NP-MRD: Showing NP-Card for Gallagic acid (NP0084011)

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Record Information

Version

2.0

Created at

2022-04-29 04:52:48 UTC

Updated at

2022-04-29 04:52:48 UTC

NP-MRD ID

NP0084011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gallagic acid

Description

65995-62-2 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) 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. Gallagic acid is found in Punica granatum . 65995-62-2 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500432D          

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    5.5539    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004261500432D          

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  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  2  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 28 34  2  0  0  0  0
 23 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  2  0  0  0  0
 35 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C2OC(=O)C3=C(C(O)=C(O)C4=C3C2=C1C(=O)O4)C1=C(O)C(O)=C(O)C=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H14O18/c29-5-1-3(25(39)40)7(17(33)15(5)31)9-13-11-12-14(28(44)46-23(11)21(37)19(9)35)10(20(36)22(38)24(12)45-27(13)43)8-4(26(41)42)2-6(30)16(32)18(8)34/h1-2,29-38H,(H,39,40)(H,41,42)

> <INCHI_KEY>
ZASJRRFAYSNSHU-UHFFFAOYSA-N

> <FORMULA>
C28H14O18

> <MOLECULAR_WEIGHT>
638.402

> <EXACT_MASS>
638.018013611

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
56.46957766929364

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[12-(6-carboxy-2,3,4-trihydroxyphenyl)-6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl]-3,4,5-trihydroxybenzoic acid

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
3.1041470279999994

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.753676375740735

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1574209248547116

> <JCHEM_PKA_STRONGEST_BASIC>
-4.81546813165419

> <JCHEM_POLAR_SURFACE_AREA>
329.5

> <JCHEM_REFRACTIVITY>
147.27779999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gallagic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0      10.829  -1.078   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.677  -0.206   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.137   2.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.367   3.795   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.137   5.128   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.827   3.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.057   5.128   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.057   2.461   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.055   1.999   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.827   1.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.747  -4.207   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.745  -4.669   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.975  -5.079   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.207   1.127   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.747   1.127   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.517   2.461   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.127  -4.207   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.413  -4.207   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.183  -2.874   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.183  -5.541   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.723  -5.541   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.413  -6.875   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.183  -8.208   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.127  -6.875   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.897  -5.541   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.437  -5.541   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       4.207  -6.875   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   34                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   13   33                                                  
CONECT   33   32   18   34                                                  
CONECT   34   33   22   28                                                  
CONECT   35   23   36   43                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42   35   44                                                  
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₁₄O₁₈

Average Mass

638.4020 Da

Monoisotopic Mass

638.01801 Da

IUPAC Name

2-[12-(6-carboxy-2,3,4-trihydroxyphenyl)-6,7,13,14-tetrahydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaen-5-yl]-3,4,5-trihydroxybenzoic acid

Traditional Name

gallagic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C2OC(=O)C3=C(C(O)=C(O)C4=C3C2=C1C(=O)O4)C1=C(O)C(O)=C(O)C=C1C(O)=O

InChI Identifier

InChI=1S/C28H14O18/c29-5-1-3(25(39)40)7(17(33)15(5)31)9-13-11-12-14(28(44)46-23(11)21(37)19(9)35)10(20(36)22(38)24(12)45-27(13)43)8-4(26(41)42)2-6(30)16(32)18(8)34/h1-2,29-38H,(H,39,40)(H,41,42)

InChI Key

ZASJRRFAYSNSHU-UHFFFAOYSA-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
Punica granatum	Plant	KNApSAcK

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) 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
Gallic acid or derivatives
Gallic acid
Coumarin
Isocoumarin
Hydroxybenzoic acid
Benzopyran
2-benzopyran
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Benzoic acid
Pyrogallol derivative
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.87	ALOGPS
logP	3.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	329.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	147.28 m³·mol⁻¹	ChemAxon
Polarizability	56.47 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

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

14754405

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gallagic acid (NP0084011)

MOL for NP0084011 (Gallagic acid)

3D MOL for NP0084011 (Gallagic acid)

3D SDF for NP0084011 (Gallagic acid)

3D-SDF for NP0084011 (Gallagic acid)

PDB for NP0084011 (Gallagic acid)

3D PDB for NP0084011 (Gallagic acid)

SMILES for NP0084011 (Gallagic acid)

INCHI for NP0084011 (Gallagic acid)

Structure for NP0084011 (Gallagic acid)

3D Structure for NP0084011 (Gallagic acid)