NP-MRD: Showing NP-Card for 4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid (NP0256029)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-07 20:44:08 UTC

Updated at

2022-09-07 20:44:08 UTC

NP-MRD ID

NP0256029

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid

Description

Dracunculifoside B belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid is found in Baccharis dracunculifolia. It was first documented in 2002 (PMID: 35412727). Based on a literature review a significant number of articles have been published on Dracunculifoside B (PMID: 36099392) (PMID: 31661213) (PMID: 31593386) (PMID: 29589881).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222442D          

 34 36  0  0  1  0            999 V2000
    8.5737   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   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
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   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
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   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
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    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
    7.1447    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  2  0  0  0  0  0  0  0  0  0
    4.2868    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  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -0.7001    0.4539    1.2486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7190    0.8581    0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0144    0.3053    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1476    0.6621    0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4631    0.1511    0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5598    0.6172    0.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8390    0.2246    0.3614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0673   -0.7030    1.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3831   -1.1295    1.6195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0089   -1.1939    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2114   -2.1320    3.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -0.7696    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618    1.7742   -0.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661    2.3485   -0.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6418    1.4232   -1.3791 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1300    0.4416   -0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    0.0162   -1.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9460   -0.8642   -0.2724 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -0.9094    0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3690   -2.0163    1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5348   -2.1151    1.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5091   -1.1447    1.8993 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7391   -1.2678    2.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072   -0.3644    2.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9946   -2.3526    3.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2694   -0.0575    1.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0786    0.0488    0.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9098    1.1699   -0.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0891   -0.7099   -2.4491 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9643   -0.3060   -3.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6893   -0.5169   -2.9357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1824   -1.5156   -2.4706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1205    0.8388   -2.6749 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3475    1.7538   -3.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0675   -0.4185    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0445    1.3928   -0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4043    1.3557   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6615    0.6269   -0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1666   -0.7769    1.1021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1373   -2.4463    3.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8778   -1.1545    2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6737    3.0394   -1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056    3.0058   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5261    2.0667   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8924    0.9296   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -2.7946    1.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7504   -2.9757    2.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -2.7173    4.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0187    0.7342    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828    1.9127   -0.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -1.8178   -2.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4107    0.5411   -3.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7056   -0.6530   -4.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2401   -2.3899   -2.4028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9888    0.7113   -2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1996    1.5624   -4.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 15  1  0
 15 14  1  0
 14 13  1  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
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 26  1  0
 26 27  2  0
 27 28  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 12  5  1  0
 27 19  1  0
 34 56  1  0
 33 55  1  1
 15 44  1  6
 14 42  1  0
 14 43  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 17 45  1  6
 20 46  1  0
 21 47  1  0
 26 49  1  0
 28 50  1  0
 25 48  1  0
 29 51  1  1
 30 52  1  0
 31 53  1  6
 32 54  1  0
M  END


  Mrv1652309072222442D          

 34 36  0  0  1  0            999 V2000
    8.5737   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   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
    7.8592   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   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
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 O   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
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    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
    7.1447    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  2  0  0  0  0  0  0  0  0  0
    4.2868    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  1  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0256029

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=CC=C(C=C2O)C(O)=O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O12/c23-12-4-1-10(7-13(12)24)2-6-17(26)32-9-16-18(27)19(28)20(29)22(34-16)33-15-5-3-11(21(30)31)8-14(15)25/h1-8,16,18-20,22-25,27-29H,9H2,(H,30,31)/b6-2+/t16-,18-,19+,20-,22-/m1/s1

> <INCHI_KEY>
UHEUVGKZEYAYTJ-ICBACFOWSA-N

> <FORMULA>
C22H22O12

> <MOLECULAR_WEIGHT>
478.406

> <EXACT_MASS>
478.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
45.18544882174319

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid

> <JCHEM_LOGP>
1.1823900619999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.110183034223606

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.102104884859992

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491103097336124

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
112.9499

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      16.004  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004  10.780   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.338   8.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669  -0.000   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                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   29                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27                                                            
CONECT   29   17   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   15   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₂O₁₂

Average Mass

478.4060 Da

Monoisotopic Mass

478.11113 Da

IUPAC Name

4-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid

Traditional Name

4-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)O[C@@H](OC2=CC=C(C=C2O)C(O)=O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H22O12/c23-12-4-1-10(7-13(12)24)2-6-17(26)32-9-16-18(27)19(28)20(29)22(34-16)33-15-5-3-11(21(30)31)8-14(15)25/h1-8,16,18-20,22-25,27-29H,9H2,(H,30,31)/b6-2+/t16-,18-,19+,20-,22-/m1/s1

InChI Key

UHEUVGKZEYAYTJ-ICBACFOWSA-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
Baccharis dracunculifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Phenol ether
Styrene
Phenoxy compound
Benzoyl
Catechol
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Polyol
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	1.18	ChemAxon
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.95 m³·mol⁻¹	ChemAxon
Polarizability	45.19 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

C00032915

Chemspider ID

9180502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11005311

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
Authors unspecified: Cognitive Impairment in Adults with Non-Central Nervous System Cancers (PDQ(R)): Patient Version. 2002. [PubMed:29589881 ]
LOTUS database [Link]

Showing NP-Card for 4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid (NP0256029)

MOL for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

3D MOL for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

3D SDF for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

3D-SDF for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

PDB for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

3D PDB for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

SMILES for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

INCHI for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

Structure for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)

3D Structure for NP0256029 (4-{[(2s,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxybenzoic acid)