NP-MRD: Showing NP-Card for (2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid (NP0285225)

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Record Information

Version

2.0

Created at

2022-09-09 13:18:00 UTC

Updated at

2022-09-09 13:18:01 UTC

NP-MRD ID

NP0285225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid

Description

Arctigenic acid, also known as arctigenate, belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. (2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid is found in Arctium lappa. (2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid was first documented in 2013 (PMID: 23519790). Based on a literature review a small amount of articles have been published on Arctigenic acid (PMID: 25636881) (PMID: 25274606) (PMID: 24434279).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215182D          

 28 29  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 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
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 15 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
    6.2165   -1.9088    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201   -0.7137    0.8063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6753   -0.0223    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8543   -0.4718   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994    0.2078   -0.9766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8944   -0.3496   -2.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -1.3490   -1.6281 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6078   -2.4792   -1.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6209   -2.6039    0.2300 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3001   -3.3974   -1.7597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1736   -0.8323   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1293   -1.9324   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524   -2.4338   -1.4283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.3036   -1.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728    0.8064   -0.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    1.7774    0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6406    2.2406    1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297    1.7516    1.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9348    2.1789    2.2962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7375    3.1702    3.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332    0.7779    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5249    0.2745    0.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8232   -0.7228   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2502    0.3130   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054    1.3541   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2032    1.8437    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    1.1327    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1803    1.5604    2.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8887   -2.4468    0.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7512   -1.6762   -0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3279   -2.5519    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1049   -1.3730   -1.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725    0.4827   -2.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606   -0.9205   -2.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3507   -1.7930   -2.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852   -3.4692   -1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -0.5056    0.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152   -1.5683    0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6196   -2.8034    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5853   -2.0380   -2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147   -0.0848   -2.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3726    1.1632   -1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643    2.2112    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3995    3.0142    2.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7131    3.5673    3.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    3.9470    2.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2712    2.6943    4.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2172   -1.6439   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5732   -0.3460   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9135   -0.9539   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -0.4532   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5345    1.9162   -0.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9663    2.7436    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285    2.4124    2.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  3  1  0
 24 15  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  6
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 10 36  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
M  END


  Mrv1652309092215182D          

 28 29  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 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
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  2  0  0  0  0
 15 24  1  0  0  0  0
  5 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@H]([C@H](CO)CC2=CC=C(OC)C(OC)=C2)C(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O7/c1-26-18-7-5-13(11-20(18)28-3)8-15(12-22)16(21(24)25)9-14-4-6-17(23)19(10-14)27-2/h4-7,10-11,15-16,22-23H,8-9,12H2,1-3H3,(H,24,25)/t15-,16+/m0/s1

> <INCHI_KEY>
WFRZWIDPAWVEAS-JKSUJKDBSA-N

> <FORMULA>
C21H26O7

> <MOLECULAR_WEIGHT>
390.432

> <EXACT_MASS>
390.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.30643868533164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid

> <JCHEM_LOGP>
2.773205442333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.946306466998758

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.818289985777329

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6105769050905563

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
103.6089

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   15                                                       
CONECT   25    5   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    3   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
Arctigenate	Generator

Chemical Formula

C₂₁H₂₆O₇

Average Mass

390.4320 Da

Monoisotopic Mass

390.16785 Da

IUPAC Name

(2R,3R)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid

Traditional Name

(2R,3R)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@H]([C@H](CO)CC2=CC=C(OC)C(OC)=C2)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C21H26O7/c1-26-18-7-5-13(11-20(18)28-3)8-15(12-22)16(21(24)25)9-14-4-6-17(23)19(10-14)27-2/h4-7,10-11,15-16,22-23H,8-9,12H2,1-3H3,(H,24,25)/t15-,16+/m0/s1

InChI Key

WFRZWIDPAWVEAS-JKSUJKDBSA-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

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
3-phenylpropanoic-acid
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.77	ChemAxon
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	103.61 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28282651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102397297

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu Z, Gu C, Wang K, Ju J, Wang H, Ruan K, Feng Y: Arctigenic acid, the key substance responsible for the hypoglycemic activity of Fructus Arctii. Phytomedicine. 2015 Jan 15;22(1):128-37. doi: 10.1016/j.phymed.2014.11.006. Epub 2014 Nov 22. [PubMed:25636881 ]
Gao Q, Zhang Y, Wo S, Zuo Z: Elucidation of arctigenin pharmacokinetics after intravenous and oral administrations in rats: integration of in vitro and in vivo findings via semi-mechanistic pharmacokinetic modeling. AAPS J. 2014 Nov;16(6):1321-33. doi: 10.1208/s12248-014-9664-x. Epub 2014 Oct 2. [PubMed:25274606 ]
Gao Q, Zhang Y, Wo S, Zuo Z: Extensive intestinal first-pass metabolism of arctigenin: evidenced by simultaneous monitoring of both parent drug and its major metabolites. J Pharm Biomed Anal. 2014 Mar;91:60-7. doi: 10.1016/j.jpba.2013.12.017. Epub 2013 Dec 25. [PubMed:24434279 ]
Gao Q, Zhang Y, Wo S, Zuo Z: Hydrolysis is the dominating in vivo metabolism pathway for arctigenin: identification of novel metabolites of arctigenin by LC/MS/MS after oral administration in rats. Planta Med. 2013 Apr;79(6):471-9. doi: 10.1055/s-0032-1328332. Epub 2013 Mar 21. [PubMed:23519790 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid (NP0285225)

MOL for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

3D MOL for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

3D SDF for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

3D-SDF for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

PDB for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

3D PDB for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

SMILES for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

INCHI for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

Structure for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)

3D Structure for NP0285225 ((2r,3r)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid)