NP-MRD: Showing NP-Card for methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate (NP0154074)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 10:50:16 UTC

Updated at

2022-09-02 10:50:16 UTC

NP-MRD ID

NP0154074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate

Description

Methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadecan]-2,2'(7'),3',5,5',10'(15'),11',13'-octaene-1'-carboxylate belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton. methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate is found in Hopea reticulata. Methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]Hexadecan]-2,2'(7'),3',5,5',10'(15'),11',13'-octaene-1'-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506032D          

 38 43  0  0  0  0            999 V2000
    1.9950    1.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174    0.7809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -0.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5565   -0.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -2.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571   -1.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4434   -3.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3972   -1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7928   -1.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0428   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656    0.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025   -2.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980   -4.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8110   -5.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155   -3.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883   -1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855   -1.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -0.5093    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  5 24  1  0  0  0  0
 17 24  1  0  0  0  0
 14 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  2  0  0  0  0
 25 31  1  0  0  0  0
 14 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 32 38  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
   -4.1288    1.9787    1.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2330    1.3824    1.0739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321    0.6220    1.4755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718    0.4905    2.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435    0.0365    0.4636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8760    1.0785   -0.5778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    2.0921   -1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    2.9979   -2.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8968    3.9886   -2.5678 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2428    2.8548   -2.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.8591   -1.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    1.8292   -2.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530    0.9680   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9767   -0.2204   -0.2111 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4360   -0.2401   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0838   -0.5539   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4480   -0.6374   -1.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2467   -0.4152   -0.3791 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6217   -0.5012   -0.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523   -0.1083    0.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2531   -0.0245    0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5859   -1.5238   -0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065   -2.3140   -1.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158   -1.9061   -0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2219   -3.0289   -1.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352   -3.4198   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505   -4.5579   -2.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4447   -2.6655   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373   -1.5265   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426   -0.8540    0.3761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283   -1.1371   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1870   -0.1538    1.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755   -1.3774    1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407   -1.3711    3.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679   -0.1287    3.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.0930    5.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6824    1.1005    3.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    1.0723    1.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1864    1.3705    2.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161    3.0382    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1543    1.9006    1.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6692    2.1885   -0.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    4.6415   -3.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6710    3.5764   -3.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6948    2.5059   -2.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -0.7456   -2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -0.8814   -2.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0646   -0.7240   -1.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2651    0.0738    1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8166    0.2070    1.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -3.6204   -2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315   -4.5157   -3.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984   -2.9503   -0.9867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0101   -1.1155    0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1180   -2.3287    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6065   -2.2865    3.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477    2.0359    3.6588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0372    1.3276 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
  5  3  1  1
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  1
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 14 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 14 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 31  5  1  0
 38 32  1  0
 32  5  1  0
 13  6  1  0
 21 15  1  0
 31 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  7 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 16 46  1  0
 17 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 25 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 33 55  1  0
 34 56  1  0
 37 57  1  0
 38 58  1  0
M  END


  Mrv1533004201506032D          

 38 43  0  0  0  0            999 V2000
    1.9950    1.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174    0.7809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931   -0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9470   -0.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5565   -0.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438    0.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -2.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.6456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571   -1.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0913   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4434   -3.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3972   -1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0064   -1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7928   -1.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0428   -0.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656    0.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -0.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025   -2.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -3.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9980   -4.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749   -4.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8110   -5.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155   -3.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0794   -3.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543   -1.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883   -1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855   -1.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6486   -0.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -0.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173   -0.5093    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
  5 24  1  0  0  0  0
 17 24  1  0  0  0  0
 14 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  2  0  0  0  0
 25 31  1  0  0  0  0
 14 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 32 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12C3=CC(O)=CC(O)=C3C(C3=CC=C(O)C=C3)(C(=O)C3=CC(O)=CC(O)=C13)C21C=CC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H20O9/c1-38-26(37)29-20-11-18(33)13-22(35)24(20)28(14-2-4-15(30)5-3-14,27(29)8-6-16(31)7-9-27)25(36)19-10-17(32)12-21(34)23(19)29/h2-13,30,32-35H,1H3

> <INCHI_KEY>
PBGSPYHKIMHMQD-UHFFFAOYSA-N

> <FORMULA>
C29H20O9

> <MOLECULAR_WEIGHT>
512.47

> <EXACT_MASS>
512.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
49.748046891471375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.4885931763333344

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.878041034926346

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.2421466152954

> <JCHEM_PKA_STRONGEST_BASIC>
-5.677387259009909

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
136.6552

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       3.724   3.019   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.712   1.479   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.039   0.698   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.379   1.458   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.027  -0.842   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.634  -1.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.926  -0.302   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.039  -0.885   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.082   0.172   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.684  -2.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.945  -3.852   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.450  -4.938   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.280  -2.998   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.231  -4.209   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.770  -4.221   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.428  -5.614   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.740  -3.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.208  -3.490   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.345  -2.452   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.813  -2.918   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.014  -0.948   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.547  -0.482   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.216   1.022   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.409  -1.521   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.551  -5.591   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.409  -6.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.730  -8.253   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.193  -8.356   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.514  -9.738   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.336  -7.076   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.015  -5.694   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.208  -2.426   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.152  -3.546   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.653  -3.192   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.211  -1.717   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.288  -1.362   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.267  -0.596   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.766  -0.951   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24   32                                             
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   25   32                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   17                                                  
CONECT   25   14   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   14    5   33   38                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   32                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0,.0,]hexadecan]-2,2'(7'),3',5,5',10'(15'),11',13'-octaene-1'-carboxylic acid	Generator
Methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2'(7'),3',5,5',10'(15'),11',13'-octaene-1'-carboxylic acid	Generator

Chemical Formula

C₂₉H₂₀O₉

Average Mass

512.4700 Da

Monoisotopic Mass

512.11073 Da

IUPAC Name

methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate

Traditional Name

methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12C3=CC(O)=CC(O)=C3C(C3=CC=C(O)C=C3)(C(=O)C3=CC(O)=CC(O)=C13)C21C=CC(=O)C=C1

InChI Identifier

InChI=1S/C29H20O9/c1-38-26(37)29-20-11-18(33)13-22(35)24(20)28(14-2-4-15(30)5-3-14,27(29)8-6-16(31)7-9-27)25(36)19-10-17(32)12-21(34)23(19)29/h2-13,30,32-35H,1H3

InChI Key

PBGSPYHKIMHMQD-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
Hopea reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryltetralin lignans. These are lignans with a structure based on the 1-phenyltetralin skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Aryltetralin lignans

Sub Class

Not Available

Direct Parent

Aryltetralin lignans

Alternative Parents

Substituents

1-aryltetralin lignan
Phenylnaphthalene
Dibenzocycloheptene
1-naphthalenecarboxylic acid or derivatives
Tetralin
Indane
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Methyl ester
Cyclic ketone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.53	ALOGPS
logP	3.49	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.24	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.66 m³·mol⁻¹	ChemAxon
Polarizability	49.75 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

73227503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate (NP0154074)

MOL for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

3D MOL for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

3D SDF for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

3D-SDF for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

PDB for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

3D PDB for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

SMILES for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

INCHI for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

Structure for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)

3D Structure for NP0154074 (methyl 3',5',11',13'-tetrahydroxy-9'-(4-hydroxyphenyl)-4,8'-dioxospiro[cyclohexane-1,16'-tetracyclo[7.6.1.0²,⁷.0¹⁰,¹⁵]hexadecan]-2,2',4',5,6',10',12',14'-octaene-1'-carboxylate)