NP0085481 (Castacrenin C)

PDB for NP0085481 (Castacrenin C)

3D PDB for NP0085481 (Castacrenin C)

SMILES for NP0085481 (Castacrenin C)

INCHI for NP0085481 (Castacrenin C)

Structure for NP0085481 (Castacrenin C)

3D Structure for NP0085481 (Castacrenin C)