NP-MRD: Showing NP-Card for apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside (NP0042161)

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Record Information

Version

2.0

Created at

2021-06-20 23:53:39 UTC

Updated at

2021-06-30 00:17:05 UTC

NP-MRD ID

NP0042161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside

Provided By

JEOL Database JEOL Logo

Description

Echinacin belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside is found in Cucumis sativus , Echinop echinatus, Echinops echinatus, Lagopsis supina, Leucas aspera, Leucas cephalotes, Leucas neufliseana, Marrubium vulgare, Phlomis floccosa, Pogostemon cablin , Populus tremuloides, Dasiphora fruticosa, Scolopia chinensis, Sideritis syriaca, Stachys aegyptiaca, Stachys alopecuros (L.) Benth., Stachys anisochila Vis.et Panc., Stachys bombycina, Stachys byzantina, Stachys germanica L. , Stachys lanata, Stachys ocymastrum, Stachys officinalis (L.) Trev. , Stachys palustris L. , Stachys plumosa Griseb., Stachys scardica Griseb., Stachys sylvatica L., Tinospora crispa and Turnera diffusa . apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside was first documented in 2005 (PMID: 15856390). Based on a literature review a small amount of articles have been published on Echinacin (PMID: 18948180) (PMID: 17597571).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101533D          

 68 72  0  0  0  0            999 V2000
    3.1397   -2.0198    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.9454    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648    0.2553   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    0.1809   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    1.2998   -2.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    2.6285   -2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    3.6669   -3.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    3.3730   -4.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716    4.3568   -5.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    2.0606   -4.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089    1.0248   -3.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.6322    1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -1.7440    2.4349 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    3.1397   -2.0198    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.9454    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
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 19 54  1  0
 28 57  1  0
 29 58  1  0
 32 60  1  0
 33 61  1  0
 31 59  1  0
 21 55  1  0
M  END


  Mrv1652306212101533D          

 68 72  0  0  0  0            999 V2000
    3.1397   -2.0198    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.9454    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648    0.2553   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    0.1809   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    1.2998   -2.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    2.6285   -2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    3.6669   -3.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    3.3730   -4.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716    4.3568   -5.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    2.0606   -4.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089    1.0248   -3.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.6322    1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -1.7440    2.4349 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1998   -2.1958    2.1973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0302   -2.4935    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3102   -2.8425    0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4354   -3.1090   -0.9399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -2.0747   -1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369   -2.4475   -3.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -1.4907   -4.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505   -1.9346   -5.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579   -0.1486   -3.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5209    0.8913   -4.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4436    0.6143   -5.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862    2.2719   -4.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    2.5190   -2.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455    3.8832   -2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2086    4.0638   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    5.3414   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    6.4513   -1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221    7.6785   -0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151    6.3053   -2.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    5.0245   -3.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    1.5346   -2.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    0.2306   -2.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -0.7291   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074   -4.1347    1.2025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0706   -4.5059    0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5474   -3.9229    2.7078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7939   -5.1480    3.4156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -3.4241    3.0497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -3.1113    4.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140    1.1549   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -0.7625   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    2.8751   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    4.6886   -2.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309    5.2073   -4.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    1.8408   -5.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9832    0.0026   -4.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -1.3919    3.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3525   -2.5703    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -1.3519    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -2.0426    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -3.4910   -3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815   -1.1600   -6.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    3.0243   -5.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    3.2081   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    5.4669    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    8.3512   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    7.1660   -3.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277    4.9345   -4.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -0.3929   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -4.9763    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494   -4.5656   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -3.2150    3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -5.5038    3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -4.2297    2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549   -3.8938    4.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
 41 42  1  0  0  0  0
 39 40  1  0  0  0  0
 37 38  1  0  0  0  0
 11  5  1  0  0  0  0
  2  1  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 35 34  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 34  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 22 35  1  0  0  0  0
  5  4  1  0  0  0  0
 35 36  2  0  0  0  0
 36 18  1  0  0  0  0
  4  3  2  0  0  0  0
 18 19  2  0  0  0  0
 10 11  2  0  0  0  0
 19 20  1  0  0  0  0
 20 22  2  0  0  0  0
  3  2  1  0  0  0  0
  7  8  2  0  0  0  0
 27 28  2  0  0  0  0
  2 12  1  0  0  0  0
 28 29  1  0  0  0  0
 16 37  1  0  0  0  0
 29 30  2  0  0  0  0
 37 39  1  0  0  0  0
 30 32  1  0  0  0  0
 39 41  1  0  0  0  0
 32 33  2  0  0  0  0
 33 27  1  0  0  0  0
 27 26  1  0  0  0  0
 41 14  1  0  0  0  0
 30 31  1  0  0  0  0
 14 15  1  0  0  0  0
 23 24  2  0  0  0  0
 18 17  1  0  0  0  0
 15 16  1  0  0  0  0
 20 21  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 16 17  1  0  0  0  0
  6 45  1  0  0  0  0
  7 46  1  0  0  0  0
 10 48  1  0  0  0  0
 11 49  1  0  0  0  0
  9 47  1  0  0  0  0
  4 44  1  0  0  0  0
  3 43  1  0  0  0  0
 16 53  1  1  0  0  0
 41 67  1  1  0  0  0
 42 68  1  0  0  0  0
 39 65  1  1  0  0  0
 40 66  1  0  0  0  0
 37 63  1  6  0  0  0
 38 64  1  0  0  0  0
 13 50  1  0  0  0  0
 13 51  1  0  0  0  0
 14 52  1  1  0  0  0
 25 56  1  0  0  0  0
 36 62  1  0  0  0  0
 19 54  1  0  0  0  0
 28 57  1  0  0  0  0
 29 58  1  0  0  0  0
 32 60  1  0  0  0  0
 33 61  1  0  0  0  0
 31 59  1  0  0  0  0
 21 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(OC3=C([H])C(O[H])=C4C(=O)C([H])=C(OC4=C3[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
WPQRDUGBKUNFJW-ZZSHFKPLSA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.45439811897489

