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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:36:03 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036459

Secondary Accession Numbers

HMDB36459

Metabolite Identification

Common Name

Macelignan

Description

Macelignan belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. Macelignan has been detected, but not quantified in, herbs and spices. This could make macelignan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Macelignan.

Structure

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

HMDB0036459
     RDKit          3D
Macelignan
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8946    2.6778   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289    1.6262   -0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1020    0.5676    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    0.5377    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1079   -0.4862    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -0.4821    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893   -1.2101    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.7051    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734   -0.6646   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.4947   -1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645    0.6201   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.5385   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6183    0.1794   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952    0.1212   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444    0.4194    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    0.7777    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.8294    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026    1.0205    2.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059    1.1721    2.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2911    0.4484    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -1.5230    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2734   -1.5255    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8939   -0.4824    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2724   -0.4806    0.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.2839   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    3.4083   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677    3.1741   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942    1.4047   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    0.5599    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -0.9033    2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -1.2507    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084   -3.1750   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280   -2.7707   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -3.1854    1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9538   -1.4909   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625    0.5814   -2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.1725   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -0.7607   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391    1.0386   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    1.3604   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624   -0.0589   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.1613   -1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    1.1249    1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.6478    3.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998    2.2285    2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.3529    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323   -2.3224    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568    0.3104   -0.1594 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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
M  END


  Mrv0541 05061309092D          

 24 26  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   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
   -4.2868    0.8250    0.0000 C   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
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
 13  1  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  2  0  0  0  0
 16  5  1  0  0  0  0
 16  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 19 10  1  0  0  0  0
 19 17  2  0  0  0  0
 20 11  1  0  0  0  0
 20 18  2  0  0  0  0
 21 17  1  0  0  0  0
 22  3  1  0  0  0  0
 22 19  1  0  0  0  0
 23 12  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036459

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3

> <INCHI_KEY>
QDDILOVMGWUNGD-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.4022

> <EXACT_MASS>
328.167459256

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.12366002944521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[3-(2H-1,3-benzodioxol-5-ylmethyl)-2-methylbutyl]-2-methoxyphenol

