NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0329468)

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Record Information

Version

2.0

Created at

2022-09-12 13:52:12 UTC

Updated at

2022-09-12 13:52:12 UTC

NP-MRD ID

NP0329468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

4'-O-methylrobinetinidol 3'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 4'-O-methylrobinetinidol 3'-O-beta-D-glucopyranoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Acacia mearnsii. (2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol was first documented in 2011 (PMID: 21192716). Based on a literature review very few articles have been published on 4'-O-methylrobinetinidol 3'-O-beta-D-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215522D          

 33 36  0  0  1  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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
   -0.7145    2.0625    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
   -1.4289   -0.0000    0.0000 C   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
   -2.8579   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    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
   -4.2868    0.8250    0.0000 C   0  0  1  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
   -4.2868   -0.0000    0.0000 C   0  0  2  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
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   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
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 18 19  1  6  0  0  0
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 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
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   -0.0346   -4.4460    0.9638 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3397    2.0510   -1.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7317    1.3767    0.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5486    0.6745    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1559   -0.0636    1.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246   -0.1141    1.5803 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1087   -0.6529    2.7527 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7718   -0.4755    0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755   -0.8938    0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5029    0.0449   -0.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8571    0.0677   -0.3033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1925    0.7480   -1.4847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5224    0.6617   -1.8011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0721    1.9442   -2.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9573    3.0220   -1.5349 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3427   -3.3266    0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8973   -1.7603    0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6100    3.2667   -3.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0660    2.6328   -0.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3833    1.4075    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5390    0.4342    2.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5518   -1.0968    1.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2938    0.9477    1.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    0.0767    3.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9850    0.5588   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3122   -0.9156   -0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6117   -0.1063   -2.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1493    1.8020   -2.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5851    2.2020   -3.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879    3.4620   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6574   -1.4704   -1.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 32 23  1  0
 18  8  1  0
 16 10  1  0
  1 34  1  0
  1 35  1  0
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 20 48  1  0
 23 49  1  6
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 28 54  1  6
 29 55  1  0
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  8 39  1  6
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 13 41  1  0
 14 42  1  0
 15 43  1  0
 17 44  1  0
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 19 47  1  0
M  END


  Mrv1652309122215522D          

 33 36  0  0  1  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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
   -0.7145    2.0625    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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
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   -4.2868    0.8250    0.0000 C   0  0  1  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
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  4  6  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0329468

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O11/c1-30-21-13(26)5-10(20-12(25)4-9-2-3-11(24)7-14(9)31-20)6-15(21)32-22-19(29)18(28)17(27)16(8-23)33-22/h2-3,5-7,12,16-20,22-29H,4,8H2,1H3/t12-,16+,17+,18-,19+,20+,22+/m0/s1

> <INCHI_KEY>
SKDCNHZOXYIWDW-YOTCUMCBSA-N

> <FORMULA>
C22H26O11

> <MOLECULAR_WEIGHT>
466.439

> <EXACT_MASS>
466.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.03016498798375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{5-[(2R,3S)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.3270670220000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.037389794500184

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.435302628841473

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354949226

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
110.6264

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{5-[(2R,3S)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+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  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.336   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
4'-O-Methylrobinetinidol 3'-O-b-D-glucopyranoside	Generator
4'-O-Methylrobinetinidol 3'-O-β-D-glucopyranoside	Generator

Chemical Formula

C₂₂H₂₆O₁₁

Average Mass

466.4390 Da

Monoisotopic Mass

466.14751 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{5-[(2R,3S)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{5-[(2R,3S)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H26O11/c1-30-21-13(26)5-10(20-12(25)4-9-2-3-11(24)7-14(9)31-20)6-15(21)32-22-19(29)18(28)17(27)16(8-23)33-22/h2-3,5-7,12,16-20,22-29H,4,8H2,1H3/t12-,16+,17+,18-,19+,20+,22+/m0/s1

InChI Key

SKDCNHZOXYIWDW-YOTCUMCBSA-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

Species Name	Source	Reference
Acacia mearnsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid-3p-o-glycoside
Flavonoid o-glycoside
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Secondary alcohol
Oxacycle
Ether
Polyol
Acetal
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:68328 )
monosaccharide derivative (CHEBI:68328 )
catechin (CHEBI:68328 )
methoxyflavan (CHEBI:68328 )
flavan glycoside (CHEBI:68328 )

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	-0.33	ChemAxon
pKa (Strongest Acidic)	9.44	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.63 m³·mol⁻¹	ChemAxon
Polarizability	46.03 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

29368016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51041986

PDB ID

Not Available

ChEBI ID

68328

Good Scents ID

Not Available

References

General References

Kusano R, Ogawa S, Matsuo Y, Tanaka T, Yazaki Y, Kouno I: alpha-Amylase and lipase inhibitory activity and structural characterization of acacia bark proanthocyanidins. J Nat Prod. 2011 Feb 25;74(2):119-28. doi: 10.1021/np100372t. Epub 2010 Dec 30. [PubMed:21192716 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0329468)

MOL for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0329468 ((2s,3r,4s,5s,6r)-2-{5-[(2r,3s)-3,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-2-yl]-3-hydroxy-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)