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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:40 UTC

Update Date

2022-03-07 02:52:25 UTC

HMDB ID

HMDB0030087

Secondary Accession Numbers

HMDB30087

Metabolite Identification

Common Name

(-)-Arctigenin

Description

(-)-Arctigenin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-Arctigenin is found, on average, in the highest concentration within burdocks (Arctium lappa) and sesames (Sesamum orientale) (-)-Arctigenin has also been detected, but not quantified in, cardoons (Cynara cardunculus) and grape wine. This could make (-)-arctigenin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-Arctigenin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

 
  Mrv1652309271714122D          

 27 29  0  0  1  0            999 V2000
   14.7787  -14.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9503  -14.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4938  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0328  -13.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2352  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6922  -13.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2047  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3625  -13.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7308  -13.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5202  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2013  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5202  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6314  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -13.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0903  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -13.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6314  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0903  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3463  -13.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3752  -13.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -12.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0937  -12.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3745  -12.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -12.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6280  -12.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6  8  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 23  1  0  0  0  0
  1  2  1  0  0  0  0
 23 24  1  0  0  0  0
  1  3  1  6  0  0  0
 22 25  1  0  0  0  0
  1  4  1  0  0  0  0
 16 26  1  0  0  0  0
  2  5  1  1  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0030087
     RDKit          3D
(-)-Arctigenin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.4819    0.0292    0.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3891   -1.1269    0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -1.7104   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -1.2091    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -1.8192   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -1.2835   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.2127   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9240   -0.5561   -2.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4631   -1.4318   -3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    0.3487   -3.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372    1.0996   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142    0.2283   -0.8074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5486    0.9552    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9767    1.3334    0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    2.5360    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7910    2.8739    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6805    2.0302    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    2.3792    1.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4524    3.6110    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    0.8191    1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446   -0.0201    2.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8117   -1.2791    2.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.5039    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -2.9530   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -3.4795   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -2.8578   -1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6036   -3.3939   -1.3469 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544   -0.2880    2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4419    0.5687    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143    0.6704    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -0.3217    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362   -0.8778    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -2.1188   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.6828   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    2.0520   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981    1.2718   -2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.6428   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.2868    1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926    1.8451    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    3.2537   -0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871    3.8296   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5314    3.7855    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573    4.3999    1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1686    3.6718   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6854   -1.9719    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880   -1.2308    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0429   -1.7604    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.4407    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294   -3.4779   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -4.3737   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -4.2285   -1.9093 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  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 12  7  1  0
 23 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END

 
  Mrv1652309271714122D          

 27 29  0  0  1  0            999 V2000
   14.7787  -14.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9503  -14.6090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4938  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0328  -13.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2352  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6922  -13.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2047  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3625  -13.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7308  -13.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5202  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2013  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -15.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5202  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6314  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -13.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0903  -14.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -13.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6314  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0903  -13.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3463  -13.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3752  -13.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -12.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0937  -12.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3745  -12.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9163  -12.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6280  -12.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 17 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
  6  8  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 23  1  0  0  0  0
  1  2  1  0  0  0  0
 23 24  1  0  0  0  0
  1  3  1  6  0  0  0
 22 25  1  0  0  0  0
  1  4  1  0  0  0  0
 16 26  1  0  0  0  0
  2  5  1  1  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030087

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=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/t15-,16+/m0/s1

> <INCHI_KEY>
NQWVSMVXKMHKTF-JKSUJKDBSA-N

> <FORMULA>
C21H24O6

> <MOLECULAR_WEIGHT>
372.4117

> <EXACT_MASS>
372.1572885

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.86932230092339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-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>
100.11670000000004