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.134780911

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.275429206619169

> <JCHEM_PKA_STRONGEST_BASIC>
-4.506185107463003

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
92.90639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
macelignan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036459
     RDKit          3D
Macelignan
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8946    2.6778   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289    1.6262   -0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1020    0.5676    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    0.5377    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1079   -0.4862    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -0.4821    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893   -1.2101    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.7051    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734   -0.6646   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.4947   -1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645    0.6201   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.5385   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6183    0.1794   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952    0.1212   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444    0.4194    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    0.7777    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.8294    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026    1.0205    2.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059    1.1721    2.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2911    0.4484    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -1.5230    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2734   -1.5255    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8939   -0.4824    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2724   -0.4806    0.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.2839   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    3.4083   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677    3.1741   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942    1.4047   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    0.5599    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -0.9033    2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -1.2507    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084   -3.1750   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280   -2.7707   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -3.1854    1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9538   -1.4909   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625    0.5814   -2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.1725   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -0.7607   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391    1.0386   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    1.3604   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624   -0.0589   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.1613   -1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    1.1249    1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.6478    3.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998    2.2285    2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.3529    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323   -2.3224    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568    0.3104   -0.1594 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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.132  -0.476   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   22                                                            
CONECT    4    6   15                                                       
CONECT    5    7   16                                                       
CONECT    6    4   17                                                       
CONECT    7    5   18                                                       
CONECT    8   13   15                                                       
CONECT    9   14   16                                                       
CONECT   10   15   19                                                       
CONECT   11   16   20                                                       
CONECT   12   23   24                                                       
CONECT   13    1    8   14                                                  
CONECT   14    2    9   13                                                  
CONECT   15    4    8   10                                                  
CONECT   16    5    9   11                                                  
CONECT   17    6   19   21                                                  
CONECT   18    7   20   23                                                  
CONECT   19   10   17   22                                                  
CONECT   20   11   18   24                                                  
CONECT   21   17                                                            
CONECT   22    3   19                                                       
CONECT   23   12   18                                                       
CONECT   24   12   20                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0036459
HETATM    1  C1  UNL     1      -3.895   2.678  -1.026  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.729   1.626  -0.579  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.102   0.568   0.102  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.743   0.538   0.333  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.108  -0.486   0.996  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.652  -0.482   1.218  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.189  -1.210   0.253  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.170  -2.705   0.178  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.373  -0.665  -1.109  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.869  -0.495  -1.940  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.164   0.620  -1.187  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.533   0.539  -0.687  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.618   0.179  -1.478  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.895   0.121  -0.961  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.144   0.419   0.369  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.082   0.778   1.169  1.00  0.00           C  
HETATM   17  C16 UNL     1       2.807   0.829   0.627  1.00  0.00           C  
HETATM   18  O2  UNL     1       4.603   1.020   2.438  1.00  0.00           O  
HETATM   19  C17 UNL     1       6.006   1.172   2.335  1.00  0.00           C  
HETATM   20  O3  UNL     1       6.291   0.448   1.156  1.00  0.00           O  
HETATM   21  C18 UNL     1      -2.914  -1.523   1.439  1.00  0.00           C  
HETATM   22  C19 UNL     1      -4.273  -1.525   1.226  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.894  -0.482   0.555  1.00  0.00           C  
HETATM   24  O4  UNL     1      -6.272  -0.481   0.336  1.00  0.00           O  
HETATM   25  H1  UNL     1      -3.061   2.284  -1.678  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.429   3.408  -1.643  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.368   3.174  -0.166  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.194   1.405  -0.054  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.256   0.560   1.322  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.509  -0.903   2.262  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.244  -1.251   0.704  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.508  -3.175  -0.569  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.228  -2.771  -0.083  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.043  -3.185   1.172  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.954  -1.491  -1.666  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.162   0.581  -2.039  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.687  -1.173  -1.687  1.00  0.00           H  
HETATM   38  H14 UNL     1      -0.610  -0.761  -3.016  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.139   1.039  -2.213  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.612   1.360  -0.555  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.462  -0.059  -2.515  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.755  -0.161  -1.579  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.034   1.125   1.334  1.00  0.00           H  
HETATM   44  H20 UNL     1       6.489   0.648   3.193  1.00  0.00           H  
HETATM   45  H21 UNL     1       6.300   2.228   2.287  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.447  -2.353   1.969  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.932  -2.322   1.561  1.00  0.00           H  
HETATM   48  H24 UNL     1      -6.657   0.310  -0.159  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6   21   21
CONECT    6    7   29   30
CONECT    7    8    9   31
CONECT    8   32   33   34
CONECT    9   10   11   35
CONECT   10   36   37   38
CONECT   11   12   39   40
CONECT   12   13   13   17
CONECT   13   14   41
CONECT   14   15   15   42
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   17   43
CONECT   18   19
CONECT   19   20   44   45
CONECT   21   22   46
CONECT   22   23   23   47
CONECT   23   24
CONECT   24   48
END

HMDB0036459
     RDKit          3D
Macelignan
 48 50  0  0  0  0  0  0  0  0999 V2000
   -3.8946    2.6778   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289    1.6262   -0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1020    0.5676    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    0.5377    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1079   -0.4862    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6521   -0.4821    1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893   -1.2101    0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.7051    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3734   -0.6646   -1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -0.4947   -1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1645    0.6201   -1.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5333    0.5385   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6183    0.1794   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8952    0.1212   -0.9610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444    0.4194    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0822    0.7777    1.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065    0.8294    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6026    1.0205    2.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059    1.1721    2.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2911    0.4484    1.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9142   -1.5230    1.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2734   -1.5255    1.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8939   -0.4824    0.5545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2724   -0.4806    0.3362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606    2.2839   -1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4295    3.4083   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3677    3.1741   -0.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942    1.4047   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559    0.5599    1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -0.9033    2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439   -1.2507    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084   -3.1750   -0.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280   -2.7707   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0425   -3.1854    1.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9538   -1.4909   -1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625    0.5814   -2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6866   -1.1725   -1.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -0.7607   -3.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391    1.0386   -2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    1.3604   -0.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4624   -0.0589   -2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7547   -0.1613   -1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0344    1.1249    1.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.6478    3.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2998    2.2285    2.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4466   -2.3529    1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323   -2.3224    1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6568    0.3104   -0.1594 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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 12  1  0
 20 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 22 47  1  0
 24 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anwulignan	HMDB
Calophyn	HMDB

Chemical Formula

C₂₀H₂₄O₄

Average Molecular Weight

328.4022

Monoisotopic Molecular Weight

328.167459256

IUPAC Name

4-[3-(2H-1,3-benzodioxol-5-ylmethyl)-2-methylbutyl]-2-methoxyphenol

Traditional Name

macelignan

CAS Registry Number

107534-93-0

SMILES

COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1

InChI Identifier

InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3

InChI Key

QDDILOVMGWUNGD-UHFFFAOYSA-N

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
Methoxyphenol
Benzodioxole
Phenylpropane
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036459)

Cellular substructure

Membrane (HMDB: HMDB0036459)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036459)

Source

Exogenous

Food

Food (HMDB: HMDB0036459)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0036459)

Not Available

Nutrient (HMDB: HMDB0036459)

Industrial application

Pharmaceutical industry

Anti-inflammatory (HMDB: HMDB0036459)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	70 - 72 °C	Not Available
Boiling Point	467.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.067 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.220 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0028 g/L	ALOGPS
logP	4.86	ALOGPS
logP	5.13	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	180.193	31661259
DarkChem	[M-H]-	181.612	31661259
DeepCCS	[M+H]+	185.944	30932474
DeepCCS	[M-H]-	183.394	30932474
DeepCCS	[M-2H]-	218.084	30932474
DeepCCS	[M+Na]+	194.374	30932474
AllCCS	[M+H]+	180.7	32859911
AllCCS	[M+H-H2O]+	177.2	32859911
AllCCS	[M+NH4]+	183.8	32859911
AllCCS	[M+Na]+	184.7	32859911
AllCCS	[M-H]-	185.6	32859911
AllCCS	[M+Na-2H]-	185.5	32859911
AllCCS	[M+HCOO]-	185.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Macelignan	COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1	3497.0	Standard polar	33892256
Macelignan	COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1	2551.2	Standard non polar	33892256
Macelignan	COC1=C(O)C=CC(CC(C)C(C)CC2=CC3=C(OCO3)C=C2)=C1	2667.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Macelignan,1TMS,isomer #1	COC1=CC(CC(C)C(C)CC2=CC=C3OCOC3=C2)=CC=C1O[Si](C)(C)C	2731.6	Semi standard non polar	33892256
Macelignan,1TBDMS,isomer #1	COC1=CC(CC(C)C(C)CC2=CC=C3OCOC3=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3000.8	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 - Macelignan GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p9-0901000000-22bfca8f123cc67d052f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macelignan GC-MS (1 TMS) - 70eV, Positive	splash10-000i-1955000000-db8e56fb66b08c29ae2c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Macelignan 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 - Macelignan , positive-QTOF	splash10-000i-0900000000-d8bdc4c1e4a630ae1fe4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Macelignan , positive-QTOF	splash10-000i-0910000000-c90b1f74544adb5ae68d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOF	splash10-004i-0329000000-956206a54fffd039a221	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOF	splash10-08ic-1942000000-026059a678a1532f8b12	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOF	splash10-0i09-5921000000-e058d00c237d34bd5363	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOF	splash10-004i-0009000000-600c1a450b0ced22ebc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOF	splash10-004i-0039000000-7002ffddbbdf0a7f195c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOF	splash10-0bu0-1392000000-0f40cab6ee1e5be055f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 10V, Negative-QTOF	splash10-004i-0009000000-fd417bc7f7b273e09154	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 20V, Negative-QTOF	splash10-004i-0169000000-751be5e231bc8180cb86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 40V, Negative-QTOF	splash10-004i-0549000000-d0aaa2726ea7c14d5c05	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 10V, Positive-QTOF	splash10-004j-0296000000-78591524d90c87ba316b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 20V, Positive-QTOF	splash10-052u-0941000000-dccc0af62bd2f1f9ee0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Macelignan 40V, Positive-QTOF	splash10-0570-0972000000-b1112c488d3d6031c069	2021-09-22	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

Not Available

FooDB ID

FDB015348

KNApSAcK ID

C00031992

Chemspider ID

22370206

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Macelignan

METLIN ID

Not Available

PubChem Compound

13844304

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1684861

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sohn JH, Han KL, Kim JH, Rukayadi Y, Hwang JK: Protective Effects of macelignan on cisplatin-induced hepatotoxicity is associated with JNK activation. Biol Pharm Bull. 2008 Feb;31(2):273-7. [PubMed:18239286 ]
Ma J, Hwang YK, Cho WH, Han SH, Hwang JK, Han JS: Macelignan attenuates activations of mitogen-activated protein kinases and nuclear factor kappa B induced by lipopolysaccharide in microglial cells. Biol Pharm Bull. 2009 Jun;32(6):1085-90. [PubMed:19483320 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Macelignan (HMDB0036459)

MOL for HMDB0036459 (Macelignan)

3D MOL for HMDB0036459 (Macelignan)

3D SDF for HMDB0036459 (Macelignan)

3D-SDF for HMDB0036459 (Macelignan)

PDB for HMDB0036459 (Macelignan)

3D PDB for HMDB0036459 (Macelignan)

SMILES for HMDB0036459 (Macelignan)

INCHI for HMDB0036459 (Macelignan)

Structure for HMDB0036459 (Macelignan)

3D Structure for HMDB0036459 (Macelignan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra