NP-MRD: Showing NP-Card for (+-)-3',3''-bisdemethylpinoresinol (NP0030682)

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Record Information

Version

2.0

Created at

2021-06-19 21:58:18 UTC

Updated at

2021-06-29 23:58:48 UTC

NP-MRD ID

NP0030682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+-)-3',3''-bisdemethylpinoresinol

Provided By

JEOL Database JEOL Logo

Description

(+)-Sesamin dicatechol is also known as SC-2 (+)-sesamin dicatechol 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. (+-)-3',3''-bisdemethylpinoresinol is found in Joannesia princeps and Morinda citrifolia. (+-)-3',3''-bisdemethylpinoresinol was first documented in 2006 (PMID: 16597711). Based on a literature review a small amount of articles have been published on (+)-sesamin dicatechol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123583D          

 42 45  0  0  0  0            999 V2000
   -2.0424   -2.8080   -6.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -2.4593   -5.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2888   -2.9127   -5.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -2.5181   -3.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -1.6773   -2.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -1.2185   -1.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.1388   -1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -1.4094   -0.6970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6852    0.0442   -0.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9624    0.4318    0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8735    1.1473    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.3944    2.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.0241    3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.4079    3.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.0248    4.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    3.1687    2.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    4.5304    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    2.5504    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    1.2709    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    1.2903   -1.1406 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5999    0.1534   -1.6557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8324   -1.2315   -3.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.6241   -4.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.1783   -5.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -3.4108   -7.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -3.5665   -5.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -2.8791   -3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178   -1.2298   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -1.8071    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157   -1.5719   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.7112   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.4374    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -0.6928    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.4407    4.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    3.9794    4.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    4.9147    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.1439    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    1.2285   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    2.2541   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956    0.3582   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.5851   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.5884   -5.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  5 22  2  0  0  0  0
  8  9  1  0  0  0  0
 22 23  1  0  0  0  0
  9 10  1  0  0  0  0
 23  2  2  0  0  0  0
 10 19  1  0  0  0  0
  2  3  1  0  0  0  0
 19 20  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 20 21  1  0  0  0  0
  2  1  1  0  0  0  0
 21  9  1  0  0  0  0
 23 24  1  0  0  0  0
 21 40  1  6  0  0  0
 16 14  2  0  0  0  0
  9 31  1  6  0  0  0
 14 13  1  0  0  0  0
 21  6  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
  6  5  1  0  0  0  0
 11 18  2  0  0  0  0
 18 16  1  0  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  1  0  0  0  0
  6 28  1  1  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 10 32  1  1  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 22 41  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  1 25  1  0  0  0  0
 24 42  1  0  0  0  0
 13 34  1  0  0  0  0
 12 33  1  0  0  0  0
 18 37  1  0  0  0  0
 17 36  1  0  0  0  0
 15 35  1  0  0  0  0
M  END

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.0424   -2.8080   -6.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -2.4593   -5.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2888   -2.9127   -5.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -2.5181   -3.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -1.6773   -2.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -1.2185   -1.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.1388   -1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -1.4094   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    0.0442   -0.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9624    0.4318    0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8735    1.1473    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.3944    2.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.0241    3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.4079    3.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.0248    4.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    3.1687    2.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    4.5304    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    2.5504    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    1.2709    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    1.2903   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999    0.1534   -1.6557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8324   -1.2315   -3.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.6241   -4.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.1783   -5.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -3.4108   -7.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -3.5665   -5.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -2.8791   -3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178   -1.2298   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -1.8071    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157   -1.5719   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.7112   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.4374    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -0.6928    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.4407    4.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    3.9794    4.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    4.9147    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.1439    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    1.2285   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    2.2541   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956    0.3582   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.5851   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.5884   -5.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  5 22  2  0
  8  9  1  0
 22 23  1  0
  9 10  1  0
 23  2  2  0
 10 19  1  0
  2  3  1  0
 19 20  1  0
  3  4  2  0
  4  5  1  0
 20 21  1  0
  2  1  1  0
 21  9  1  0
 23 24  1  0
 21 40  1  6
 16 14  2  0
  9 31  1  6
 14 13  1  0
 21  6  1  0
 13 12  2  0
 12 11  1  0
  6  5  1  0
 11 18  2  0
 18 16  1  0
  6  7  1  0
 16 17  1  0
 10 11  1  0
 14 15  1  0
  6 28  1  1
  8 29  1  0
  8 30  1  0
 10 32  1  1
 20 38  1  0
 20 39  1  0
 22 41  1  0
  3 26  1  0
  4 27  1  0
  1 25  1  0
 24 42  1  0
 13 34  1  0
 12 33  1  0
 18 37  1  0
 17 36  1  0
 15 35  1  0
M  END