> <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

$$$$

HMDB0030087
     RDKit          3D
(-)-Arctigenin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.4819    0.0292    0.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3891   -1.1269    0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -1.7104   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -1.2091    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -1.8192   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -1.2835   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.2127   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9240   -0.5561   -2.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4631   -1.4318   -3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    0.3487   -3.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372    1.0996   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142    0.2283   -0.8074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5486    0.9552    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9767    1.3334    0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    2.5360    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7910    2.8739    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6805    2.0302    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    2.3792    1.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4524    3.6110    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    0.8191    1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446   -0.0201    2.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8117   -1.2791    2.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.5039    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -2.9530   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -3.4795   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -2.8578   -1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6036   -3.3939   -1.3469 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544   -0.2880    2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4419    0.5687    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143    0.6704    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -0.3217    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362   -0.8778    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -2.1188   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.6828   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    2.0520   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981    1.2718   -2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.6428   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.2868    1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926    1.8451    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    3.2537   -0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871    3.8296   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5314    3.7855    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573    4.3999    1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1686    3.6718   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6854   -1.9719    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880   -1.2308    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0429   -1.7604    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.4407    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294   -3.4779   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -4.3737   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -4.2285   -1.9093 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  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 12  7  1  0
 23 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  C   UNK     0      27.587 -27.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.041 -27.270   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.922 -28.047   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.061 -25.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.706 -28.047   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.559 -25.815   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.249 -27.270   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      26.810 -24.903   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.364 -25.038   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      23.371 -27.270   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.577 -28.047   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.242 -25.730   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.037 -28.047   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.371 -25.730   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.912 -27.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.577 -24.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.702 -27.270   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.037 -24.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.912 -25.730   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.702 -25.730   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      34.246 -24.961   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      19.367 -24.961   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      22.037 -23.434   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.708 -22.666   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.366 -23.427   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      31.577 -23.427   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      32.906 -22.660   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    6    1    5                                                  
CONECT    3    7    1                                                       
CONECT    4    8    9    1                                                  
CONECT    5   10    2                                                       
CONECT    6    2    8                                                       
CONECT    7    3   11   12                                                  
CONECT    8    4    6                                                       
CONECT    9    4                                                            
CONECT   10    5   13   14                                                  
CONECT   11    7   15                                                       
CONECT   12    7   16                                                       
CONECT   13   10   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   19   26                                                  
CONECT   17   13   20                                                       
CONECT   18   14   20   23                                                  
CONECT   19   15   21   16                                                  
CONECT   20   17   22   18                                                  
CONECT   21   19                                                            
CONECT   22   20   25                                                       
CONECT   23   18   24                                                       
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   16   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0030087
HETATM    1  C1  UNL     1       6.482   0.029   0.968  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.389  -1.127   0.180  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.227  -1.710  -0.275  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.973  -1.209   0.001  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.806  -1.819  -0.472  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.466  -1.283  -0.153  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.028  -0.213  -1.076  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.924  -0.556  -2.499  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.463  -1.432  -3.213  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.011   0.349  -3.057  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.637   1.100  -2.026  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.414   0.228  -0.807  1.00  0.00           C  
HETATM   13  C10 UNL     1      -0.549   0.955   0.487  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.977   1.333   0.644  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.463   2.536   0.175  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.791   2.874   0.325  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.680   2.030   0.944  1.00  0.00           C  
HETATM   18  O4  UNL     1      -6.020   2.379   1.092  1.00  0.00           O  
HETATM   19  C15 UNL     1      -6.452   3.611   0.597  1.00  0.00           C  
HETATM   20  C16 UNL     1      -4.222   0.819   1.423  1.00  0.00           C  
HETATM   21  O5  UNL     1      -5.145  -0.020   2.048  1.00  0.00           O  
HETATM   22  C17 UNL     1      -4.812  -1.279   2.580  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.907   0.504   1.266  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.972  -2.953  -1.232  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.214  -3.480  -1.526  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.341  -2.858  -1.047  1.00  0.00           C  
HETATM   27  O6  UNL     1       6.604  -3.394  -1.347  1.00  0.00           O  
HETATM   28  H1  UNL     1       6.454  -0.288   2.043  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.442   0.569   0.824  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.614   0.670   0.774  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.855  -0.322   0.598  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.536  -0.878   0.895  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.714  -2.119  -0.052  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.666   0.683  -0.895  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.049   2.052  -1.955  1.00  0.00           H  
HETATM   36  H9  UNL     1      -1.698   1.272  -2.255  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.070  -0.643  -0.908  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.292   0.287   1.307  1.00  0.00           H  
HETATM   39  H12 UNL     1       0.093   1.845   0.489  1.00  0.00           H  
HETATM   40  H13 UNL     1      -1.806   3.254  -0.328  1.00  0.00           H  
HETATM   41  H14 UNL     1      -4.187   3.830  -0.045  1.00  0.00           H  
HETATM   42  H15 UNL     1      -7.531   3.786   0.743  1.00  0.00           H  
HETATM   43  H16 UNL     1      -5.857   4.400   1.144  1.00  0.00           H  
HETATM   44  H17 UNL     1      -6.169   3.672  -0.492  1.00  0.00           H  
HETATM   45  H18 UNL     1      -5.685  -1.972   2.596  1.00  0.00           H  
HETATM   46  H19 UNL     1      -4.388  -1.231   3.603  1.00  0.00           H  
HETATM   47  H20 UNL     1      -4.043  -1.760   1.931  1.00  0.00           H  
HETATM   48  H21 UNL     1      -2.523  -0.441   1.634  1.00  0.00           H  
HETATM   49  H22 UNL     1       2.129  -3.478  -1.615  1.00  0.00           H  
HETATM   50  H23 UNL     1       4.295  -4.374  -2.128  1.00  0.00           H  
HETATM   51  H24 UNL     1       6.671  -4.229  -1.909  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   31
CONECT    5    6   24   24
CONECT    6    7   32   33
CONECT    7    8   12   34
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   35   36
CONECT   12   13   37
CONECT   13   14   38   39
CONECT   14   15   15   23
CONECT   15   16   40
CONECT   16   17   17   41
CONECT   17   18   20
CONECT   18   19
CONECT   19   42   43   44
CONECT   20   21   23   23
CONECT   21   22
CONECT   22   45   46   47
CONECT   23   48
CONECT   24   25   49
CONECT   25   26   26   50
CONECT   26   27
CONECT   27   51
END

HMDB0030087
     RDKit          3D
(-)-Arctigenin
 51 53  0  0  0  0  0  0  0  0999 V2000
    6.4819    0.0292    0.9677 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3891   -1.1269    0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -1.7104   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -1.2091    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -1.8192   -0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -1.2835   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0276   -0.2127   -1.0755 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9240   -0.5561   -2.4993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4631   -1.4318   -3.2132 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115    0.3487   -3.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372    1.0996   -2.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4142    0.2283   -0.8074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5486    0.9552    0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9767    1.3334    0.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    2.5360    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7910    2.8739    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6805    2.0302    0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0197    2.3792    1.0915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4524    3.6110    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    0.8191    1.4233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446   -0.0201    2.0480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8117   -1.2791    2.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9074    0.5039    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9724   -2.9530   -1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2137   -3.4795   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -2.8578   -1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6036   -3.3939   -1.3469 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4544   -0.2880    2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4419    0.5687    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143    0.6704    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550   -0.3217    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5362   -0.8778    0.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -2.1188   -0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.6828   -0.8947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0490    2.0520   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6981    1.2718   -2.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0701   -0.6428   -0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917    0.2868    1.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0926    1.8451    0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064    3.2537   -0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871    3.8296   -0.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5314    3.7855    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8573    4.3999    1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1686    3.6718   -0.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6854   -1.9719    2.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3880   -1.2308    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0429   -1.7604    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -0.4407    1.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294   -3.4779   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2951   -4.3737   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710   -4.2285   -1.9093 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  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
 12  7  1  0
 23 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 27 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone	HMDB
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone	HMDB
Arctigenin	HMDB
(-)-Arctigenin	KEGG

Chemical Formula

C₂₁H₂₄O₆

Average Molecular Weight

372.4117

Monoisotopic Molecular Weight

372.1572885

IUPAC Name

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

Traditional Name

(-)-arctigenin

CAS Registry Number

7770-78-7

SMILES

COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=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/t15-,16+/m0/s1

InChI Key

NQWVSMVXKMHKTF-JKSUJKDBSA-N

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

lignan (CHEBI:79 )
Lignans (C10545 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030087)

Cellular substructure

Membrane (HMDB: HMDB0030087)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030087)

Source

Endogenous

Endogenous (HMDB: HMDB0030087)

Plant

Plant (HMDB: HMDB0030087)

Exogenous

Food

Food (HMDB: HMDB0030087)

Herb and spice

Oilseed crop

Sesame (FooDB: FOOD00170)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Shoot vegetable

Cardoon (FooDB: FOOD00319)

Process

Not Available

Role

Biological role

anti HIV (HMDB: HMDB0030087)
anti leukemic (HMDB: HMDB0030087)
anti lymphomic (HMDB: HMDB0030087)
anti proliferant (HMDB: HMDB0030087)
anti TNF (HMDB: HMDB0030087)
anti topoisomerase-II (HMDB: HMDB0030087)
antitumor (HMDB: HMDB0030087)
antiviral agent (HMDB: HMDB0030087)
cytotoxic (HMDB: HMDB0030087)
differentiator (HMDB: HMDB0030087)
immunological adjuvant (HMDB: HMDB0030087)

