NP-MRD: Showing NP-Card for ent-Gallocatechin 4'-methyl ether (NP0056078)

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Record Information

Version

2.0

Created at

2022-04-28 01:57:53 UTC

Updated at

2022-04-28 01:57:53 UTC

NP-MRD ID

NP0056078

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-Gallocatechin 4'-methyl ether

Description

Ent-gallocatechin 4'-methyl ether belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety. ent-Gallocatechin 4'-methyl ether is found in Cassia trachypus, Flemingia macrophylla and Panda oleosa. Based on a literature review very few articles have been published on Ent-gallocatechin 4'-methyl ether.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    5.0574    1.4511    1.9662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6641    1.9345    0.7104 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720    1.6295    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1900    0.4614   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -0.3668   -0.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948    0.1885   -0.8760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8211    1.0072   -0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5064    0.6310   -1.0928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5228    0.8038   -0.1230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -0.2673    0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769   -0.3427    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6759   -1.3805    1.9499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2182   -1.4494    3.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9490   -2.3960    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4012   -2.3334   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -3.3745   -1.0838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6013   -1.2829   -0.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -1.1722   -1.9726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5530   -0.7163   -1.7403 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0458   -0.6961   -2.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0765    2.1525    0.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370    2.4716    0.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5282    3.6466    1.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1568    1.3758    2.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5921    0.4646    2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    2.1727    2.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0969   -1.2099   -1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891   -0.7365   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7612    1.3746   -1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.4721    2.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1359   -1.0479    3.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5709   -3.2470    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3741   -3.4326   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672   -0.3528   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -2.1303   -2.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0656   -1.4491   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525    0.1045   -3.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135    2.7911    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    4.2515    1.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7 21  1  0
 21 22  2  0
 22 23  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 22  3  1  0
 19  8  1  0
 17 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 21 38  1  0
 23 39  1  0
  8 29  1  6
 11 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  1
 20 37  1  0
M  END


  Mrv1652304282203572D          

 23 25  0  0  1  0            999 V2000
   -0.7145   -0.4125    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   -1.6500    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
    0.7145   -0.4125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  6  0  0  0
  8 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  1  0  0  0  0
  3 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056078

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1O)[C@@H]1OC2=CC(O)=CC(O)=C2C[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-22-16-11(19)2-7(3-12(16)20)15-13(21)6-9-10(18)4-8(17)5-14(9)23-15/h2-5,13,15,17-21H,6H2,1H3/t13-,15+/m1/s1

> <INCHI_KEY>
ITDYPNOEEHONAH-HIFRSBDPSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.297

> <EXACT_MASS>
320.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.887015953224637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.6374357496666665

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.780916474540735

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20276510661502

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2955029860354976

> <JCHEM_POLAR_SURFACE_AREA>
119.61000000000001

> <JCHEM_REFRACTIVITY>
80.4629

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   23                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15   20                                                       
CONECT   20   19                                                            
CONECT   21   14                                                            
CONECT   22    3                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₇

Average Mass

320.2970 Da

Monoisotopic Mass

320.08960 Da

IUPAC Name

(2S,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

(2S,3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1O)[C@@H]1OC2=CC(O)=CC(O)=C2C[C@H]1O

InChI Identifier

InChI=1S/C16H16O7/c1-22-16-11(19)2-7(3-12(16)20)15-13(21)6-9-10(18)4-8(17)5-14(9)23-15/h2-5,13,15,17-21H,6H2,1H3/t13-,15+/m1/s1

InChI Key

ITDYPNOEEHONAH-HIFRSBDPSA-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
Cassia trachypus	Plant	KNApSAcK
Flemingia macrophylla	LOTUS Database	35616633
Panda oleosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epigallocatechins. Epigallocatechins are compounds containing epigallocatechin or a derivative. Epigallocatechin is a flavan-3-ol containing a benzopyran-3,5,7-triol linked to a 3,4,5-hydroxyphenyl moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Epigallocatechins

Alternative Parents

Substituents

Epigallocatechin
4p-methoxyflavonoid-skeleton
7-hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Resorcinol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Ether
Polyol
Oxacycle
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020135 )

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	0.98	ALOGPS
logP	1.64	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.2	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	119.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.46 m³·mol⁻¹	ChemAxon
Polarizability	31.89 Å³	ChemAxon
Number of Rings	3	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

C00008821

Chemspider ID

8262882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10087345

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ent-Gallocatechin 4'-methyl ether (NP0056078)

MOL for NP0056078 (ent-Gallocatechin 4'-methyl ether)

3D MOL for NP0056078 (ent-Gallocatechin 4'-methyl ether)

3D SDF for NP0056078 (ent-Gallocatechin 4'-methyl ether)

3D-SDF for NP0056078 (ent-Gallocatechin 4'-methyl ether)

PDB for NP0056078 (ent-Gallocatechin 4'-methyl ether)

3D PDB for NP0056078 (ent-Gallocatechin 4'-methyl ether)

SMILES for NP0056078 (ent-Gallocatechin 4'-methyl ether)

INCHI for NP0056078 (ent-Gallocatechin 4'-methyl ether)

Structure for NP0056078 (ent-Gallocatechin 4'-methyl ether)

3D Structure for NP0056078 (ent-Gallocatechin 4'-methyl ether)