  Mrv1652306192123583D          

 42 45  0  0  0  0            999 V2000
   -2.0424   -2.8080   -6.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -2.4593   -5.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2888   -2.9127   -5.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -2.5181   -3.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -1.6773   -2.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -1.2185   -1.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.1388   -1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -1.4094   -0.6970 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6852    0.0442   -0.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9624    0.4318    0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8735    1.1473    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.3944    2.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.0241    3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.4079    3.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.0248    4.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    3.1687    2.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    4.5304    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    2.5504    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    1.2709    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    1.2903   -1.1406 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5999    0.1534   -1.6557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8324   -1.2315   -3.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.6241   -4.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.1783   -5.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -3.4108   -7.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -3.5665   -5.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -2.8791   -3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178   -1.2298   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -1.8071    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157   -1.5719   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.7112   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.4374    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -0.6928    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.4407    4.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    3.9794    4.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    4.9147    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.1439    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    1.2285   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    2.2541   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956    0.3582   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.5851   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.5884   -5.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  5 22  2  0  0  0  0
  8  9  1  0  0  0  0
 22 23  1  0  0  0  0
  9 10  1  0  0  0  0
 23  2  2  0  0  0  0
 10 19  1  0  0  0  0
  2  3  1  0  0  0  0
 19 20  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
 20 21  1  0  0  0  0
  2  1  1  0  0  0  0
 21  9  1  0  0  0  0
 23 24  1  0  0  0  0
 21 40  1  6  0  0  0
 16 14  2  0  0  0  0
  9 31  1  6  0  0  0
 14 13  1  0  0  0  0
 21  6  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
  6  5  1  0  0  0  0
 11 18  2  0  0  0  0
 18 16  1  0  0  0  0
  6  7  1  0  0  0  0
 16 17  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  1  0  0  0  0
  6 28  1  1  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 10 32  1  1  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 22 41  1  0  0  0  0
  3 26  1  0  0  0  0
  4 27  1  0  0  0  0
  1 25  1  0  0  0  0
 24 42  1  0  0  0  0
 13 34  1  0  0  0  0
 12 33  1  0  0  0  0
 18 37  1  0  0  0  0
 17 36  1  0  0  0  0
 15 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2([H])[C@]([H])(OC([H])([H])[C@]12[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1

> <INCHI_KEY>
OQSOTSIYXPYTRE-YDOWWZDFSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.955535069643204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.9859714353333329

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.514458571087857

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.912705571952898

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8805422004257433

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
86.13560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.0424   -2.8080   -6.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -2.4593   -5.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2888   -2.9127   -5.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -2.5181   -3.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -1.6773   -2.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -1.2185   -1.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.1388   -1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -1.4094   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    0.0442   -0.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9624    0.4318    0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8735    1.1473    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.3944    2.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.0241    3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.4079    3.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.0248    4.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    3.1687    2.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    4.5304    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    2.5504    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    1.2709    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    1.2903   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999    0.1534   -1.6557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8324   -1.2315   -3.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.6241   -4.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.1783   -5.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -3.4108   -7.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -3.5665   -5.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -2.8791   -3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178   -1.2298   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -1.8071    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157   -1.5719   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.7112   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.4374    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -0.6928    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.4407    4.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    3.9794    4.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    4.9147    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.1439    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    1.2285   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    2.2541   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956    0.3582   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.5851   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.5884   -5.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  5 22  2  0
  8  9  1  0
 22 23  1  0
  9 10  1  0
 23  2  2  0
 10 19  1  0
  2  3  1  0
 19 20  1  0
  3  4  2  0
  4  5  1  0
 20 21  1  0
  2  1  1  0
 21  9  1  0
 23 24  1  0
 21 40  1  6
 16 14  2  0
  9 31  1  6
 14 13  1  0
 21  6  1  0
 13 12  2  0
 12 11  1  0
  6  5  1  0
 11 18  2  0
 18 16  1  0
  6  7  1  0
 16 17  1  0
 10 11  1  0
 14 15  1  0
  6 28  1  1
  8 29  1  0
  8 30  1  0
 10 32  1  1
 20 38  1  0
 20 39  1  0
 22 41  1  0
  3 26  1  0
  4 27  1  0
  1 25  1  0
 24 42  1  0
 13 34  1  0
 12 33  1  0
 18 37  1  0
 17 36  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.042  -2.808  -6.677  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.528  -2.459  -5.459  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.289  -2.913  -5.028  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.182  -2.518  -3.770  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.582  -1.677  -2.939  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.079  -1.218  -1.587  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.899  -2.139  -1.054  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.079  -1.409  -0.697  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.685   0.044  -0.620  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.962   0.432   0.673  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.874   1.147   1.649  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.687   0.394   2.518  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.560   1.024   3.408  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.620   2.408   3.432  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.473   3.025   4.301  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.821   3.169   2.584  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.923   4.530   2.666  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.952   2.550   1.691  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.149   1.271   0.289  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.247   1.290  -1.141  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.600   0.153  -1.656  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.832  -1.232  -3.398  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.290  -1.624  -4.649  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.506  -1.178  -5.081  0.00  0.00           O+0
HETATM   25  H   UNK     0      -1.412  -3.411  -7.108  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.322  -3.567  -5.641  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.152  -2.879  -3.435  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.918  -1.230  -0.879  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.488  -1.807   0.236  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.816  -1.572  -1.492  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.530   0.711  -0.827  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.521  -0.437   1.178  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.641  -0.693   2.513  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.184   0.441   4.078  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.332   3.979   4.142  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.257   4.915   2.069  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.328   3.144   1.029  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.298   1.228  -1.436  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.148   2.254  -1.480  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.996   0.358  -2.657  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.457  -0.585  -2.788  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.616  -1.588  -5.962  0.00  0.00           H+0
CONECT    1    2   25                                                       
CONECT    2   23    3    1                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   27                                                  
CONECT    5   22    4    6                                                  
CONECT    6   21    5    7   28                                             
CONECT    7    8    6                                                       
CONECT    8    7    9   29   30                                             
CONECT    9    8   10   21   31                                             
CONECT   10    9   19   11   32                                             
CONECT   11   12   18   10                                                  
CONECT   12   13   11   33                                                  
CONECT   13   14   12   34                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   35                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   36                                                       
CONECT   18   11   16   37                                                  
CONECT   19   10   20                                                       
CONECT   20   19   21   38   39                                             
CONECT   21   20    9   40    6                                             
CONECT   22    5   23   41                                                  
CONECT   23   22    2   24                                                  
CONECT   24   23   42                                                       
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   24                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

