NP-MRD: Showing NP-Card for 3,8-Di-O-methylellagic acid (NP0138257)

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Record Information

Version

1.0

Created at

2022-05-31 17:17:29 UTC

Updated at

2022-05-31 17:17:29 UTC

NP-MRD ID

NP0138257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8-Di-O-methylellagic acid

Description

3,8-Di-O-methylellagic acid 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. 3,8-Di-O-methylellagic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
    4.8520   -0.2600    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803   -0.3018   -0.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9628    0.3196   -0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9610    1.6303   -0.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    2.3393   -1.1806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364    2.2532   -1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.5553   -0.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697    2.1190   -1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239    3.3138   -1.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    1.4312   -0.7644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.1914   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9536   -0.4922   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    0.0937   -0.2812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9050    0.7966    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9088   -1.8139    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750   -2.5208    0.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7119   -2.4851    0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580   -1.7763    0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948   -2.3307    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.5369    0.7963 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8012   -1.6451    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991   -0.3968   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5869    0.2387   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5738   -0.4614   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7286    0.4412    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016   -1.2686    1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2069    0.0913    1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0380    1.9029   -1.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6853    3.2980   -1.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4989    0.7280    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0842    1.8547    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9301    0.3235    0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9975   -2.1091    0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -3.5228    0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  2  0
 17 15  1  0
 15 16  1  0
 15 12  2  0
 12 13  1  0
 13 14  1  0
 12 11  1  0
 11 24  2  0
 24 23  1  0
 23  7  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  4  3  1  0
 23 22  1  0
 24 18  1  0
 10 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 17 34  1  0
 16 33  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
  6 29  1  0
  5 28  1  0
M  END


  Mrv1533004201504532D          

 24 27  0  0  0  0            999 V2000
    5.5539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 18 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0138257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=O)C3=CC(O)=C(OC)C4=C3C2=C(C=C1O)C(=O)O4

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O8/c1-21-11-7(17)3-5-9-10-6(15(19)23-13(9)11)4-8(18)12(22-2)14(10)24-16(5)20/h3-4,17-18H,1-2H3

> <INCHI_KEY>
KLAGYIBJNXLDTL-UHFFFAOYSA-N

> <FORMULA>
C16H10O8

> <MOLECULAR_WEIGHT>
330.248

> <EXACT_MASS>
330.037567282

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.392295719997367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,13-dihydroxy-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.30771053

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.564201137311579

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.879093554901259

> <JCHEM_PKA_STRONGEST_BASIC>
-4.689406592493416

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000002

> <JCHEM_REFRACTIVITY>
79.5722

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,13-dihydroxy-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.367  -1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.437  -2.874   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  O   UNK     0       1.127  -4.207   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.897  -5.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.747   1.127   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22    7   24                                                  
CONECT   24   23   11   18                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
3,8-Di-O-methylellagate	Generator
3,3'-Di-O-methylellagic acid	MeSH

Chemical Formula

C₁₆H₁₀O₈

Average Mass

330.2480 Da

Monoisotopic Mass

330.03757 Da

IUPAC Name

6,13-dihydroxy-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

Traditional Name

6,13-dihydroxy-7,14-dimethoxy-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4(16),5,7,11,13-hexaene-3,10-dione

CAS Registry Number

2239-88-5

SMILES

COC1=C2OC(=O)C3=CC(O)=C(OC)C4=C3C2=C(C=C1O)C(=O)O4

InChI Identifier

InChI=1S/C16H10O8/c1-21-11-7(17)3-5-9-10-6(15(19)23-13(9)11)4-8(18)12(22-2)14(10)24-16(5)20/h3-4,17-18H,1-2H3

InChI Key

KLAGYIBJNXLDTL-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

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) 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
Isocoumarin
Coumarin
Benzopyran
1-benzopyran
2-benzopyran
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen 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	2.55	ALOGPS
logP	1.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	5.88	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.57 m³·mol⁻¹	ChemAxon
Polarizability	30.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

5488919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,8-Di-O-methylellagic acid (NP0138257)

MOL for NP0138257 (3,8-Di-O-methylellagic acid)

3D MOL for NP0138257 (3,8-Di-O-methylellagic acid)

3D SDF for NP0138257 (3,8-Di-O-methylellagic acid)

3D-SDF for NP0138257 (3,8-Di-O-methylellagic acid)

PDB for NP0138257 (3,8-Di-O-methylellagic acid)

3D PDB for NP0138257 (3,8-Di-O-methylellagic acid)

SMILES for NP0138257 (3,8-Di-O-methylellagic acid)

INCHI for NP0138257 (3,8-Di-O-methylellagic acid)

Structure for NP0138257 (3,8-Di-O-methylellagic acid)

3D Structure for NP0138257 (3,8-Di-O-methylellagic acid)