NP-MRD: Showing NP-Card for aureusidin 6-o-glucoside (NP0228304)

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Record Information

Version

2.0

Created at

2022-09-06 07:54:18 UTC

Updated at

2022-09-06 07:54:18 UTC

NP-MRD ID

NP0228304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aureusidin 6-o-glucoside

Description

Aureusidin 6-O-beta-glucoside belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton. Aureusidin 6-O-beta-glucoside is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. aureusidin 6-o-glucoside is found in Antirrhinum majus, Helichrysum arenarium and Zinnia elegans. aureusidin 6-o-glucoside was first documented in 2006 (PMID: 16832053). Based on a literature review very few articles have been published on aureusidin 6-O-beta-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209542D          

 32 35  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9246    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  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  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 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
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 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
 14 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    3.3412    2.9533   -3.2446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8176    2.1944   -2.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5672    1.3795   -1.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8623    1.2741   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4266    0.3900   -0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5306    0.7471    0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0840   -0.0770    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5555   -1.3209    1.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870   -2.1922    2.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4440   -1.7145    0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8728   -2.9418    1.1517 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8898   -0.8668   -0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340    0.7010   -0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3395    1.0339   -1.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0753    0.6682   -0.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799    1.1637   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463    0.8499   -0.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -0.0075    0.1629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6598   -0.9581   -0.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3240   -1.6447    0.5912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8415   -2.9979    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4764   -3.5555    1.2599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5092   -0.8560    1.1281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7802   -1.1722    2.4570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1058    0.5957    1.0653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4793    1.1903   -0.1365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    0.7136    1.2412 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1869    0.2215    2.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9500    2.0800   -2.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2840    2.4662   -2.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3956    3.3713   -3.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4106    1.9534   -2.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4847    1.8643   -1.9918 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9659    1.7212    0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9661    0.2159    1.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8895   -1.9619    3.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650   -3.6363    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -1.1660   -0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0093   -0.0471    0.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5512    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155   -1.8226    1.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6007   -2.9327   -0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048   -3.6566   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4424   -3.3303    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3721   -1.0112    0.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3169   -0.5018    2.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5657    1.1674    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7044    1.1943   -0.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3829    1.8004    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432    0.8440    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330    2.5041   -2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2977    3.6640   -4.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
  2  1  2  0
  2  3  1  0
  3 13  1  0
 13 14  1  0
 14 15  2  0
  3  4  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  1  0
 10 12  2  0
 18 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 20  1  0
 15 16  1  0
 12  5  1  0
 14 32  1  0
 22 44  1  0
 21 42  1  0
 21 43  1  0
 20 41  1  1
 18 40  1  1
 29 51  1  0
 31 52  1  0
 15 39  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 27 49  1  1
 28 50  1  0
 25 47  1  1
 26 48  1  0
 23 45  1  6
 24 46  1  0
M  END


  Mrv1652309062209542D          

 32 35  0  0  1  0            999 V2000
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    1.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9246    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9246   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  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  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 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
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 16 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
 14 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)\C(OC3=C2)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-7-15-18(27)19(28)20(29)21(32-15)30-9-5-12(25)16-13(6-9)31-14(17(16)26)4-8-1-2-10(23)11(24)3-8/h1-6,15,18-25,27-29H,7H2/b14-4-/t15-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
AMJCTDBATIKENQ-YRDFTBLNSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.52426461547894

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

> <JCHEM_LOGP>
0.369944936333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.950854323171335

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.217211514276737

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343758667

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.1143

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
aureusidin 6-O-glucoside

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.630   0.031   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.400   1.365   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.630   2.698   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.400   4.032   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.090   2.698   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.320   4.032   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.320   1.365   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259   0.237   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.592  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.926   0.237   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.926   1.777   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.592  -2.073   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.926  -2.843   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   14    2                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
2-((3,4-Dihydroxyphenyl)methylene)-6-(beta-D-glucopyranosyloxy)-4-hydroxy-3(2H)-benzofuranone	ChEBI
Aureusidin 6-O-beta-D-glucoside	ChEBI
2-((3,4-Dihydroxyphenyl)methylene)-6-(b-D-glucopyranosyloxy)-4-hydroxy-3(2H)-benzofuranone	Generator
2-((3,4-Dihydroxyphenyl)methylene)-6-(β-D-glucopyranosyloxy)-4-hydroxy-3(2H)-benzofuranone	Generator
Aureusidin 6-O-b-D-glucoside	Generator
Aureusidin 6-O-β-D-glucoside	Generator
Aureusidin 6-O-b-glucoside	Generator
Aureusidin 6-O-β-glucoside	Generator

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

(2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzofuran-3-one

Traditional Name

aureusidin 6-O-glucoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)\C(OC3=C2)=C\C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H20O11/c22-7-15-18(27)19(28)20(29)21(32-15)30-9-5-12(25)16-13(6-9)31-14(17(16)26)4-8-1-2-10(23)11(24)3-8/h1-6,15,18-25,27-29H,7H2/b14-4-/t15-,18-,19+,20-,21-/m1/s1

InChI Key

AMJCTDBATIKENQ-YRDFTBLNSA-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
Antirrhinum majus	LOTUS Database	35616633
Helichrysum arenarium	LOTUS Database	35616633
Zinnia elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aurone o-glycosides. These are aurone flavonoids containing a carbohydrate moiety O-glycosidically bound to the aurone skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Aurone O-glycosides

Alternative Parents

Substituents

Aurone-6-o-glycoside
Aurone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzofuran
Coumaran
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:66905 )
hydroxyaurone (CHEBI:66905 )
aurones (C16409 )

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	0.37	ChemAxon
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.11 m³·mol⁻¹	ChemAxon
Polarizability	43.52 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

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321164

PDB ID

Not Available

ChEBI ID

66905

Good Scents ID

Not Available

References

General References

Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, Yamaguchi M, Nakayama T, Tanaka T, Kusumi T, Tanaka Y: Yellow flowers generated by expression of the aurone biosynthetic pathway. Proc Natl Acad Sci U S A. 2006 Jul 18;103(29):11075-80. doi: 10.1073/pnas.0604246103. Epub 2006 Jul 10. [PubMed:16832053 ]
LOTUS database [Link]

Showing NP-Card for aureusidin 6-o-glucoside (NP0228304)

MOL for NP0228304 (aureusidin 6-o-glucoside)

3D MOL for NP0228304 (aureusidin 6-o-glucoside)

3D SDF for NP0228304 (aureusidin 6-o-glucoside)

3D-SDF for NP0228304 (aureusidin 6-o-glucoside)

PDB for NP0228304 (aureusidin 6-o-glucoside)

3D PDB for NP0228304 (aureusidin 6-o-glucoside)

SMILES for NP0228304 (aureusidin 6-o-glucoside)

INCHI for NP0228304 (aureusidin 6-o-glucoside)

Structure for NP0228304 (aureusidin 6-o-glucoside)

3D Structure for NP0228304 (aureusidin 6-o-glucoside)