NP-MRD: Showing NP-Card for Dehydrodicatechin A (NP0056484)

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Record Information

Version

2.0

Created at

2022-04-28 02:15:38 UTC

Updated at

2022-04-28 02:15:38 UTC

NP-MRD ID

NP0056484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydrodicatechin A

Description

Dehydrodicatechin A is found in Prunus grayana.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204152D          

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M  END

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 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 17 19  1  0  0  0  0
  9 19  1  6  0  0  0
 17 20  1  6  0  0  0
 13 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 30 32  1  6  0  0  0
 29 33  1  6  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  0  0  0  0
 36 40  1  0  0  0  0
 25 41  1  0  0  0  0
  2 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@]34C[C@](O)(O[C@@H]5CC6=C(O)C=C(O)C=C6O[C@H]35)C(=O)C=C14)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c31-12-4-17(33)13-7-23-28(39-21(13)5-12)29-10-30(38,42-23)24(37)8-15(29)25-22(41-29)9-18(34)14-6-20(36)26(40-27(14)25)11-1-2-16(32)19(35)3-11/h1-5,8-9,20,23,26,28,31-36,38H,6-7,10H2/t20-,23+,26-,28-,29-,30-/m0/s1

> <INCHI_KEY>
XNGZKGIFXTWBFN-HXRUGMRDSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.51

> <EXACT_MASS>
576.126776213

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.003749570658826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,8S,9S,16S,18R,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.0^{1,13}.0^{3,12}.0^{6,11}.0^{18,27}.0^{20,25}]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
3.078138104333334

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.23010349204916

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.756866051450961

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2934060661760975

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
141.8091

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,9S,16S,18R,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.0^{1,13}.0^{3,12}.0^{6,11}.0^{18,27}.0^{20,25}]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.700   1.164   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.784  -0.074   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.254   0.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.639   1.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.555   2.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.085   2.576   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.001   3.815   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.940   4.162   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.410   4.336   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.495   3.098   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.109   1.686   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.789   3.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.167   3.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.508   4.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.484   6.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.091   7.508   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.072   5.868   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.928   4.449   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.667   5.742   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.234   7.399   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.557   1.966   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.469   0.818   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.871   1.475   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.013  -0.645   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.521  -0.959   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.547   0.189   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.065   1.652   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.091   2.801   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.598   2.487   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.080   1.024   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.054  -0.125   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.588   0.710   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.624   3.635   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.132   3.321   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.157   4.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.676   5.933   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.168   6.247   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.142   5.098   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.686   7.709   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -8.701   7.081   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -2.003  -2.422   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       8.399  -1.486   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   42                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13   18   23                                             
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17   12                                                       
CONECT   19   17    9                                                       
CONECT   20   17                                                            
CONECT   21   13   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   12                                                       
CONECT   24   22   25                                                       
CONECT   25   24   26   41                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   21   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30   26                                                       
CONECT   32   30                                                            
CONECT   33   29   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37   33                                                       
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   25                                                            
CONECT   42    2                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5100 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

(1S,8S,9S,16S,18R,27S)-9-(3,4-dihydroxyphenyl)-5,8,16,21,23-pentahydroxy-2,10,17,26-tetraoxaheptacyclo[14.11.1.0^{1,13}.0^{3,12}.0^{6,11}.0^{18,27}.0^{20,25}]octacosa-3(12),4,6(11),13,20,22,24-heptaen-15-one

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O[C@H]1C1=CC=C(O)C(O)=C1)C1=C(O[C@]34C[C@](O)(O[C@@H]5CC6=C(O)C=C(O)C=C6O[C@H]35)C(=O)C=C14)C=C2O

InChI Identifier

InChI=1S/C30H24O12/c31-12-4-17(33)13-7-23-28(39-21(13)5-12)29-10-30(38,42-23)24(37)8-15(29)25-22(41-29)9-18(34)14-6-20(36)26(40-27(14)25)11-1-2-16(32)19(35)3-11/h1-5,8-9,20,23,26,28,31-36,38H,6-7,10H2/t20-,23+,26-,28-,29-,30-/m0/s1

InChI Key

XNGZKGIFXTWBFN-HXRUGMRDSA-N

Experimental Spectra

Not Available

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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Prunus grayana	Plant	KNApSAcK

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	2.37	ALOGPS
logP	3.08	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	141.81 m³·mol⁻¹	ChemAxon
Polarizability	57 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

Not Available

Showing NP-Card for Dehydrodicatechin A (NP0056484)

MOL for NP0056484 (Dehydrodicatechin A)

3D MOL for NP0056484 (Dehydrodicatechin A)

3D SDF for NP0056484 (Dehydrodicatechin A)

3D-SDF for NP0056484 (Dehydrodicatechin A)

PDB for NP0056484 (Dehydrodicatechin A)

3D PDB for NP0056484 (Dehydrodicatechin A)

SMILES for NP0056484 (Dehydrodicatechin A)

INCHI for NP0056484 (Dehydrodicatechin A)

Structure for NP0056484 (Dehydrodicatechin A)

3D Structure for NP0056484 (Dehydrodicatechin A)