NP-MRD: Showing NP-Card for 5,3'-dihydroxy-6,7,4'-trimethoxyflavone (NP0024992)

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Record Information

Version

2.0

Created at

2021-06-19 17:13:48 UTC

Updated at

2021-06-29 23:49:39 UTC

NP-MRD ID

NP0024992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,3'-dihydroxy-6,7,4'-trimethoxyflavone

Provided By

JEOL Database JEOL Logo

Description

Eupatorin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, eupatorin is considered to be a flavonoid. Eupatorin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5,3'-dihydroxy-6,7,4'-trimethoxyflavone is found in Achillea collina, Achillea formosa, Achillea nobilis, Achillea setacea, Ageratina pichinchensis, Aloysia citrodora, Artemisia annua, Artemisia argyi, Baccharis genistelloides, Baccharis sagittalis, Brickellia dentata, Carphochaete bigelovii, Centaurea aggregata, Centaurea arenaria, Centaurea cadmea, Centaurea cuneifolia, Centaurea decipiens, Centaurea inermis, Chrysanthemum morifolium, Citrus reticulata, Condea tomentosa, Eupatorium album, Ageratina altissima, Ferula aucheri, Isodon umbrosus, Lantana montevidensis, Liatris aspera, Mentha piperita, Merillia caloxylon, Merrillia caloxylon, Ocimum basilicum, Phyla dulcis, Rudbeckia subtomentosa, Salvia limbata, Salvia mirzayanii, Salvia sahendica, Sideritis ferrensis, Sideritis nutans, Stevia origanoides, Tanacetum parthenium, Tanacetum vulgare, Teucrium nudicaule, Teucrium oliverianum, Teucrium orientale, Teucrium polium, Thymus vulgaris, Veronica officinalis , Veronica orchidea, Veronica teucrium and Vitex agnus-castus. 5,3'-dihydroxy-6,7,4'-trimethoxyflavone was first documented in 2008 (PMID: 18454852). Based on a literature review a small amount of articles have been published on Eupatorin (PMID: 19601638) (PMID: 22227008) (PMID: 22516932) (PMID: 22698713).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119133D          

 41 43  0  0  0  0            999 V2000
    2.1402   -1.6800    6.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -1.5326    6.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.9068    5.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554   -0.4123    4.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    0.2079    3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.3500    3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    0.9991    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.8815    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    2.5016    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835    3.3155    1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    2.1058   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6303   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    3.5449   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    2.2129   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912    2.7646   -3.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    2.0573   -4.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    1.2934   -2.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.9607   -3.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    0.1333   -3.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.7757   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    1.1838   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518    0.6331    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8332   -0.1581    4.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.7723    5.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.2529    6.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7049    6.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -2.3038    5.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -2.1883    7.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4893    4.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.5892    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    2.1835    3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.7507   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2834    2.1718   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    0.9952   -4.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    2.4848   -5.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973    0.5926   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.8659   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1026    0.0237   -4.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0542   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.0959    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.6391    7.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  2  0  0  0  0
  6  5  2  0  0  0  0
 17 20  1  0  0  0  0
  5  4  1  0  0  0  0
 14 12  1  0  0  0  0
  4  3  2  0  0  0  0
 12 11  2  0  0  0  0
  3 24  1  0  0  0  0
 21 20  2  0  0  0  0
 24 23  2  0  0  0  0
 23  6  1  0  0  0  0
  7  6  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 17 18  1  0  0  0  0
  8  7  2  0  0  0  0
 12 13  1  0  0  0  0
  7 22  1  0  0  0  0
 24 25  1  0  0  0  0
 21 11  1  0  0  0  0
 18 19  1  0  0  0  0
  9 10  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 20 39  1  0  0  0  0
  8 31  1  0  0  0  0
  5 30  1  0  0  0  0
  4 29  1  0  0  0  0
 23 40  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 13 32  1  0  0  0  0
 25 41  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    2.1402   -1.6800    6.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -1.5326    6.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.9068    5.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554   -0.4123    4.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    0.2079    3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.3500    3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    0.9991    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.8815    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    2.5016    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835    3.3155    1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    2.1058   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6303   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    3.5449   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    2.2129   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912    2.7646   -3.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    2.0573   -4.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    1.2934   -2.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.9607   -3.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    0.1333   -3.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.7757   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    1.1838   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518    0.6331    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8332   -0.1581    4.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.7723    5.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.2529    6.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7049    6.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -2.3038    5.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -2.1883    7.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4893    4.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.5892    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    2.1835    3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.7507   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2834    2.1718   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    0.9952   -4.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    2.4848   -5.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973    0.5926   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.8659   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1026    0.0237   -4.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0542   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.0959    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.6391    7.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  2  0
  6  5  2  0
 17 20  1  0
  5  4  1  0
 14 12  1  0
  4  3  2  0
 12 11  2  0
  3 24  1  0
 21 20  2  0
 24 23  2  0
 23  6  1  0
  7  6  1  0
 21 22  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  9  8  1  0
 17 18  1  0
  8  7  2  0
 12 13  1  0
  7 22  1  0
 24 25  1  0
 21 11  1  0
 18 19  1  0
  9 10  2  0
 14 15  1  0
 15 16  1  0
 20 39  1  0
  8 31  1  0
  5 30  1  0
  4 29  1  0
 23 40  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 13 32  1  0
 25 41  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END


