NP-MRD: Showing NP-Card for {4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate (NP0182653)

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Record Information

Version

1.0

Created at

2022-09-03 21:24:04 UTC

Updated at

2022-09-03 21:24:05 UTC

NP-MRD ID

NP0182653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

Description

{4-[(Acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). {4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate is found in Pleione bulbocodioides. {4-[(Acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508122D          

 33 35  0  0  0  0            999 V2000
   -0.1067    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 O   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
    2.7512   -0.0616    0.0000 O   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    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    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
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    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
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580   -1.0192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6164    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9411   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719   -4.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -4.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -4.8666   -1.3976    2.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7230   -0.0617    3.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7397    0.7076    2.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9260    0.2597    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9369    1.0577    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1464    0.4305    0.0866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1788   -0.2346   -0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -1.5838   -0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4102   -2.1224   -1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376   -2.3267   -0.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469    1.2908   -0.8753 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5804    2.2567   -0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6361    2.1688   -1.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9857    1.7557   -2.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2304    0.5442   -2.0058 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1982   -0.5008   -1.6814 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7220   -1.1316   -2.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4923   -2.4920   -2.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -3.2892   -4.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -3.1460   -2.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -0.1480   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362    0.3078   -1.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    0.6334   -0.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8415    0.5143    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243    0.8367    1.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255    0.0567    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8195   -0.0753    2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7759   -0.5243    3.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.2739    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7505    2.3242    1.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5745    2.8002    2.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5377    2.0041    3.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3646    2.4678    4.2238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.9907    3.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0437   -1.3759    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7575   -1.8251    3.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0983   -0.7566    1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5643   -0.4438    0.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383   -1.4473   -2.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -3.1375   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3810   -2.1357   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2427    1.9227   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2679    3.3371   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    2.0669    0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2565    2.5236   -2.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6378    1.5412   -3.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    0.2127   -2.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949   -1.2720   -1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0245   -3.5849   -3.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9549   -2.6633   -5.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671   -4.2115   -4.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4903    0.4017   -2.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    0.9956   -1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7973    1.1648    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9657    0.2227    3.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012   -0.8278    4.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449   -1.4350    2.7823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6847   -0.6404    1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    3.0186    1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310    3.8113    2.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2106    3.4195    4.5271 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 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
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 17 18  1  0
 18 19  1  0
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 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 32  3  1  0
 15 11  1  0
 29 21  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
 30 59  1  0
 31 60  1  0
 33 61  1  0
  6 38  1  1
  9 39  1  0
  9 40  1  0
  9 41  1  0
 11 42  1  6
 12 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  6
 16 48  1  1
 19 49  1  0
 19 50  1  0
 19 51  1  0
 22 52  1  0
 23 53  1  0
 25 54  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 29 58  1  0
M  END


  Mrv1533004161508122D          

 33 35  0  0  0  0            999 V2000
   -0.1067    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 O   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
    2.7512   -0.0616    0.0000 O   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    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    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
    1.6242   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    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
    3.4888   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6603   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0580   -1.0192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6164    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9411   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3719   -4.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -4.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9303   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
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 12 13  2  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
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 25 26  2  0  0  0  0
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 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(OC(C)=O)C1COCC1C(OC(C)=O)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O9/c1-13(25)32-23(15-5-7-19(27)21(9-15)29-3)17-11-31-12-18(17)24(33-14(2)26)16-6-8-20(28)22(10-16)30-4/h5-10,17-18,23-24,27-28H,11-12H2,1-4H3

> <INCHI_KEY>
XTVMVCMAKJEEEJ-UHFFFAOYSA-N

> <FORMULA>
C24H28O9

> <MOLECULAR_WEIGHT>
460.479

> <EXACT_MASS>
460.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
46.43749736164739

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
1.9983067956666665

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.211209902294444

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.609149910966488

> <JCHEM_PKA_STRONGEST_BASIC>
-3.999271523851944

> <JCHEM_POLAR_SURFACE_AREA>
120.75

> <JCHEM_REFRACTIVITY>
116.9133

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.199   4.505   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.134   3.735   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.199  -0.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.533   2.195   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.136  -0.115   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.469   2.195   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.833  -1.348   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.297  -0.872   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.442  -1.903   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.617   0.634   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.121  -3.409   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.266  -4.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.946  -5.946   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.090  -6.976   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.481  -6.422   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.161  -7.928   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.696  -8.404   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.337  -5.391   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   25                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₈O₉

Average Mass

460.4790 Da

Monoisotopic Mass

460.17333 Da

IUPAC Name

{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

Traditional Name

{4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(OC(C)=O)C1COCC1C(OC(C)=O)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C24H28O9/c1-13(25)32-23(15-5-7-19(27)21(9-15)29-3)17-11-31-12-18(17)24(33-14(2)26)16-6-8-20(28)22(10-16)30-4/h5-10,17-18,23-24,27-28H,11-12H2,1-4H3

InChI Key

XTVMVCMAKJEEEJ-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
Pleione bulbocodioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

9,9'-epoxylignans

Alternative Parents

Substituents

9,9p-epoxylignan
Benzyloxycarbonyl
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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	2.59	ALOGPS
logP	2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.75 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	116.91 m³·mol⁻¹	ChemAxon
Polarizability	46.44 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate (NP0182653)

MOL for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

3D MOL for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

3D SDF for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

3D-SDF for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

PDB for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

3D PDB for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

SMILES for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

INCHI for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

Structure for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)

3D Structure for NP0182653 ({4-[(acetyloxy)(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl}(4-hydroxy-3-methoxyphenyl)methyl acetate)