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.168946436666666

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.65836016029198

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.294211715705087

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491102896195384

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
146.6069

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    3.1397   -2.0198    0.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6363   -0.9454    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648    0.2553   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1961    0.1809   -1.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    1.2998   -2.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    2.6285   -2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    3.6669   -3.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2797    3.3730   -4.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716    4.3568   -5.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    2.0606   -4.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089    1.0248   -3.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -0.6322    1.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6486   -1.7440    2.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1998   -2.1958    2.1973 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0302   -2.4935    0.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3102   -2.8425    0.4647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4354   -3.1090   -0.9399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2047   -2.0747   -1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1369   -2.4475   -3.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -1.4907   -4.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505   -1.9346   -5.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579   -0.1486   -3.7894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5209    0.8913   -4.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4436    0.6143   -5.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3862    2.2719   -4.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    2.5190   -2.9961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455    3.8832   -2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2086    4.0638   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    5.3414   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    6.4513   -1.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1221    7.6785   -0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6151    6.3053   -2.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7656    5.0245   -3.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    1.5346   -2.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    0.2306   -2.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -0.7291   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074   -4.1347    1.2025 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0706   -4.5059    0.9403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5474   -3.9229    2.7078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7939   -5.1480    3.4156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1408   -3.4241    3.0497 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0797   -3.1113    4.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2140    1.1549   -0.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -0.7625   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5456    2.8751   -1.1430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5545    4.6886   -2.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4309    5.2073   -4.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    1.8408   -5.9662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9832    0.0026   -4.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776   -1.3919    3.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3525   -2.5703    2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4569   -1.3519    2.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0115   -2.0426    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -3.4910   -3.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6815   -1.1600   -6.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    3.0243   -5.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    3.2081   -0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996    5.4669    0.3708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    8.3512   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    7.1660   -3.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2277    4.9345   -4.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -0.3929   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -4.9763    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1494   -4.5656   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -3.2150    3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215   -5.5038    3.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -4.2297    2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549   -3.8938    4.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
 41 42  1  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       3.140  -2.020   0.157  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.636  -0.945   0.439  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.665   0.255  -0.421  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.196   0.181  -1.651  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.229   1.300  -2.601  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.412   2.628  -2.193  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.430   3.667  -3.130  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.280   3.373  -4.479  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.272   4.357  -5.423  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.129   2.061  -4.908  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.109   1.025  -3.970  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.944  -0.632   1.565  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.649  -1.744   2.435  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.200  -2.196   2.197  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.030  -2.494   0.804  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.310  -2.842   0.465  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.435  -3.109  -0.940  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.205  -2.075  -1.807  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.137  -2.447  -3.153  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.910  -1.491  -4.140  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.851  -1.935  -5.433  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.758  -0.149  -3.789  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.521   0.891  -4.795  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.444   0.614  -5.987  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.386   2.272  -4.311  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.492   2.519  -2.996  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.346   3.883  -2.438  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.209   4.064  -1.160  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.363   5.341  -0.616  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.047   6.451  -1.341  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.122   7.678  -0.774  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.615   6.305  -2.600  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.766   5.024  -3.143  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.711   1.535  -2.041  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.835   0.231  -2.454  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.053  -0.729  -1.460  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.707  -4.135   1.202  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.071  -4.506   0.940  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.547  -3.923   2.708  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.794  -5.148   3.416  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.141  -3.424   3.050  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.080  -3.111   4.442  0.00  0.00           O+0
HETATM   43  H   UNK     0       2.214   1.155  -0.025  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.604  -0.763  -2.012  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.546   2.875  -1.143  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.555   4.689  -2.785  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.431   5.207  -4.981  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.018   1.841  -5.966  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.983   0.003  -4.322  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.778  -1.392   3.464  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.353  -2.570   2.283  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.457  -1.352   2.448  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.011  -2.043   0.740  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.251  -3.491  -3.436  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.682  -1.160  -6.016  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.176   3.024  -5.059  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.538   3.208  -0.576  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.800   5.467   0.371  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.254   8.351  -1.365  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.948   7.166  -3.171  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.228   4.934  -4.124  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.096  -0.393  -0.430  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.085  -4.976   0.874  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.149  -4.566  -0.033  0.00  0.00           H+0
HETATM   65  H   UNK     0      -2.300  -3.215   3.077  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.622  -5.504   3.032  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.581  -4.230   2.865  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.455  -3.894   4.897  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    4    2   43                                                  
CONECT    4    5    3   44                                                  
CONECT    5   11    6    4                                                  
CONECT    6    5    7   45                                                  
CONECT    7    6    8   46                                                  
CONECT    8    9   10    7                                                  
CONECT    9    8   47                                                       
CONECT   10    8   11   48                                                  
CONECT   11    5   10   49                                                  
CONECT   12    2   13                                                       
CONECT   13   12   14   50   51                                             
CONECT   14   41   15   13   52                                             
CONECT   15   14   16                                                       
CONECT   16   37   15   17   53                                             
CONECT   17   18   16                                                       
CONECT   18   36   19   17                                                  
CONECT   19   18   20   54                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20   55                                                       
CONECT   22   23   35   20                                                  
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26   56                                                  
CONECT   26   25   34   27                                                  
CONECT   27   28   33   26                                                  
CONECT   28   27   29   57                                                  
CONECT   29   28   30   58                                                  
CONECT   30   29   32   31                                                  
CONECT   31   30   59                                                       
CONECT   32   30   33   60                                                  
CONECT   33   32   27   61                                                  
CONECT   34   35   26                                                       
CONECT   35   34   22   36                                                  
CONECT   36   35   18   62                                                  
CONECT   37   38   16   39   63                                             
CONECT   38   37   64                                                       
CONECT   39   40   37   41   65                                             
CONECT   40   39   66                                                       
CONECT   41   42   39   14   67                                             
CONECT   42   41   68                                                       
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    6                                                            
CONECT   46    7                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   11                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   16                                                            
CONECT   54   19                                                            
CONECT   55   21                                                            
CONECT   56   25                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   33                                                            
CONECT   62   36                                                            
CONECT   63   37                                                            
CONECT   64   38                                                            
CONECT   65   39                                                            
CONECT   66   40                                                            
CONECT   67   41                                                            
CONECT   68   42                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
Echinacina b	MeSH