  Mrv1652306192119133D          

 41 43  0  0  0  0            999 V2000
    2.1402   -1.6800    6.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -1.5326    6.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.9068    5.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554   -0.4123    4.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    0.2079    3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.3500    3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    0.9991    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.8815    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    2.5016    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835    3.3155    1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    2.1058   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6303   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    3.5449   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    2.2129   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912    2.7646   -3.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    2.0573   -4.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    1.2934   -2.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.9607   -3.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    0.1333   -3.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.7757   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    1.1838   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518    0.6331    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8332   -0.1581    4.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.7723    5.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.2529    6.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7049    6.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -2.3038    5.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -2.1883    7.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4893    4.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.5892    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    2.1835    3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.7507   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2834    2.1718   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    0.9952   -4.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    2.4848   -5.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973    0.5926   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.8659   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1026    0.0237   -4.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0542   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.0959    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.6391    7.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  2  0  0  0  0
  6  5  2  0  0  0  0
 17 20  1  0  0  0  0
  5  4  1  0  0  0  0
 14 12  1  0  0  0  0
  4  3  2  0  0  0  0
 12 11  2  0  0  0  0
  3 24  1  0  0  0  0
 21 20  2  0  0  0  0
 24 23  2  0  0  0  0
 23  6  1  0  0  0  0
  7  6  1  0  0  0  0
 21 22  1  0  0  0  0
  3  2  1  0  0  0  0
 11  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  8  1  0  0  0  0
 17 18  1  0  0  0  0
  8  7  2  0  0  0  0
 12 13  1  0  0  0  0
  7 22  1  0  0  0  0
 24 25  1  0  0  0  0
 21 11  1  0  0  0  0
 18 19  1  0  0  0  0
  9 10  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 20 39  1  0  0  0  0
  8 31  1  0  0  0  0
  5 30  1  0  0  0  0
  4 29  1  0  0  0  0
 23 40  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 13 32  1  0  0  0  0
 25 41  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

> <INCHI_KEY>
KLAOKWJLUQKWIF-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.00756703042816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.558498364200261

