NP-MRD: Showing NP-Card for (2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one (NP0324156)

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Record Information

Version

2.0

Created at

2022-09-12 04:03:08 UTC

Updated at

2022-09-12 04:03:08 UTC

NP-MRD ID

NP0324156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

Description

Coreopsin belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. (2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one is found in Abies pindrow, Bahiopsis laciniata, Butea monosperma, Calanticaria greggii, Cosmos sulphureus, Helianthus carnosus, Lasthenia californica and Wedelia prostrata. (2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one was first documented in 2016 (PMID: 27291468). Based on a literature review a small amount of articles have been published on coreopsin (PMID: 32045684) (PMID: 26521095).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206032D          

 31 33  0  0  1  0            999 V2000
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   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
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    4.2381    0.7610    0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000    0.5443   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3961    0.6557   -1.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926    0.9662   -2.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7999    1.0817   -3.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8331    0.8896   -4.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1062    1.0247   -5.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3453    1.3543   -6.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6405    1.4939   -7.7074 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3323    1.5504   -5.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6169    1.8892   -5.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0776    1.4202   -4.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    0.2235    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0083    0.1774    1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718   -0.1203    2.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.3797    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272   -0.6677    2.5470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7166   -0.9991    2.1301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4681    0.1676    2.2539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8347   -0.0877    2.2109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5453    1.1778    1.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0758    1.5974    0.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1694   -0.6809    3.5479 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5350   -0.8438    3.7458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5218   -2.0528    3.5827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4758   -2.4996    4.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2056   -2.1421    2.9253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2161   -3.2680    2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531   -0.3377    0.4592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175   -0.0309   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -0.0053   -1.6193 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140    0.5000   -2.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    1.1332   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8259    0.6282   -4.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079    0.8626   -6.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8582    1.3389   -8.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3499    2.0363   -5.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8469    1.5726   -3.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9168    0.3743    2.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416   -0.1685    3.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6859   -1.2134    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0700   -0.8497    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6413    1.0666    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2674    2.0049    2.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    0.7748    0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7020   -0.0448    4.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9694   -1.3823    3.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695   -2.7165    3.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983   -1.9022    5.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4548   -2.4396    3.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192   -3.6840    2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612   -0.5324   -0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394   -0.2182   -2.1066 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 15  2  0
 15 14  1  0
 14 13  2  0
 13  2  1  0
  2  1  2  0
  2  3  1  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
 13 30  1  0
 30 31  1  0
 30 29  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
 29 16  1  0
 12  5  1  0
 22 45  1  0
 21 43  1  0
 21 44  1  0
 20 42  1  6
 18 41  1  6
 15 40  1  0
 14 39  1  0
  3 32  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
 31 53  1  0
 29 52  1  0
 27 50  1  1
 28 51  1  0
 25 48  1  6
 26 49  1  0
 23 46  1  1
 24 47  1  0
M  END


  Mrv1652309122206032D          

 31 33  0  0  1  0            999 V2000
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   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
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  1  0  0  0  0
 29 30  2  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C(C(=O)\C=C\C3=CC=C(O)C(O)=C3)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O10/c22-9-17-18(27)19(28)20(29)21(31-17)30-11-3-4-12(15(25)8-11)13(23)5-1-10-2-6-14(24)16(26)7-10/h1-8,17-22,24-29H,9H2/b5-1+/t17-,18-,19+,20-,21-/m1/s1

> <INCHI_KEY>
QMVODIKHHIRSGI-RWGOFXMDSA-N

> <FORMULA>
C21H22O10

> <MOLECULAR_WEIGHT>
434.397

> <EXACT_MASS>
434.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.907773076562286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

> <JCHEM_LOGP>
1.0579959289999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.005546403980741

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.047710651936507

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225725

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
106.94500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.670   6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.338   6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.672   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.005   6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.005   8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.005   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      17.338   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.670   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
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    2   14   30                                                  
CONECT   14   13   15                                                       
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   13   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂O₁₀

Average Mass

434.3970 Da

Monoisotopic Mass

434.12130 Da

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

Traditional Name

(2E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C(C(=O)\C=C\C3=CC=C(O)C(O)=C3)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H22O10/c22-9-17-18(27)19(28)20(29)21(31-17)30-11-3-4-12(15(25)8-11)13(23)5-1-10-2-6-14(24)16(26)7-10/h1-8,17-22,24-29H,9H2/b5-1+/t17-,18-,19+,20-,21-/m1/s1

InChI Key

QMVODIKHHIRSGI-RWGOFXMDSA-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
Abies pindrow	LOTUS Database	35616633
Bahiopsis laciniata	LOTUS Database	35616633
Butea monosperma	LOTUS Database	35616633
Calanticaria greggii	LOTUS Database	35616633
Cosmos sulphureus	LOTUS Database	35616633
Helianthus carnosus	LOTUS Database	35616633
Lasthenia californica	LOTUS Database	35616633
Wedelia prostrata	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Linear 1,3-diarylpropanoid
Cinnamylphenol
Alkyl glycoside
Cinnamic acid or derivatives
Hexose monosaccharide
Hydroxycinnamic acid or derivatives
Glycosyl compound
O-glycosyl compound
Phenoxy compound
Benzoyl
Catechol
Phenol ether
Styrene
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Alpha,beta-unsaturated ketone
Vinylogous acid
Acryloyl-group
Enone
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Aldehyde
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.06	ChemAxon
pKa (Strongest Acidic)	7.05	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.94 m³·mol⁻¹	ChemAxon
Polarizability	42.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00007218

Chemspider ID

58837424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12303943

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li Y, Huang C, Fu W, Zhang H, Lao Y, Zhou H, Tan H, Xu H: Screening of the active fractions from the Coreopsis tinctoria Nutt. Flower on diabetic endothelial protection and determination of the underlying mechanism. J Ethnopharmacol. 2020 May 10;253:112645. doi: 10.1016/j.jep.2020.112645. Epub 2020 Feb 8. [PubMed:32045684 ]
Lam SC, Liu X, Chen XQ, Hu DJ, Zhao J, Long ZR, Fan B, Li SP: Chemical characteristics of different parts of Coreopsis tinctoria in China using microwave-assisted extraction and high-performance liquid chromatography followed by chemometric analysis. J Sep Sci. 2016 Aug;39(15):2919-27. doi: 10.1002/jssc.201600365. [PubMed:27291468 ]
Chen LX, Hu DJ, Lam SC, Ge L, Wu D, Zhao J, Long ZR, Yang WJ, Fan B, Li SP: Comparison of antioxidant activities of different parts from snow chrysanthemum (Coreopsis tinctoria Nutt.) and identification of their natural antioxidants using high performance liquid chromatography coupled with diode array detection and mass spectrometry and 2,2'-azinobis(3-ethylbenzthiazoline-sulfonic acid)diammonium salt-based assay. J Chromatogr A. 2016 Jan 8;1428:134-42. doi: 10.1016/j.chroma.2015.10.037. Epub 2015 Oct 19. [PubMed:26521095 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one (NP0324156)

MOL for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

3D MOL for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

3D SDF for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

3D-SDF for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

PDB for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

3D PDB for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

SMILES for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

INCHI for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

Structure for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)

3D Structure for NP0324156 ((2e)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-one)