NP-MRD: Showing NP-Card for Di-O-methylbergenin (NP0138752)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-06-29 18:34:33 UTC

Updated at

2022-06-29 18:34:33 UTC

NP-MRD ID

NP0138752

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Di-O-methylbergenin

Description

Di-O-methylbergenin belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. It was first documented in 2002 (PMID: 12182600). Based on a literature review very few articles have been published on Di-O-methylbergenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    5.3658   -1.4735    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6748   -0.3182    0.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -0.3982   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6070   -1.5695    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2344   -1.6659    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802   -0.5248   -0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2630    0.6542   -0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6431    1.8266   -1.0184 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1942    2.7413   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6447    0.7460   -0.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582    1.9202   -0.6630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522    2.8969    0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8624   -0.5934   -0.5422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5562    0.5111   -0.0679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8511    0.5961   -0.4687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5455    1.6111    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4287    1.1114    1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6412   -0.6712   -0.4093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7100   -0.5460   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8589   -1.9060   -0.6875 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4834   -3.0462   -0.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -1.7808    0.0587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8268   -2.9592    0.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5388   -2.9286    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2024   -3.9321    0.6918 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4717   -1.3343    0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2258   -1.6459    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -2.3709   -0.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -2.4779    0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2058    2.3260    0.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    3.1131   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8943    3.6256   -0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7658    2.8505    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4820    3.9401   -0.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1659    2.7397    1.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -0.6054   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9125    1.0053   -1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6344    1.6031    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1127    2.6169    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    1.3394    2.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1130   -0.7657    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6393    0.2605   -1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6001   -1.9873   -1.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4146   -3.0235   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8385   -1.5108    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 10  2  0
 10 11  1  0
 11 12  1  0
 10  7  1  0
  7  8  1  0
  8  9  1  0
  7  6  2  0
  6 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24  5  1  0
  5  4  2  0
  4  3  1  0
  5  6  1  0
 22 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 13 36  1  6
 15 37  1  6
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  1
 19 42  1  0
 20 43  1  6
 21 44  1  0
 22 45  1  1
  4 29  1  0
M  END


  Mrv1652306292220342D          

 25 27  0  0  1  0            999 V2000
   -1.3480   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.2059    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
  5  6  2  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  1  0  0  0
 11 13  1  1  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138752

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O9/c1-21-7-4-6-9(13(23-3)12(7)22-2)14-15(25-16(6)20)11(19)10(18)8(5-17)24-14/h4,8,10-11,14-15,17-19H,5H2,1-3H3/t8-,10-,11+,14+,15-/m1/s1

> <INCHI_KEY>
RGHGUQJYNLPWPT-MUVVKYGDSA-N

> <FORMULA>
C16H20O9

> <MOLECULAR_WEIGHT>
356.327

> <EXACT_MASS>
356.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.63711883482053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R,5S,6S,7R)-5,6-dihydroxy-4-(hydroxymethyl)-12,13,14-trimethoxy-3,8-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(14),10,12-trien-9-one

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.935034853333333

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.046319170480196

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.735270240763555

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791924019618365

> <JCHEM_POLAR_SURFACE_AREA>
123.91000000000003

> <JCHEM_REFRACTIVITY>
82.32990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R,5S,6S,7R)-5,6-dihydroxy-4-(hydroxymethyl)-12,13,14-trimethoxy-3,8-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1(14),10,12-trien-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.746  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.184  -5.184   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.494  -6.517   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.034  -6.517   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.034  -3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.494  -1.183   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874  -1.183   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.104   0.151   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.874  -6.517   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564  -7.851   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    6   21                                                  
CONECT   21   20    3                                                       
CONECT   22    5   23                                                       
CONECT   23   22                                                            
CONECT   24    4   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₉

Average Mass

356.3270 Da

Monoisotopic Mass

356.11073 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

33815-57-5

SMILES

COC1=C(OC)C(OC)=C2[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C2=C1

InChI Identifier

InChI=1S/C16H20O9/c1-21-7-4-6-9(13(23-3)12(7)22-2)14-15(25-16(6)20)11(19)10(18)8(5-17)24-14/h4,8,10-11,14-15,17-19H,5H2,1-3H3/t8-,10-,11+,14+,15-/m1/s1

InChI Key

RGHGUQJYNLPWPT-MUVVKYGDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
Benzopyran
Isochromane
2-benzopyran
Anisole
Alkyl aryl ether
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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

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

9535184

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11360257

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Herzner H, Palmacci ER, Seeberger PH: Short total synthesis of 8,10-di-O-methylbergenin. Org Lett. 2002 Aug 22;4(17):2965-7. doi: 10.1021/ol026378e. [PubMed:12182600 ]

Showing NP-Card for Di-O-methylbergenin (NP0138752)

MOL for NP0138752 (Di-O-methylbergenin)

3D MOL for NP0138752 (Di-O-methylbergenin)

3D SDF for NP0138752 (Di-O-methylbergenin)

3D-SDF for NP0138752 (Di-O-methylbergenin)

PDB for NP0138752 (Di-O-methylbergenin)

3D PDB for NP0138752 (Di-O-methylbergenin)

SMILES for NP0138752 (Di-O-methylbergenin)

INCHI for NP0138752 (Di-O-methylbergenin)

Structure for NP0138752 (Di-O-methylbergenin)

3D Structure for NP0138752 (Di-O-methylbergenin)