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.926435900548595

> <JCHEM_PKA_STRONGEST_BASIC>
-4.400005126544863

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eupatorin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    2.1402   -1.6800    6.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -1.5326    6.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.9068    5.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554   -0.4123    4.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    0.2079    3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.3500    3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    0.9991    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.8815    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    2.5016    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835    3.3155    1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    2.1058   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6303   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    3.5449   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    2.2129   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912    2.7646   -3.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    2.0573   -4.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    1.2934   -2.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.9607   -3.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    0.1333   -3.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.7757   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    1.1838   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518    0.6331    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8332   -0.1581    4.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.7723    5.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.2529    6.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7049    6.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -2.3038    5.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -2.1883    7.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4893    4.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.5892    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    2.1835    3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.7507   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2834    2.1718   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    0.9952   -4.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    2.4848   -5.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973    0.5926   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.8659   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1026    0.0237   -4.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0542   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.0959    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.6391    7.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  2  0
  6  5  2  0
 17 20  1  0
  5  4  1  0
 14 12  1  0
  4  3  2  0
 12 11  2  0
  3 24  1  0
 21 20  2  0
 24 23  2  0
 23  6  1  0
  7  6  1  0
 21 22  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  9  8  1  0
 17 18  1  0
  8  7  2  0
 12 13  1  0
  7 22  1  0
 24 25  1  0
 21 11  1  0
 18 19  1  0
  9 10  2  0
 14 15  1  0
 15 16  1  0
 20 39  1  0
  8 31  1  0
  5 30  1  0
  4 29  1  0
 23 40  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 13 32  1  0
 25 41  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       2.140  -1.680   6.664  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.726  -1.533   6.604  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.221  -0.907   5.495  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.955  -0.412   4.420  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.297   0.208   3.348  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.101   0.350   3.334  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.765   0.999   2.188  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.760   1.882   2.358  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.372   2.502   1.175  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.284   3.316   1.277  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.848   2.106  -0.138  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.366   2.630  -1.325  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.389   3.545  -1.332  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.830   2.213  -2.550  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.291   2.765  -3.723  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.444   2.057  -4.176  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.766   1.293  -2.598  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.310   0.961  -3.847  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.158   0.133  -3.928  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.263   0.776  -1.401  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.805   1.184  -0.178  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.252   0.633   0.953  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.833  -0.158   4.413  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.171  -0.772   5.472  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.925  -1.253   6.509  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.638  -0.705   6.674  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.507  -2.304   5.842  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.383  -2.188   7.602  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.037  -0.489   4.378  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.893   0.589   2.520  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.146   2.184   3.323  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.634   3.751  -0.403  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.283   2.172  -3.483  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.224   0.995  -4.333  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.741   2.485  -5.139  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.697   0.593  -3.420  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.364  -0.866  -3.530  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.103   0.024  -4.985  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.453   0.054  -1.387  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.918  -0.096   4.442  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.280  -1.639   7.133  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    4   24    2                                                  
CONECT    4    5    3   29                                                  
CONECT    5    6    4   30                                                  
CONECT    6    5   23    7                                                  
CONECT    7    6    8   22                                                  
CONECT    8    9    7   31                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12    9   21                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   32                                                       
CONECT   14   17   12   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   33   34   35                                             
CONECT   17   14   20   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   36   37   38                                             
CONECT   20   17   21   39                                                  
CONECT   21   20   22   11                                                  
CONECT   22   21    7                                                       
CONECT   23   24    6   40                                                  
CONECT   24    3   23   25                                                  
CONECT   25   24   41                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    8                                                            
CONECT   32   13                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
CONECT   39   20                                                            
CONECT   40   23                                                            
CONECT   41   25                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    2.1402   -1.6800    6.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259   -1.5326    6.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.9068    5.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554   -0.4123    4.4199 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2972    0.2079    3.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    0.3500    3.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7652    0.9991    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    1.8815    2.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    2.5016    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835    3.3155    1.2770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    2.1058   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657    2.6303   -1.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    3.5449   -1.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8302    2.2129   -2.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912    2.7646   -3.7231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    2.0573   -4.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    1.2934   -2.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099    0.9607   -3.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575    0.1333   -3.9275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2632    0.7757   -1.4011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8046    1.1838   -0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2518    0.6331    0.9530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8332   -0.1581    4.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.7723    5.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248   -1.2529    6.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384   -0.7049    6.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066   -2.3038    5.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3833   -2.1883    7.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4893    4.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    0.5892    2.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1459    2.1835    3.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6338    3.7507   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2834    2.1718   -3.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    0.9952   -4.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7414    2.4848   -5.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6973    0.5926   -3.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635   -0.8659   -3.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1026    0.0237   -4.9847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531    0.0542   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9176   -0.0959    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798   -1.6391    7.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  2  0
  6  5  2  0
 17 20  1  0
  5  4  1  0
 14 12  1  0
  4  3  2  0
 12 11  2  0
  3 24  1  0
 21 20  2  0
 24 23  2  0
 23  6  1  0
  7  6  1  0
 21 22  1  0
  3  2  1  0
 11  9  1  0
  2  1  1  0
  9  8  1  0
 17 18  1  0
  8  7  2  0
 12 13  1  0
  7 22  1  0
 24 25  1  0
 21 11  1  0
 18 19  1  0
  9 10  2  0
 14 15  1  0
 15 16  1  0
 20 39  1  0
  8 31  1  0
  5 30  1  0
  4 29  1  0
 23 40  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 13 32  1  0
 25 41  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
3',5-Dihydroxy-4',6,7-trimethoxyflavone	ChEBI
Eupatorine	ChEBI

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3154 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

Traditional Name

eupatorin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C1=C([H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C2O1

InChI Identifier

InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3

InChI Key

KLAOKWJLUQKWIF-UHFFFAOYSA-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
Achillea collina	LOTUS Database	35616633
Achillea formosa	LOTUS Database	35616633
Achillea nobilis	LOTUS Database	35616633
Achillea santolina	KNApSAcK Database	22123792
Achillea setacea	LOTUS Database	35616633
Ageratina pichinchensis	Plant	KNApSAcK
Aloysia citrodora	LOTUS Database	35616633
Arnica longifolia	KNApSAcK Database	22123792
Artemisia annua	LOTUS Database	35616633
Artemisia argyi	LOTUS Database	35616633
Baccharis genistelloides	LOTUS Database	35616633
Baccharis sagittalis	LOTUS Database	35616633
Baccharis trimera	KNApSAcK Database	22123792
Brickellia baccharidea	KNApSAcK Database	22123792
Brickellia dentata	LOTUS Database	35616633
Carphochaete bigelovii	LOTUS Database	35616633
Centaurea aggregata	LOTUS Database	35616633
Centaurea arenaria	LOTUS Database	35616633
Centaurea cadmea	LOTUS Database	35616633
Centaurea cuneifolia	LOTUS Database	35616633
Centaurea decipiens	LOTUS Database	35616633
Centaurea inermis	LOTUS Database	35616633
Chromolaena arnottiana	KNApSAcK Database	22123792
Chrysanthemum morifolium	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Condea tomentosa	LOTUS Database	35616633
Dorema aucherii	KNApSAcK Database	22123792
Eupatorium album	LOTUS Database	35616633
Eupatorium altissimum	KNApSAcK Database	22123792
Eupatorium rugosum	LOTUS Database	35616633
Eupatorium semiserratum	KNApSAcK Database	22123792
Ferula aucheri	LOTUS Database	35616633
Isodon umbrosus	LOTUS Database	35616633
Lantana montevidensis	LOTUS Database	35616633
Liatris aspera	LOTUS Database	35616633
Lippia citriodora	KNApSAcK Database	22123792
Lippia dulcis TREV.	KNApSAcK Database	22123792
Mentha piperita	LOTUS Database	35616633
Mentha x piperita	KNApSAcK Database	22123792
Merillia caloxylon	-	KNApSAcK
Merrillia caloxylon	LOTUS Database	35616633
Mikania minima	KNApSAcK Database	22123792
Ocimum basilicum	LOTUS Database	35616633
Ocimum spp.	KNApSAcK Database	22123792
Orthosiphon aristatus	KNApSAcK Database	22123792
Orthosiphon spicatus	KNApSAcK Database	22123792
Orthosiphon stamineus	KNApSAcK Database	22123792
Phyla dulcis	LOTUS Database	35616633
Plectranthus fruticosus	KNApSAcK Database	22123792
Rudbeckia subtomentosa	LOTUS Database	35616633
Salvia lavandulaefolia	KNApSAcK Database	22123792
Salvia lavandulifolia	KNApSAcK Database	22123792
Salvia limbata	LOTUS Database	35616633
Salvia macrosiphon	KNApSAcK Database	22123792
Salvia mirzayana	KNApSAcK Database	22123792
Salvia mirzayanii	LOTUS Database	35616633
Salvia moorcroftiana	KNApSAcK Database	22123792
Salvia plebeia	KNApSAcK Database	22123792
Salvia sahendica	LOTUS Database	35616633
Salvia syriaca	KNApSAcK Database	22123792
Sideritis angustifolia	KNApSAcK Database	22123792
Sideritis ferrensis	LOTUS Database	35616633
Sideritis nutans	LOTUS Database	35616633
Sideritis spp.	KNApSAcK Database	22123792
Stevia origanoides	LOTUS Database	35616633
Stevia rebaudiana	KNApSAcK Database	22123792
Tanacetum parthenium	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Teucrium nudicaule	LOTUS Database	35616633
Teucrium oliverianum	LOTUS Database	35616633
Teucrium orientale	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Thymus vulgaris	LOTUS Database	35616633
Trichostema lanatum	KNApSAcK Database	22123792
Vernonia saligna	KNApSAcK Database	22123792
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK
Vitex agnus-castus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Not Available

Substituents

Not Available

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	2.95	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	35.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0252128

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001539

KNApSAcK ID

C00003894

Chemspider ID

87743

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97214

PDB ID

Not Available

ChEBI ID

136666

Good Scents ID

rw1700781

References

General References

Androutsopoulos V, Arroo RR, Hall JF, Surichan S, Potter GA: Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism. Breast Cancer Res. 2008;10(3):R39. doi: 10.1186/bcr2090. Epub 2008 May 2. [PubMed:18454852 ]
Androutsopoulos VP, Li N, Arroo RR: The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells. J Nat Prod. 2009 Aug;72(8):1390-4. doi: 10.1021/np900051s. [PubMed:19601638 ]
Salmela AL, Pouwels J, Kukkonen-Macchi A, Waris S, Toivonen P, Jaakkola K, Maki-Jouppila J, Kallio L, Kallio MJ: The flavonoid eupatorin inactivates the mitotic checkpoint leading to polyploidy and apoptosis. Exp Cell Res. 2012 Mar 10;318(5):578-92. doi: 10.1016/j.yexcr.2011.12.014. Epub 2011 Dec 29. [PubMed:22227008 ]
Laavola M, Nieminen R, Yam MF, Sadikun A, Asmawi MZ, Basir R, Welling J, Vapaatalo H, Korhonen R, Moilanen E: Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta Med. 2012 May;78(8):779-86. doi: 10.1055/s-0031-1298458. Epub 2012 Apr 19. [PubMed:22516932 ]
Doleckova I, Rarova L, Gruz J, Vondrusova M, Strnad M, Krystof V: Antiproliferative and antiangiogenic effects of flavone eupatorin, an active constituent of chloroform extract of Orthosiphon stamineus leaves. Fitoterapia. 2012 Sep;83(6):1000-7. doi: 10.1016/j.fitote.2012.06.002. Epub 2012 Jun 12. [PubMed:22698713 ]
Park, Y., et al. (2007). Park, Y., et al, Magn. Reson. Chem. 45, 1072 (2007). Mag. Reson. Chem..

Showing NP-Card for 5,3'-dihydroxy-6,7,4'-trimethoxyflavone (NP0024992)

MOL for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

3D MOL for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

3D SDF for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

3D-SDF for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

PDB for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

3D PDB for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

SMILES for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

INCHI for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

Structure for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)

3D Structure for NP0024992 (5,3'-dihydroxy-6,7,4'-trimethoxyflavone)