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(\C([H])=C(/[H])C(=O)OC([H])([H])[C@@]2([H])O[C@@]([H])(OC3=C([H])C(O[H])=C4C(=O)C([H])=C(OC4=C3[H])C3=C([H])C([H])=C(O[H])C([H])=C3[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]2([H])O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3+/t24-,27-,28+,29-,30-/m1/s1

InChI Key

WPQRDUGBKUNFJW-ZZSHFKPLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cucumis sativus L.	Plant	KNApSAcK
Echinop echinatus	-	KNApSAcK
Echinops echinatus	LOTUS Database	35616633
Lagopsis supina	Plant	KNApSAcK
Leucas aspera	LOTUS Database	35616633
Leucas cephalotes	LOTUS Database	35616633
Leucas neuflizeana	LOTUS Database	35616633
Marrubium vulgare	LOTUS Database	35616633
Phlomis floccosa	LOTUS Database	35616633
Pogostemon cablin	Plant	KNApSAcK
Populus tremuloides	LOTUS Database	35616633
Potentilla fruticosa	LOTUS Database	35616633
Scolopia chinensis	LOTUS Database	35616633
Sideritis syriaca	LOTUS Database	35616633
Stachys aegyptiaca	LOTUS Database	35616633
Stachys alopecuros	Plant	KNApSAcK
Stachys anisochila Vis.et Panc.	Plant	KNApSAcK
Stachys bombycina	LOTUS Database	35616633
Stachys byzantina	JEOL database	Demirtas, I., et al, Phytochem. Lett. 6, 209 (2013)
Stachys germanica L.	Plant	KNApSAcK
Stachys lanata	Plant	KNApSAcK
Stachys ocymastrum	LOTUS Database	35616633
Stachys officinalis (L.) Trev.	Plant	KNApSAcK
Stachys palustris L.	Plant	KNApSAcK
Stachys plumosa Griseb.	Plant	KNApSAcK
Stachys scardica Griseb.	Plant	KNApSAcK
Stachys sylvatica	Plant	KNApSAcK
Tinospora crispa	LOTUS Database	35616633
Turnera diffusa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Coumaric acid ester
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Chromone
Glycosyl compound
1-benzopyran
Benzopyran
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Pyran
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
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	2.91	ALOGPS
logP	3.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.61 m³·mol⁻¹	ChemAxon
Polarizability	56.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

4944309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439941

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao J, Dasmahapatra AK, Khan SI, Khan IA: Anti-aromatase activity of the constituents from damiana (Turnera diffusa). J Ethnopharmacol. 2008 Dec 8;120(3):387-93. doi: 10.1016/j.jep.2008.09.016. Epub 2008 Sep 26. [PubMed:18948180 ]
Shah SA, Sander S, White CM, Rinaldi M, Coleman CI: Evaluation of echinacea for the prevention and treatment of the common cold: a meta-analysis. Lancet Infect Dis. 2007 Jul;7(7):473-80. doi: 10.1016/S1473-3099(07)70160-3. [PubMed:17597571 ]
Heinen-Kammerer T, Holtmannspotter C, Schnabel S, Motzkat K, Kiencke P, Rychlik R: [Effectiveness of echinacin in therapy of chronic recurrent respiratory disease]. Gesundheitswesen. 2005 Apr;67(4):296-301. doi: 10.1055/s-2005-858135. [PubMed:15856390 ]
Demirtas, I., et al. (2013). Demirtas, I., et al, Phytochem. Lett. 6, 209 (2013) . Phytochem..

Showing NP-Card for apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside (NP0042161)

MOL for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

3D MOL for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

3D SDF for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

3D-SDF for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

PDB for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

3D PDB for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

SMILES for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

INCHI for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

Structure for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)

3D Structure for NP0042161 (apigenin 7-O-beta-D-(6''-trans-p-coumaroyl) glucoside)