Modulator

Inhibitor

Enzyme inhibitor

antiintegrase (HMDB: HMDB0030087)
HIV-reverse-transcriptase inhibitor (HMDB: HMDB0030087)
immunomodulator (HMDB: HMDB0030087)
phosphodiesterase inhibitor (HMDB: HMDB0030087)
topoisomerase inhibitor (HMDB: HMDB0030087)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antiviral agent (HMDB: HMDB0030087)
immunological adjuvant (HMDB: HMDB0030087)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0030087)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	567.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	23.08 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.470 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
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	38.87 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	190.547	31661259
DarkChem	[M-H]-	187.647	31661259
DeepCCS	[M+H]+	182.768	30932474
DeepCCS	[M-H]-	180.41	30932474
DeepCCS	[M-2H]-	213.895	30932474
DeepCCS	[M+Na]+	189.113	30932474
AllCCS	[M+H]+	190.8	32859911
AllCCS	[M+H-H2O]+	187.7	32859911
AllCCS	[M+NH4]+	193.6	32859911
AllCCS	[M+Na]+	194.4	32859911
AllCCS	[M-H]-	193.5	32859911
AllCCS	[M+Na-2H]-	193.8	32859911
AllCCS	[M+HCOO]-	194.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Arctigenin	COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC	4925.3	Standard polar	33892256
(-)-Arctigenin	COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC	3131.4	Standard non polar	33892256
(-)-Arctigenin	COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC	3132.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Arctigenin,1TMS,isomer #1	COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)C=C1OC	3191.0	Semi standard non polar	33892256
(-)-Arctigenin,1TBDMS,isomer #1	COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C=C1OC	3433.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-0902000000-a82290112ad63ba03dcc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Arctigenin GC-MS (1 TMS) - 70eV, Positive	splash10-0kor-3973800000-2347d0d35e64e75b2b49	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-1900000000-94ffe376e556a84e04e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 20V, Positive-QTOF	splash10-000i-0911000000-2c7a991f2027b0e8dc39	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOF	splash10-052r-0928000000-178d921541b9d4503c6f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-0900000000-42290b1e66720d9e2353	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOF	splash10-000i-0900000000-72b4027a78652bdd8eb9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOF	splash10-000i-1900000000-7fb96b95e48e656b0645	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-0916000000-47e3d42e55329b017ba7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-0900000000-1642e59faff2457a7cff	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOF	splash10-000i-0916000000-fb82e62c5852184489ec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOF	splash10-000i-1900000000-ff811c876ea83a69a357	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-1900000000-6b50e0e0840d80baa1cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-1900000000-a9fd3c90bbf09fb0df59	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOF	splash10-000i-0926000000-2ab58c4998975ed5e47b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOF	splash10-000i-0900000000-0850a6604476178cdab0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 40V, Positive-QTOF	splash10-000i-0910000000-96f24efffea4aac77e10	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-0926000000-a8895984ec2ac4ab9465	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOF	splash10-000i-0910000000-9c2761b3ac042651bd73	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOF	splash10-000i-1900000000-0684d0cb19a0e2a2bb34	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOF	splash10-000i-0910000000-784cae6debd6285bdcbe	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOF	splash10-00di-0219000000-584468bac14267e31318	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 20V, Positive-QTOF	splash10-00bi-0849000000-e5165efc859c5b26acaa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 40V, Positive-QTOF	splash10-0h09-1900000000-c6366c49014c7cfa69a6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 10V, Negative-QTOF	splash10-00di-0009000000-1101ebe8048661a906d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 20V, Negative-QTOF	splash10-05dr-0219000000-6a116c084f4196a8e9ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Arctigenin 40V, Negative-QTOF	splash10-00or-0269000000-a57a1d2446d72c2c7c98	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Arctigenin

METLIN ID

Not Available

PubChem Compound

64981

PDB ID

Not Available

ChEBI ID

391051

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1486671

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .

Showing metabocard for (-)-Arctigenin (HMDB0030087)

MOL for HMDB0030087 ((-)-Arctigenin)

3D MOL for HMDB0030087 ((-)-Arctigenin)

3D SDF for HMDB0030087 ((-)-Arctigenin)

3D-SDF for HMDB0030087 ((-)-Arctigenin)

PDB for HMDB0030087 ((-)-Arctigenin)

3D PDB for HMDB0030087 ((-)-Arctigenin)

SMILES for HMDB0030087 ((-)-Arctigenin)

INCHI for HMDB0030087 ((-)-Arctigenin)

Structure for HMDB0030087 ((-)-Arctigenin)

3D Structure for HMDB0030087 ((-)-Arctigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra