NP-MRD: Showing NP-Card for 3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol (NP0220071)

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Record Information

Version

2.0

Created at

2022-09-05 21:16:41 UTC

Updated at

2022-09-05 21:16:41 UTC

NP-MRD ID

NP0220071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol

Description

Cubebinin belongs to the class of organic compounds known as dibenzylbutyrolactols. These are lignan compounds containing a 3,4-dibenzyloxolan-2-ol moiety. Cubebinin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cubebinin has been detected, but not quantified in, herbs and spices. 3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol is found in Piper cubeba and Piper guineense. This could make cubebinin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307012D          

 32 34  0  0  0  0            999 V2000
    4.1801    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4992    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    1.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8861    1.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    0.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14  7  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 25 24  1  0  0  0  0
 26  1  1  0  0  0  0
 26 18  1  0  0  0  0
 27  2  1  0  0  0  0
 27 19  1  0  0  0  0
 28  3  1  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 21  1  0  0  0  0
 30  5  1  0  0  0  0
 30 22  1  0  0  0  0
 31  6  1  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
    2.9088    3.6449    1.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    2.6511    1.2222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688    1.3462    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661    1.0148    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9299   -0.2631    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5540   -0.6244   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040   -0.6303   -1.7327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7462   -0.9866   -2.4467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9023   -0.0881   -2.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7557    0.0113   -1.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6326    0.9863   -0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4228    1.0871    0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2493    2.1000    1.7207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    3.0452    1.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4113    0.1256    0.9528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2101    0.2301    2.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8823   -0.3987    3.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952   -0.8880    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6059   -1.7985    0.2833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9055   -2.8831   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7738   -0.9243   -1.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.8174   -3.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4117    0.4400   -3.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9034    0.6134   -2.4745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3944    1.7924   -1.9470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.2641    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904   -0.9909    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604   -1.9794    0.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -3.3183    0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782    0.3119    0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7713    0.6301    1.3278 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1662    0.5865    2.6884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988    3.6528    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    4.6625    1.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006    3.4753    1.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369    1.7881    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1048    0.0824    0.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3872   -1.6817    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -1.4067   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0316   -2.0589   -2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5318   -0.3995   -3.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    0.9438   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8617    1.7662   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093    3.8370    2.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2218    2.5830    1.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402    3.5639    0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7031   -1.0435    3.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7572    0.4158    4.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081   -0.9240    3.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8980   -3.2698   -0.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1896   -3.7265   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0140   -2.5603   -1.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9019   -1.7065   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6124   -1.6263   -4.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426   -0.8454   -4.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0099    0.7261   -2.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575    2.5312   -2.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346   -2.2838   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8022   -3.3951   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -3.6312    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7924   -3.9296    0.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4963   -0.0576    3.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2156    1.6017    3.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1865    0.1553    2.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24  7  1  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 30  2  0
 30 31  1  0
 31 32  1  0
 30 27  1  0
 27 28  1  0
 28 29  1  0
 27 26  2  0
 10 21  2  0
 21 18  1  0
 18 19  1  0
 19 20  1  0
 18 15  2  0
 15 16  1  0
 16 17  1  0
 15 12  1  0
  7  8  1  0
 26  5  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
 11 43  1  0
  9 41  1  0
  9 42  1  0
  8 40  1  1
 22 54  1  0
 22 55  1  0
 24 56  1  6
 25 57  1  0
  7 39  1  6
  6 37  1  0
  6 38  1  0
  4 36  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 26 58  1  0
 21 53  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
M  END


  Mrv0541 05061307012D          

 32 34  0  0  0  0            999 V2000
    4.1801    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4992    1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2963    1.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8861    1.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3277    0.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14  7  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 18  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 25 24  1  0  0  0  0
 26  1  1  0  0  0  0
 26 18  1  0  0  0  0
 27  2  1  0  0  0  0
 27 19  1  0  0  0  0
 28  3  1  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 21  1  0  0  0  0
 30  5  1  0  0  0  0
 30 22  1  0  0  0  0
 31  6  1  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC2COC(O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-26-18-9-14(10-19(27-2)22(18)30-5)7-16-13-32-24(25)17(16)8-15-11-20(28-3)23(31-6)21(12-15)29-4/h9-12,16-17,24-25H,7-8,13H2,1-6H3

> <INCHI_KEY>
PIYHDSUVUSVLGU-UHFFFAOYSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.5061

> <EXACT_MASS>
448.209718

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
47.29786120904825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.9924355609999997

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.16554585347608

> <JCHEM_PKA_STRONGEST_BASIC>
-3.920608968709248

> <JCHEM_POLAR_SURFACE_AREA>
84.84000000000002

> <JCHEM_REFRACTIVITY>
118.75299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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       7.803   4.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.470  -0.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.799   2.617   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.420   3.726   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.470   1.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.654   3.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.916  -0.318   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.127  -6.041   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.469   3.735   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.137  -0.885   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.478   1.110   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.740   2.219   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.572  -4.795   0.000  0.00  0.00           O+0
CONECT    1   26                                                            
CONECT    2   27                                                            
CONECT    3   28                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   14   16                                                       
CONECT    8   15   17                                                       
CONECT    9   14   18                                                       
CONECT   10   14   19                                                       
CONECT   11   15   20                                                       
CONECT   12   15   21                                                       
CONECT   13   16   32                                                       
CONECT   14    7    9   10                                                  
CONECT   15    8   11   12                                                  
CONECT   16    7   13   17                                                  
CONECT   17    8   16   24                                                  
CONECT   18    9   22   26                                                  
CONECT   19   10   22   27                                                  
CONECT   20   11   23   28                                                  
CONECT   21   12   23   29                                                  
CONECT   22   18   19   30                                                  
CONECT   23   20   21   31                                                  
CONECT   24   17   25   32                                                  
CONECT   25   24                                                            
CONECT   26    1   18                                                       
CONECT   27    2   19                                                       
CONECT   28    3   20                                                       
CONECT   29    4   21                                                       
CONECT   30    5   22                                                       
CONECT   31    6   23                                                       
CONECT   32   13   24                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxy-3,3',4,4',5,5'-hexamethoxy-9,9'-epoxylignan	HMDB
Tetrahydro-3,4-bis[(3,4,5-trimethoxyphenyl)methyl]-2-furanol, 9ci	HMDB

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5061 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol

Traditional Name

3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(CC2COC(O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C24H32O8/c1-26-18-9-14(10-19(27-2)22(18)30-5)7-16-13-32-24(25)17(16)8-15-11-20(28-3)23(31-6)21(12-15)29-4/h9-12,16-17,24-25H,7-8,13H2,1-6H3

InChI Key

PIYHDSUVUSVLGU-UHFFFAOYSA-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
Piper cubeba	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactols. These are lignan compounds containing a 3,4-dibenzyloxolan-2-ol moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactols

Alternative Parents

Substituents

Dibenzylbutyrolactol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Hemiacetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.03	ALOGPS
logP	2.99	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.84 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.75 m³·mol⁻¹	ChemAxon
Polarizability	47.3 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0033273

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011296

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75048911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol (NP0220071)

MOL for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

3D MOL for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

3D SDF for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

3D-SDF for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

PDB for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

3D PDB for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

SMILES for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

INCHI for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

Structure for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)

3D Structure for NP0220071 (3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-ol)