NP-MRD: Showing NP-Card for 5,5'-Dimethoxylariciresinol (NP0137698)

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Record Information

Version

2.0

Created at

2022-05-31 16:03:54 UTC

Updated at

2022-05-31 16:03:54 UTC

NP-MRD ID

NP0137698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5'-Dimethoxylariciresinol

Description

(+)-(7S,8R,8'R)-5,5'-dimethoxylariciresinol belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (+)-(7S,8R,8'R)-5,5'-dimethoxylariciresinol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 5,5'-Dimethoxylariciresinol is found in Annona squamosa, Bambusa emeiensis, Campylotropis hirtella and Parthenium hysterophorus. 5,5'-Dimethoxylariciresinol was first documented in 2007 (PMID: 17958322). Based on a literature review very few articles have been published on (+)-(7S,8R,8'R)-5,5'-dimethoxylariciresinol (PMID: 24014307).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218032D          

 33 35  0  0  1  0            999 V2000
   -0.0206   -0.8630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  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
    1.4289   -0.0000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5129   -2.3780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -5.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -3.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8317   -1.9774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  4 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
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 17 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    4.9095   -1.9093    2.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -0.7774    1.6088 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7282   -0.2386    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5303   -0.7841    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040   -0.2834   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5466   -0.8747   -1.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2632   -0.2195   -1.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8258   -1.1423   -1.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2503   -1.9034   -0.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.0740    0.3838 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6987   -0.5058    0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344    0.7401    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3864    1.1072    0.9965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7008    2.3676    1.4376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    3.2768    1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3887    0.2352    0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7359    0.6273    0.6643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0596   -1.0286    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0798   -1.9029   -0.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6921   -3.1889   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.3730    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2271   -0.1037    0.2467 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7625   -0.2551    1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0504   -0.0821    2.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3381    0.8416   -1.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143    1.3912   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0619    2.5134   -1.7754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4518    3.1575   -2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2393    0.8691   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4218    1.4315    0.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6393   -2.2385    3.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -2.7679    1.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9622   -1.6407    2.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2313   -1.6797    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -1.0730   -2.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5550   -1.9532   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    0.7631   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -0.4878   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642   -1.7404   -2.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -1.7285    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726    1.4354    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0465    3.5685    0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2125    4.2110    2.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1030    2.8101    2.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4475   -0.0156    0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0378   -3.6990    0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -3.0159   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5661   -3.8495   -0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5147   -2.3830   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679    0.9738    0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    0.5635    1.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325   -1.2850    1.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2887    0.8600    2.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.2526   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    3.8067   -2.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2357    3.7741   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710    2.3828   -3.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8414    2.2445   -0.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 29  2  0
 29 30  1  0
 29 26  1  0
 26 27  1  0
 27 28  1  0
 26 25  2  0
  7  8  1  0
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  9 10  1  0
 10 11  1  0
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 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 22  7  1  0
 25  5  1  0
 21 11  1  0
  7 37  1  6
  6 35  1  0
  6 36  1  0
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  1 33  1  0
 30 58  1  0
 28 55  1  0
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 25 54  1  0
  8 38  1  0
  8 39  1  0
 10 40  1  1
 12 41  1  0
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 17 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 22 50  1  6
 23 51  1  0
 23 52  1  0
 24 53  1  0
M  END


  Mrv1652305312218032D          

 33 35  0  0  1  0            999 V2000
   -0.0206   -0.8630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  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
    1.4289   -0.0000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5129   -2.3780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -5.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -5.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -5.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -3.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6444   -2.9158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8317   -1.9774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -0.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
  4 14  1  0  0  0  0
  2 15  1  0  0  0  0
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 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 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
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
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 17 30  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0137698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC2=CC(OC)=C(O)C(OC)=C2)CO[C@]([H])(C2=CC(OC)=C(O)C(OC)=C2)[C@@]1([H])CO

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-26-16-6-12(7-17(27-2)20(16)24)5-14-11-30-22(15(14)10-23)13-8-18(28-3)21(25)19(9-13)29-4/h6-9,14-15,22-25H,5,10-11H2,1-4H3/t14-,15-,22+/m0/s1

> <INCHI_KEY>
HBBWYJVDBFYNOP-AYSMAOOMSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.413451436322305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2,6-dimethoxyphenol

> <JCHEM_LOGP>
1.989967783666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.831104301183219

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.15031885247117

> <JCHEM_PKA_STRONGEST_BASIC>
-2.639333518647569

> <JCHEM_POLAR_SURFACE_AREA>
106.84000000000002

> <JCHEM_REFRACTIVITY>
110.12000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3R,4R)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2,6-dimethoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -0.038  -1.611   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104  -4.680   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -0.957  -4.439   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.006  -9.985   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.538 -10.146   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.057  -9.663   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.310  -6.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.936  -5.443   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.552  -3.691   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.697  -1.233   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15   30                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    4                                                       
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   19                                                       
CONECT   30   17    2   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

116498-58-9

SMILES

[H][C@]1(CC2=CC(OC)=C(O)C(OC)=C2)CO[C@]([H])(C2=CC(OC)=C(O)C(OC)=C2)[C@@]1([H])CO

InChI Identifier

InChI=1S/C22H28O8/c1-26-16-6-12(7-17(27-2)20(16)24)5-14-11-30-22(15(14)10-23)13-8-18(28-3)21(25)19(9-13)29-4/h6-9,14-15,22-25H,5,10-11H2,1-4H3/t14-,15-,22+/m0/s1

InChI Key

HBBWYJVDBFYNOP-AYSMAOOMSA-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
Annona squamosa	LOTUS Database	35616633
Bambusa emeiensis	LOTUS Database	35616633
Campylotropis hirtella	LOTUS Database	35616633
Parthenium hysterophorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:67650 )
primary alcohol (CHEBI:67650 )
dimethoxybenzene (CHEBI:67650 )
oxolanes (CHEBI:67650 )
lignan (CHEBI:67650 )

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

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

28283025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14157882

PDB ID

Not Available

ChEBI ID

67650

Good Scents ID

Not Available

References

General References

Yang MC, Lee KH, Kim KH, Choi SU, Lee KR: Lignan and terpene constituents from the aerial parts of Saussurea pulchella. Arch Pharm Res. 2007 Sep;30(9):1067-74. doi: 10.1007/BF02980239. [PubMed:17958322 ]
Choi HG, Choi YH, Kim JH, Kim HH, Kim SH, Kim JA, Lee SM, Na M, Lee SH: A new neolignan and lignans from the stems of Lindera obtusiloba Blume and their anti-allergic inflammatory effects. Arch Pharm Res. 2014 Apr;37(4):467-72. doi: 10.1007/s12272-013-0239-7. Epub 2013 Sep 8. [PubMed:24014307 ]

Showing NP-Card for 5,5'-Dimethoxylariciresinol (NP0137698)

MOL for NP0137698 (5,5'-Dimethoxylariciresinol)

3D MOL for NP0137698 (5,5'-Dimethoxylariciresinol)

3D SDF for NP0137698 (5,5'-Dimethoxylariciresinol)

3D-SDF for NP0137698 (5,5'-Dimethoxylariciresinol)

PDB for NP0137698 (5,5'-Dimethoxylariciresinol)

3D PDB for NP0137698 (5,5'-Dimethoxylariciresinol)

SMILES for NP0137698 (5,5'-Dimethoxylariciresinol)

INCHI for NP0137698 (5,5'-Dimethoxylariciresinol)

Structure for NP0137698 (5,5'-Dimethoxylariciresinol)

3D Structure for NP0137698 (5,5'-Dimethoxylariciresinol)