NP-MRD: Showing NP-Card for (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0207602)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 04:16:45 UTC

Updated at

2022-09-05 04:16:45 UTC

NP-MRD ID

NP0207602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one

Description

Cernuoside 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. (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one is found in Ipomoea nil. (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one was first documented in 2012 (PMID: 22552843). Based on a literature review a small amount of articles have been published on Cernuoside (PMID: 28544207) (PMID: 25901916).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206162D          

 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
    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
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    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
    4.0668   -2.3479    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
    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
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 19 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
    0.3949   -1.6941   -1.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1597   -0.9381   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6207   -0.9998   -0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -1.8591   -1.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8344   -1.7215   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5804   -2.8878   -1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9640   -2.7603   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5834   -1.5346   -0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9629   -1.4680   -0.7629 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8303   -0.3748   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4255    0.8683   -0.9105 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4723   -0.5071   -1.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.0246    0.1589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9321    0.6887    0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690    1.7694    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728    2.3174    1.9542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7079    3.3869    2.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4818    1.7494    1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4748    0.6886    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5903    0.0923    0.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    0.4498    0.2852 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5431   -0.6766    0.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8467   -0.4075    1.2442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3444   -1.5746    2.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3116   -2.7265    1.3001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6507   -0.2416   -0.0281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0137   -0.1279    0.2273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0967    1.0335   -0.6783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8502    1.4209   -1.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6557    0.7411   -1.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0614    1.7921   -1.7164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7529    0.1567    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259   -2.6063   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1221   -3.8546   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5588   -3.6593   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4099   -0.5581   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9399    1.7353   -0.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    0.4094   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8052    2.1876    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7438    4.3502    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    2.1806    1.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    1.3240    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397    0.5378    1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773   -1.6704    3.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4252   -1.3518    2.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2697   -3.5608    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4095   -1.0665   -0.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4651   -1.0052    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0874    1.7884    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2628    1.8525   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5921   -0.1808   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2230    1.6223   -2.6835 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 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
 15 16  1  0
 16 17  1  0
 16 18  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
 21 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 23  1  0
 18 19  1  0
 12  5  1  0
 14 32  1  0
 25 46  1  0
 24 44  1  0
 24 45  1  0
 23 43  1  1
 21 42  1  1
 15 39  1  0
 17 40  1  0
 18 41  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
 30 51  1  6
 31 52  1  0
 28 49  1  1
 29 50  1  0
 26 47  1  6
 27 48  1  0
M  END


  Mrv1652309052206162D          

 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
    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
    3.3523   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    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
    4.0668   -2.3479    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
    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
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 19 32  2  0  0  0  0
 14 32  1  0  0  0  0
  2 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3C(=O)\C(OC3=CC(O)=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)31-13-6-9(23)5-12-16(13)17(26)14(30-12)4-8-1-2-10(24)11(25)3-8/h1-6,15,18-25,27-29H,7H2/b14-4-/t15-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
ZZERRGHHDDWLEN-YRDFTBLNSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.38

> <EXACT_MASS>
448.100561464

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.380453996299906

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
-0.28005506366666705

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.85777342845069

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.640268990613212

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923463095635

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
107.11430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.259  -7.463   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.259  -4.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.591  -2.843   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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   19   14    2                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3800 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3C(=O)\C(OC3=CC(O)=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)31-13-6-9(23)5-12-16(13)17(26)14(30-12)4-8-1-2-10(24)11(25)3-8/h1-6,15,18-25,27-29H,7H2/b14-4-/t15-,18-,19+,20-,21-/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.28	ChemAxon
pKa (Strongest Acidic)	7.64	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	43.38 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

C00008045

Chemspider ID

4952800

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6450182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee KJ, Song K, Song DY, Kim YS: Application of linear gradient elution in countercurrent chromatography for the separation of triterpenoid saponins from the roots of Pulsatilla koreana Nakai. J Sep Sci. 2017 Jul;40(13):2810-2818. doi: 10.1002/jssc.201700100. Epub 2017 Jun 19. [PubMed:28544207 ]
Jung HA, Park JJ, Min BS, Jung HJ, Islam MN, Choi JS: Inhibition of advanced glycation endproducts formation by Korean thistle, Cirsium maackii. Asian Pac J Trop Med. 2015 Jan;8(1):1-5. doi: 10.1016/S1995-7645(14)60178-4. [PubMed:25901916 ]
Gucluturk I, Detsi A, Weiss EK, Ioannou E, Roussis V, Kefalas P: Evaluation of anti-oxidant activity and identification of major polyphenolics of the invasive weed Oxalis pes-caprae. Phytochem Anal. 2012 Nov-Dec;23(6):642-6. doi: 10.1002/pca.2367. Epub 2012 May 3. [PubMed:22552843 ]
LOTUS database [Link]

Showing NP-Card for (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one (NP0207602)

MOL for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D MOL for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D SDF for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D-SDF for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

PDB for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D PDB for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

SMILES for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

INCHI for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

Structure for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)

3D Structure for NP0207602 ((2z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-benzofuran-3-one)