NP-MRD: Showing NP-Card for (2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0149650)

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Record Information

Version

2.0

Created at

2022-09-02 05:33:54 UTC

Updated at

2022-09-02 05:33:54 UTC

NP-MRD ID

NP0149650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Brandioside belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. (2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Brandisia hancei. (2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate was first documented in 2005 (PMID: 16142646). Based on a literature review a small amount of articles have been published on Brandioside (PMID: 25095374) (PMID: 24667350) (PMID: 24288293).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207332D          

 57 61  0  0  1  0            999 V2000
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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  1  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   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
 35 43  1  0  0  0  0
 43 44  1  6  0  0  0
 32 45  1  0  0  0  0
 45 46  1  0  0  0  0
  5 46  1  0  0  0  0
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 47 48  1  0  0  0  0
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 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 50 57  1  0  0  0  0
M  END

     RDKit          3D

105109  0  0  0  0  0  0  0  0999 V2000
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    3.0888   -1.1652    2.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8559   -2.1823    1.9380 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022207332D          

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  8  9  1  0  0  0  0
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 10 11  1  6  0  0  0
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 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 50 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@H](OC(C)=O)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C37H48O20/c1-15-26(44)28(46)30(48)35(52-15)51-14-24-32(56-25(43)9-6-18-4-7-20(39)22(41)12-18)33(57-36-31(49)29(47)27(45)16(2)53-36)34(54-17(3)38)37(55-24)50-11-10-19-5-8-21(40)23(42)13-19/h4-9,12-13,15-16,24,26-37,39-42,44-49H,10-11,14H2,1-3H3/b9-6+/t15-,16-,24+,26-,27-,28+,29+,30+,31+,32+,33-,34+,35+,36-,37+/m0/s1

> <INCHI_KEY>
RIHCCESRYIALPG-LQTIFAKJSA-N

> <FORMULA>
C37H48O20

> <MOLECULAR_WEIGHT>
812.771

> <EXACT_MASS>
812.273893946

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
80.33035974205436

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R,6R)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
0.5366250916666662

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.64312452718721

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.010185650038443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6764969324578356

> <JCHEM_POLAR_SURFACE_AREA>
310.28000000000003

> <JCHEM_REFRACTIVITY>
188.4242

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6R)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -5.390   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  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   46                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
CONECT   32   18   33   45                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   35   44                                                  
CONECT   44   43                                                            
CONECT   45   32   46                                                       
CONECT   46   45    5   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   57                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   50                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

View in JSmol

Synonyms

Value	Source
(beta-(3',4'-Dihydroxyphenyl)ethyl)-(2-O-acetyl)-(3,6-O-di-alpha-L-rhamnopyransoyl)-(4-O-caffeoyl)-beta-D-glucopyranoside	MeSH
2'-O-Acetylpoliumoside	MeSH

Chemical Formula

C₃₇H₄₈O₂₀

Average Mass

812.7710 Da

Monoisotopic Mass

812.27389 Da

IUPAC Name

(2R,3R,4S,5R,6R)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@H](OC(C)=O)[C@@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H]2OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C37H48O20/c1-15-26(44)28(46)30(48)35(52-15)51-14-24-32(56-25(43)9-6-18-4-7-20(39)22(41)12-18)33(57-36-31(49)29(47)27(45)16(2)53-36)34(54-17(3)38)37(55-24)50-11-10-19-5-8-21(40)23(42)13-19/h4-9,12-13,15-16,24,26-37,39-42,44-49H,10-11,14H2,1-3H3/b9-6+/t15-,16-,24+,26-,27-,28+,29+,30+,31+,32+,33-,34+,35+,36-,37+/m0/s1

InChI Key

RIHCCESRYIALPG-LQTIFAKJSA-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
Brandisia hancei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

Oligosaccharide
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Tyrosol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.69	ALOGPS
logP	0.54	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	310.28 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	188.42 m³·mol⁻¹	ChemAxon
Polarizability	80.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029848

Chemspider ID

9940594

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11765904

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu X, Li L, Yang YF, Huang CY, Huang GL: [Caffeoyl phenylethanoid glycosides from Callicarpa kwangtungensis]. Zhongguo Zhong Yao Za Zhi. 2014 May;39(9):1630-4. [PubMed:25095374 ]
Cai H, Xie Z, Liu G, Sun X, Peng G, Lin B, Liao Q: Isolation, identification and activities of natural antioxidants from Callicarpa kwangtungensis Chun. PLoS One. 2014 Mar 25;9(3):e93000. doi: 10.1371/journal.pone.0093000. eCollection 2014. [PubMed:24667350 ]
Yu SY, Lee IS, Jung SH, Lee YM, Lee YR, Kim JH, Sun H, Kim JS: Caffeoylated phenylpropanoid glycosides from Brandisia hancei inhibit advanced glycation end product formation and aldose reductase in vitro and vessel dilation in larval zebrafish in vivo. Planta Med. 2013 Dec;79(18):1705-9. doi: 10.1055/s-0033-1351101. Epub 2013 Nov 28. [PubMed:24288293 ]
Koo KA, Sung SH, Park JH, Kim SH, Lee KY, Kim YC: In vitro neuroprotective activities of phenylethanoid glycosides from Callicarpa dichotoma. Planta Med. 2005 Aug;71(8):778-80. doi: 10.1055/s-2005-871213. [PubMed:16142646 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0149650)

MOL for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0149650 ((2r,3r,4s,5r,6r)-5-(acetyloxy)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)