NP-MRD: Showing NP-Card for 1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (NP0321902)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 00:21:27 UTC

Updated at

2022-09-12 00:21:27 UTC

NP-MRD ID

NP0321902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

1-(2,3-Dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 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. 1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one is found in Bidens campylotheca and Bidens torta. 1-(2,3-Dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121517462D          

 33 35  0  0  0  0            999 V2000
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   10.1796   -1.2068   -1.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9124   -0.9467   -2.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8744   -0.5292   -1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0240   -0.3608   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0082    0.0478    0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078    0.3317    0.2362 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310    0.8599    1.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564    0.8244    1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.2009    0.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9205   -0.5096   -0.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0546    0.3226    0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2207   -0.3655   -0.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422   -0.3161   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    0.4059    0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1508    0.4889    0.8495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329   -0.1134    0.0648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9567    0.9064   -0.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0340    0.3970   -1.1420 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7690    1.6165   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1907    2.4232   -0.6333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9820   -0.3838   -0.2605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2368    0.1935   -0.2337 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3626   -0.4396    1.1208 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0811   -1.2821    1.9680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9735   -0.9905    1.0036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9684   -2.3028    0.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    1.0799    1.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5558    1.8252    2.6011 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4221    1.0384    1.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431    1.7603    2.4647 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    0.1621   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6365   -0.2622   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4396   -0.4183   -3.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0577   -2.0102   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9568   -1.4044   -2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4518   -0.2739   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0166   -0.5751    0.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1308    0.1775    1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881    1.4695    2.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0490    1.3933    2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -0.9469   -1.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7485   -0.8600   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557   -0.7350   -0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7304   -0.2157   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6507    1.3245   -2.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0705    2.2536   -2.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1578    2.5020   -0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0236   -1.4379   -0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8954   -0.5596   -0.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2822    0.5689    1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4368   -0.7681    2.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428   -1.0343    2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -2.6912    0.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535    1.8924    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727    2.2748    3.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730    0.4148   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5222   -0.2241   -3.7099 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  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  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 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
  6 31  1  0
 31 32  2  0
 32 33  1  0
 32  3  1  0
 29 11  1  0
 25 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  8 40  1  0
 12 41  1  0
 13 42  1  0
 16 43  1  6
 18 44  1  6
 19 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  6
 22 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  1
 26 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 33 57  1  0
M  END


  Mrv0541 04121517462D          

 33 35  0  0  0  0            999 V2000
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)C2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(O)=C2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24O11/c1-31-14-6-3-10(8-13(14)25)2-5-12(24)11-4-7-15(18(27)17(11)26)32-22-21(30)20(29)19(28)16(9-23)33-22/h2-8,16,19-23,25-30H,9H2,1H3

> <INCHI_KEY>
QUGFZLLBKBSAGW-UHFFFAOYSA-N

> <FORMULA>
C22H24O11

> <MOLECULAR_WEIGHT>
464.423

> <EXACT_MASS>
464.131861593

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.87350049179231

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.9003246633333332

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.828466484250596

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.325758308793513

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549420094

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
113.40820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.54e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670 -19.250   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -21.560   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.670 -25.410   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   11   30                                                  
CONECT   30   29                                                            
CONECT   31    6   32                                                       
CONECT   32   31    3   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄O₁₁

Average Mass

464.4230 Da

Monoisotopic Mass

464.13186 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)C2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(O)=C2O)C=C1O

InChI Identifier

InChI=1S/C22H24O11/c1-31-14-6-3-10(8-13(14)25)2-5-12(24)11-4-7-15(18(27)17(11)26)32-22-21(30)20(29)19(28)16(9-23)33-22/h2-8,16,19-23,25-30H,9H2,1H3

InChI Key

QUGFZLLBKBSAGW-UHFFFAOYSA-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
Bidens campylotheca	LOTUS Database	35616633
Bidens torta	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
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Linear 1,3-diarylpropanoid
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Alkyl glycoside
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Benzoyl
Catechol
Aryl ketone
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Monosaccharide
Fatty acyl
Oxane
Benzenoid
Acryloyl-group
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Secondary alcohol
Ketone
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen 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	0.58	ALOGPS
logP	0.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.33	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	7	ChemAxon
Refractivity	113.41 m³·mol⁻¹	ChemAxon
Polarizability	45.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74819211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one (NP0321902)

MOL for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

3D MOL for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

3D SDF for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

3D-SDF for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

PDB for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

3D PDB for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

SMILES for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

INCHI for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

Structure for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)

3D Structure for NP0321902 (1-(2,3-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one)