NP-MRD: Showing NP-Card for bracteoside (NP0252264)

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Record Information

Version

2.0

Created at

2022-09-07 15:43:17 UTC

Updated at

2022-09-07 15:43:17 UTC

NP-MRD ID

NP0252264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bracteoside

Description

Bracteoside belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. bracteoside is found in Centaurea bracteata. bracteoside was first documented in 2022 (PMID: 35533533). Based on a literature review very few articles have been published on Bracteoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217432D          

 34 37  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  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   -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
   -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
   -1.4289    0.8250    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
   -0.7145    1.2375    0.0000 C   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
    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
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.8579   -2.4750    0.0000 O   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
    1.4289   -2.4750    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    5.1810    1.8050   -2.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7433    2.0194   -1.3508 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828    1.3886   -0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199    0.1799   -0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8356   -0.5762    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1071   -0.1153   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266   -0.9187    0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0805   -2.2372    0.5082 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1944   -3.0364    0.7498 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7986   -2.7306    0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155   -1.9196    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536   -0.3563    0.1210 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    0.1731   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1157   -0.4114    0.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1088    0.1912    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451   -0.4481    0.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5576   -0.0166    0.5318 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0643    0.1089    1.8189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4257    0.1841    1.8871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0249   -1.0620    2.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2699   -1.1529    2.6204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356   -2.1225    2.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1174    0.5374    0.6201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0077    1.9267    0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7136   -0.2573   -0.5684 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7120   -1.0994   -1.0538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4288   -0.9932   -0.2728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7792   -1.1864   -1.5064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1474    1.3988   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0087    2.0473   -0.8885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    3.2774   -1.5207 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2230    1.4160   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601    2.0411   -1.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    3.1472   -1.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911    0.8321   -3.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8608    2.6401   -3.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2858    1.8116   -2.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3161    0.8866   -0.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2333   -0.5369    0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5702   -3.5426   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6495   -3.7496    0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7196   -2.3231    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600   -1.3764    0.8739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125    0.9622    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6741    0.9937    2.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -2.0553    2.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2199    0.3594    0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8889    2.3566    1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4772    0.4715   -1.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -0.5443   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5656   -1.9446    0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -2.1282   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625    1.9015   -0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883    3.7832   -1.7019 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 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 15 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 33  3  1  0
 11  5  1  0
 32 13  1  0
 27 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 14 43  1  0
 17 44  1  6
 19 45  1  1
 23 47  1  1
 24 48  1  0
 25 49  1  6
 26 50  1  0
 27 51  1  1
 28 52  1  0
 22 46  1  0
 29 53  1  0
 31 54  1  0
  6 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
M  END


  Mrv1652309072217432D          

 34 37  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  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   -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
   -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
   -1.4289    0.8250    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
   -0.7145    1.2375    0.0000 C   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
    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
    5.0013   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    2.8579   -2.4750    0.0000 O   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
    1.4289   -2.4750    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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0252264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC(O[C@@H]3OC([C@@H](O)[C@H](O)C3O)C(O)=O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O12/c1-31-19-14(25)13-11(24)6-10(7-12(13)33-18(19)8-2-4-9(23)5-3-8)32-22-17(28)15(26)16(27)20(34-22)21(29)30/h2-7,15-17,20,22-24,26-28H,1H3,(H,29,30)/t15-,16-,17?,20?,22+/m0/s1

> <INCHI_KEY>
DKWQRYDJKSHULB-XHOQVIGFSA-N

> <FORMULA>
C22H20O12

> <MOLECULAR_WEIGHT>
476.39

> <EXACT_MASS>
476.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.10077895118511

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_LOGP>
0.6248986196666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.088879716527909

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.719942395115593

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778068572

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
111.6443

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
bracteoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   17   28                                                  
CONECT   28   27                                                            
CONECT   29   15   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   13   33                                                  
CONECT   33   32    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₂

Average Mass

476.3900 Da

Monoisotopic Mass

476.09548 Da

IUPAC Name

(3S,4S,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

bracteoside

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC(O[C@@H]3OC([C@@H](O)[C@H](O)C3O)C(O)=O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H20O12/c1-31-19-14(25)13-11(24)6-10(7-12(13)33-18(19)8-2-4-9(23)5-3-8)32-22-17(28)15(26)16(27)20(34-22)21(29)30/h2-7,15-17,20,22-24,26-28H,1H3,(H,29,30)/t15-,16-,17?,20?,22+/m0/s1

InChI Key

DKWQRYDJKSHULB-XHOQVIGFSA-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
Centaurea bracteata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
3-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
3-methoxychromone
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Monosaccharide
Pyran
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112673 )

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	0.62	ChemAxon
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.64 m³·mol⁻¹	ChemAxon
Polarizability	45.1 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

C00013809

Chemspider ID

24845338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44259644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Avula B, Katragunta K, Wang YH, Ali Z, Khan IA: Simultaneous determination and characterization of flavonoids, sesquiterpene lactone, and other phenolics from Centaurea benedicta and dietary supplements using UHPLC-PDA-MS and LC-DAD-QToF. J Pharm Biomed Anal. 2022 Jul 15;216:114806. doi: 10.1016/j.jpba.2022.114806. Epub 2022 May 4. [PubMed:35533533 ]
LOTUS database [Link]

Showing NP-Card for bracteoside (NP0252264)

MOL for NP0252264 (bracteoside)

3D MOL for NP0252264 (bracteoside)

3D SDF for NP0252264 (bracteoside)

3D-SDF for NP0252264 (bracteoside)

PDB for NP0252264 (bracteoside)

3D PDB for NP0252264 (bracteoside)

SMILES for NP0252264 (bracteoside)

INCHI for NP0252264 (bracteoside)

Structure for NP0252264 (bracteoside)

3D Structure for NP0252264 (bracteoside)