NP-MRD: Showing NP-Card for arctigenin (NP0209894)

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Record Information

Version

2.0

Created at

2022-09-05 07:29:19 UTC

Updated at

2022-09-05 07:29:20 UTC

NP-MRD ID

NP0209894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

arctigenin

Description

L-Arctigenin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. L-Arctigenin is an extremely weak basic (essentially neutral) compound (based on its pKa). It is the aglycone of arctiin. It has been found to act as an agonist of adiponectin receptor 1 (AdipoR1). The use of arctigenin has been shown to be effective in a mouse model of Japanese encephalitis. It has shown antiviral and anticancer effects in vitro. arctigenin is found in Arctium lappa, Bupleurum salicifolium, Centaurea arenaria, Centaurea calcitrapa, Centaurea dealbata, Centaurea deflexa, Centaurea melitensis, Centaurea phrygia, Centaurea regia, Centaurea scoparia, Daphne feddei, Forsythia intermedia, Forsythia koreana, Forsythia ovata, Ipomoea cairica, Saussurea involucrata, Saussurea medusa, Saussurea parviflora, Saussurea salicifolia, Taiwania cryptomerioides, Torreya nucifera, Trachelospermum asiaticum, Trachelospermum axillare and Wikstroemia indica. Arctigenin is a lignan found in certain plants of the Asteraceae, including the greater burdock (Arctium lappa) and Saussurea heteromalla.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516342D          

 27 29  0  0  0  0            999 V2000
    4.8946    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -6.5128   -0.1480   -1.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7428   -0.1891   -0.4646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6752   -0.4577    0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3875   -0.6896   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3399   -0.9556    0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632   -1.2101    0.3285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    0.0900    0.2614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7945    0.9752   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503    1.6724   -0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9720    0.9064   -1.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3820    0.7870   -1.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328   -0.1309   -0.1817 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2181    0.2781    0.8550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359    0.2071    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3060   -0.9846    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428   -1.0721    0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3025    0.0116   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6489   -0.1230   -0.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3207   -1.3547   -0.4565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6426    1.2075   -0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3496    2.2707   -1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6569    3.4880   -1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167    1.2737   -0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6409   -0.9777    2.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9110   -0.7497    2.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9479   -0.4864    1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2377   -0.2537    2.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7812    0.6733   -2.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4560    0.0352   -2.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0129   -1.0753   -2.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -0.6613   -1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331   -1.8339    1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -1.6844   -0.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479    0.5585    1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558    0.3393   -2.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    1.8070   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036   -1.1579   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0921   -0.4125    1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9705    1.2864    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111   -1.8537    1.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1318   -2.0406    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3829   -1.2908   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2652   -1.7168    0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8392   -2.1508   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220    3.8119   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    3.4608   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    4.2888   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8398    2.2269   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8715   -1.1793    2.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0950   -0.7783    3.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4058   -0.2801    3.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
  3  2  1  0
  2  1  1  0
  3  4  2  0
 14 23  1  0
 23 20  2  0
 20 21  1  0
 21 22  1  0
 20 17  1  0
  7 12  1  0
  4  5  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 16 41  1  0
 15 40  1  0
 13 38  1  0
 13 39  1  0
 12 37  1  6
 11 35  1  0
 11 36  1  0
  7 34  1  1
  6 32  1  0
  6 33  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
 23 48  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
M  END


  Mrv1533004191516342D          

 27 29  0  0  0  0            999 V2000
    4.8946    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2COC(=O)C2CC2=CC=C(O)C(OC)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3

> <INCHI_KEY>
NQWVSMVXKMHKTF-UHFFFAOYSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.417

> <EXACT_MASS>
372.157288493

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.017602973130806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.4376765669999996

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945546155194782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.414892891268763

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
100.11670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arctigenin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       9.137   3.735   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.572  -4.795   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.127  -6.041   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.740   2.219   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.204   1.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.469   3.735   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.803   4.505   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   15                                                       
CONECT   24    6   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₆

Average Mass

372.4170 Da

Monoisotopic Mass

372.15729 Da

IUPAC Name

4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

arctigenin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2COC(=O)C2CC2=CC=C(O)C(OC)=C2)C=C1OC

InChI Identifier

InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3

InChI Key

NQWVSMVXKMHKTF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arctium lappa	LOTUS Database	35616633
Bupleurum salicifolium	LOTUS Database	35616633
Centaurea arenaria	LOTUS Database	35616633
Centaurea calcitrapa	LOTUS Database	35616633
Centaurea dealbata	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Centaurea melitensis	LOTUS Database	35616633
Centaurea phrygia	LOTUS Database	35616633
Centaurea regia	LOTUS Database	35616633
Centaurea scoparia	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Forsythia intermedia	LOTUS Database	35616633
Forsythia koreana	LOTUS Database	35616633
Forsythia ovata	LOTUS Database	35616633
Ipomoea cairica	LOTUS Database	35616633
Saussurea involucrata	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Saussurea parviflora	LOTUS Database	35616633
Saussurea salicifolia	LOTUS Database	35616633
Taiwania cryptomerioides	LOTUS Database	35616633
Torreya nucifera	LOTUS Database	35616633
Trachelospermum asiaticum	LOTUS Database	35616633
Trachelospermum axillare	LOTUS Database	35616633
Wikstroemia indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.2	ALOGPS
logP	3.44	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.12 m³·mol⁻¹	ChemAxon
Polarizability	39.02 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arctigenin

METLIN ID

Not Available

PubChem Compound

230232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for arctigenin (NP0209894)

MOL for NP0209894 (arctigenin)

3D MOL for NP0209894 (arctigenin)

3D SDF for NP0209894 (arctigenin)

3D-SDF for NP0209894 (arctigenin)

PDB for NP0209894 (arctigenin)

3D PDB for NP0209894 (arctigenin)

SMILES for NP0209894 (arctigenin)

INCHI for NP0209894 (arctigenin)

Structure for NP0209894 (arctigenin)

3D Structure for NP0209894 (arctigenin)