RDKit          3D

42 45  0  0  0  0  0  0  0  0999 V2000
   -2.0424   -2.8080   -6.6772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5276   -2.4593   -5.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2888   -2.9127   -5.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1816   -2.5181   -3.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823   -1.6773   -2.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793   -1.2185   -1.5870 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.1388   -1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791   -1.4094   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6852    0.0442   -0.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9624    0.4318    0.6733 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8735    1.1473    1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    0.3944    2.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5603    1.0241    3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    2.4079    3.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4733    3.0248    4.3009 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    3.1687    2.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9228    4.5304    2.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9517    2.5504    1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486    1.2709    0.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473    1.2903   -1.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999    0.1534   -1.6557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8324   -1.2315   -3.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2898   -1.6241   -4.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062   -1.1783   -5.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -3.4108   -7.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3219   -3.5665   -5.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -2.8791   -3.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9178   -1.2298   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4876   -1.8071    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8157   -1.5719   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.7112   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5212   -0.4374    1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6413   -0.6928    2.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.4407    4.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3323    3.9794    4.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2572    4.9147    2.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284    3.1439    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980    1.2285   -1.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    2.2541   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956    0.3582   -2.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568   -0.5851   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.5884   -5.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  5 22  2  0
  8  9  1  0
 22 23  1  0
  9 10  1  0
 23  2  2  0
 10 19  1  0
  2  3  1  0
 19 20  1  0
  3  4  2  0
  4  5  1  0
 20 21  1  0
  2  1  1  0
 21  9  1  0
 23 24  1  0
 21 40  1  6
 16 14  2  0
  9 31  1  6
 14 13  1  0
 21  6  1  0
 13 12  2  0
 12 11  1  0
  6  5  1  0
 11 18  2  0
 18 16  1  0
  6  7  1  0
 16 17  1  0
 10 11  1  0
 14 15  1  0
  6 28  1  1
  8 29  1  0
  8 30  1  0
 10 32  1  1
 20 38  1  0
 20 39  1  0
 22 41  1  0
  3 26  1  0
  4 27  1  0
  1 25  1  0
 24 42  1  0
 13 34  1  0
 12 33  1  0
 18 37  1  0
 17 36  1  0
 15 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
SC-2	ChEBI

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol

Traditional Name

4-[(1S,3aR,4S,6aR)-4-(3,4-dihydroxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2([H])[C@]([H])(OC([H])([H])[C@]12[H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C18H18O6/c19-13-3-1-9(5-15(13)21)17-11-7-24-18(12(11)8-23-17)10-2-4-14(20)16(22)6-10/h1-6,11-12,17-22H,7-8H2/t11-,12-,17+,18+/m0/s1

InChI Key

OQSOTSIYXPYTRE-YDOWWZDFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 360 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 360 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Joannesia princeps	JEOL database	Waibel, R., et al., Phytochemistry 62, 805 (2003)
Morinda citrifolia	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.81	ALOGPS
logP	1.99	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.14 m³·mol⁻¹	ChemAxon
Polarizability	33.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24674520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

136543

Good Scents ID

Not Available

References

General References

Nakano D, Kwak CJ, Fujii K, Ikemura K, Satake A, Ohkita M, Takaoka M, Ono Y, Nakai M, Tomimori N, Kiso Y, Matsumura Y: Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin. J Pharmacol Exp Ther. 2006 Jul;318(1):328-35. doi: 10.1124/jpet.105.100149. Epub 2006 Apr 5. [PubMed:16597711 ]
Waibel, R., et al. (2003). Waibel, R., et al., Phytochemistry 62, 805 (2003). Phytochem..

Showing NP-Card for (+-)-3',3''-bisdemethylpinoresinol (NP0030682)

MOL for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

3D MOL for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

3D SDF for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

3D-SDF for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

PDB for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

3D PDB for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

SMILES for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

INCHI for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

Structure for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )

3D Structure for NP0030682 ( (+-)-3',3''-bisdemethylpinoresinol )