NP-MRD: Showing NP-Card for Hexahydroxydiphenic acid (NP0084097)

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Record Information

Version

2.0

Created at

2022-04-29 04:56:16 UTC

Updated at

2022-04-29 04:56:16 UTC

NP-MRD ID

NP0084097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hexahydroxydiphenic acid

Description

4,4',5,5',6,6'-Hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid, also known as hexahydroxydiphenate, 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. 4,4',5,5',6,6'-Hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by EC.3.1.1.20 Enzyme via a hydrolysis-of-glycosylated-condensed-galloyl-groups-pattern1 reaction. 4,4',5,5',6,6'-Hexahydroxy--2,2'-dicarboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclotricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate. Hexahydroxydiphenic acid is found in Pistacia lentiscus and Punica granatum L. . This hydrolysis-of-glycosylated-condensed-galloyl-groups-pattern1 occurs in human gut microbiota.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -1.3129   -2.8010   -1.9200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -1.9181   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -1.9005   -1.3918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695   -0.9267   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7502   -0.9680   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668   -0.0394    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540   -0.0887    0.3409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666    0.9325    0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    1.9163    1.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3767    0.9623    0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6947    1.9663    1.5755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6675    0.0497    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7698    0.0560    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867    0.7656   -0.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6186    1.5156   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2056    2.1485   -2.8020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7503    1.5188   -1.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863    0.7530   -1.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606    0.0571   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448    0.0321   -0.1663 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202   -0.6601    0.8931 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939   -1.3547    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5611   -0.6537    0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244   -1.3738    1.9797 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946   -1.9574   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2865   -1.7266   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4345    0.5398    0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3826    1.9396    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    2.6445    2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770    1.5736   -2.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693    1.3109   -1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4800   -0.4928    0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.9123    2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4208   -1.9084    2.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 23  2  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 19  2  0
 19 20  1  0
 19 18  1  0
 18 14  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 12  4  1  0
 14 13  1  0
  3 25  1  0
  5 26  1  0
  7 27  1  0
  9 28  1  0
 11 29  1  0
 24 34  1  0
 22 33  1  0
 20 32  1  0
 18 31  1  0
 17 30  1  0
M  END


  Mrv1652308201908142D          

 24 25  0  0  0  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -0.7537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789    2.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  2  0  0  0  0
 22 13  1  0  0  0  0
 23 14  2  0  0  0  0
 24 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084097

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C(O)C=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24)

> <INCHI_KEY>
MFTSECOLKFLUSD-UHFFFAOYSA-N

> <FORMULA>
C14H10O10

> <MOLECULAR_WEIGHT>
338.224

> <EXACT_MASS>
338.027396522

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.06758109702458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.114245064

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8214364211298726

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1694004125905217

> <JCHEM_PKA_STRONGEST_BASIC>
-6.05340389399202

> <JCHEM_POLAR_SURFACE_AREA>
195.98

> <JCHEM_REFRACTIVITY>
77.592

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.041  -1.407   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.707   5.257   0.000  0.00  0.00           O+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7   13                                                  
CONECT    4    2    8   14                                                  
CONECT    5    1    9   15                                                  
CONECT    6    2   10   16                                                  
CONECT    7    3    8   11                                                  
CONECT    8    4    7   12                                                  
CONECT    9    5   11   17                                                  
CONECT   10    6   12   18                                                  
CONECT   11    7    9   19                                                  
CONECT   12    8   10   20                                                  
CONECT   13    3   21   22                                                  
CONECT   14    4   23   24                                                  
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
4,4',5,5',6,6'-Hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylate	Generator
Hexahydroxydiphenate	HMDB

Chemical Formula

C₁₄H₁₀O₁₀

Average Mass

338.2240 Da

Monoisotopic Mass

338.02740 Da

IUPAC Name

4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid

Traditional Name

4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C(O)=C1C1=C(O)C(O)=C(O)C=C1C(O)=O

InChI Identifier

InChI=1S/C14H10O10/c15-5-1-3(13(21)22)7(11(19)9(5)17)8-4(14(23)24)2-6(16)10(18)12(8)20/h1-2,15-20H,(H,21,22)(H,23,24)

InChI Key

MFTSECOLKFLUSD-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
Pistacia lentiscus	LOTUS Database	35616633
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
Biphenol
Biphenyl
Gallic acid or derivatives
Gallic acid
Hydroxybenzoic acid
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.13	ALOGPS
logP	1.11	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	195.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.59 m³·mol⁻¹	ChemAxon
Polarizability	29.07 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0126632

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8490515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexahydroxydiphenic acid

METLIN ID

Not Available

PubChem Compound

10315050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hexahydroxydiphenic acid (NP0084097)

MOL for NP0084097 (Hexahydroxydiphenic acid)

3D MOL for NP0084097 (Hexahydroxydiphenic acid)

3D SDF for NP0084097 (Hexahydroxydiphenic acid)

3D-SDF for NP0084097 (Hexahydroxydiphenic acid)

PDB for NP0084097 (Hexahydroxydiphenic acid)

3D PDB for NP0084097 (Hexahydroxydiphenic acid)

SMILES for NP0084097 (Hexahydroxydiphenic acid)

INCHI for NP0084097 (Hexahydroxydiphenic acid)

Structure for NP0084097 (Hexahydroxydiphenic acid)

3D Structure for NP0084097 (Hexahydroxydiphenic acid)