NP-MRD: Showing NP-Card for turrapubin D (NP0043472)

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Record Information

Version

1.0

Created at

2021-06-21 00:52:28 UTC

Updated at

2021-06-30 00:19:10 UTC

NP-MRD ID

NP0043472

Secondary Accession Numbers

None

Natural Product Identification

Common Name

turrapubin D

Provided By

JEOL Database JEOL Logo

Description

TURRAPUBIN D belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. turrapubin D is found in Turraea pubescens. It was first documented in 2021 (PMID: 34610616). Based on a literature review a significant number of articles have been published on TURRAPUBIN D (PMID: 34610566) (PMID: 34610527) (PMID: 34610525) (PMID: 34610470) (PMID: 34610433) (PMID: 34610423).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102523D          

 73 78  0  0  0  0            999 V2000
    3.0767    2.1937    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.0045    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0296    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137   -1.4996    0.5430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4427   -2.3227    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5004   -0.3410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7274   -1.5579    0.7467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9391   -0.7775    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -1.1769    0.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.5188   -0.4989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7304    1.5580    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    0.2082   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0689    2.3926   -0.9501 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6132   -1.9677   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9370   -5.6757    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7486   -1.6685    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862   -0.4826    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -1.2958   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  2  1  0  0  0  0
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 24 61  1  0  0  0  0
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 24 63  1  0  0  0  0
M  END

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
    3.0767    2.1937    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.0045    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0296    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137   -1.4996    0.5430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4427   -2.3227    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8294   -1.8802   -0.1908 C   0  0  2  0  0  0  0  0  0  0  0  0
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 34 28  1  0
 33 32  1  0
 32 31  1  0
 31 30  2  0
 30 29  1  0
 28 26  1  0
 22 23  1  0
  1  2  2  3
 23 24  1  0
  8  9  2  0
 23 25  2  0
  7 43  1  0
  7 44  1  0
  6 42  1  6
 14 52  1  0
 14 53  1  0
  1 38  1  0
  1 39  1  0
 21 60  1  6
  4 41  1  1
 35 73  1  1
 34 71  1  0
 34 72  1  0
 28 67  1  6
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 20 57  1  0
 20 58  1  0
 20 59  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 18 54  1  0
 18 55  1  0
 18 56  1  0
 33 70  1  0
 31 69  1  0
 30 68  1  0
 24 61  1  0
 24 62  1  0
 24 63  1  0
M  END


  Mrv1652306212102523D          

 73 78  0  0  0  0            999 V2000
    3.0767    2.1937    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.0045    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0296    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137   -1.4996    0.5430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4427   -2.3227    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5004   -0.3410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7274   -1.5579    0.7467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9391   -0.7775    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -1.1769    0.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.5188   -0.4989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7304    1.5580    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    0.2082   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    1.0238   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0689    2.3926   -0.9501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3375    3.5829   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.6267    1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574    4.6008   -0.9055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    5.7739   -0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -0.0727   -0.5959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3656   -0.0082   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294   -1.8802   -0.1908 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2580   -3.1544    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -4.1882   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235   -5.4422    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -4.1200   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9253   -0.8173    0.0337 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3335   -0.7244    1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1858   -0.9689   -0.8976 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2606   -1.9292   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2434   -1.8055    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0040   -2.9499    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5744   -3.7682   -0.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5345   -3.1420   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6867    0.4956   -1.0719 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4243    1.3118   -1.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3932    0.7598   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3286    0.5179   -0.4322 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8871    2.9141    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4841    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.1654    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -1.7693    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824   -1.9420   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -1.1620    1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -2.6001    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568    1.1727    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    1.8232    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272    2.4710   -0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -0.6455   -2.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -0.0598   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9181    1.0645   -2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    1.1909    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119    2.4588   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403    2.5337   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927    5.5514    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    6.1865    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831    6.5183   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.0668   -2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012    0.9169   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0356   -0.8379   -2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.9677   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8027   -6.2721   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -5.6757    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853   -5.3203    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    0.0641    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486   -1.6685    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862   -0.4826    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -1.2958   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828   -0.9857    1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8461   -3.3112    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0929   -3.6735   -1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423    0.8115   -0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2298    0.6190   -2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5209    2.3780   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
 10 11  1  1  0  0  0
 10 13  1  0  0  0  0
 10 12  1  0  0  0  0
 19  6  1  0  0  0  0
  6  5  1  0  0  0  0
 19 13  1  0  0  0  0
 19 20  1  6  0  0  0
  4  5  1  0  0  0  0
 37 36  1  6  0  0  0
 35 36  1  0  0  0  0
  3  4  1  0  0  0  0
 21 22  1  0  0  0  0
  2 37  1  0  0  0  0
 26 27  1  1  0  0  0
 26 21  1  0  0  0  0
 28 29  1  0  0  0  0
 21  4  1  0  0  0  0
  3 40  1  1  0  0  0
 26 37  1  0  0  0  0
 13 51  1  1  0  0  0
  7  8  1  0  0  0  0
 14 15  1  0  0  0  0
  7  6  1  0  0  0  0
 15 16  2  0  0  0  0
  8 10  1  0  0  0  0
 15 17  1  0  0  0  0
 19  3  1  0  0  0  0
 17 18  1  0  0  0  0
 29 33  2  0  0  0  0
 13 14  1  0  0  0  0
 37 35  1  0  0  0  0
 35 34  1  0  0  0  0
 34 28  1  0  0  0  0
 33 32  1  0  0  0  0
 32 31  1  0  0  0  0
 31 30  2  0  0  0  0
 30 29  1  0  0  0  0
 28 26  1  0  0  0  0
 22 23  1  0  0  0  0
  1  2  2  3  0  0  0
 23 24  1  0  0  0  0
  8  9  2  0  0  0  0
 23 25  2  0  0  0  0
  7 43  1  0  0  0  0
  7 44  1  0  0  0  0
  6 42  1  6  0  0  0
 14 52  1  0  0  0  0
 14 53  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
 21 60  1  6  0  0  0
  4 41  1  1  0  0  0
 35 73  1  1  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
 28 67  1  6  0  0  0
 11 45  1  0  0  0  0
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 11 47  1  0  0  0  0
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 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 20 57  1  0  0  0  0
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 20 59  1  0  0  0  0
 27 64  1  0  0  0  0
 27 65  1  0  0  0  0
 27 66  1  0  0  0  0
 18 54  1  0  0  0  0
 18 55  1  0  0  0  0
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 33 70  1  0  0  0  0
 31 69  1  0  0  0  0
 30 68  1  0  0  0  0
 24 61  1  0  0  0  0
 24 62  1  0  0  0  0
 24 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1[C@]2([H])[C@@]([H])(O[C@@]3([H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)OC([H])([H])[H])[C@@]23C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O8/c1-14-23-24(36-20-12-19(31)26(3,4)18(27(20,23)5)11-22(32)33-7)25(35-15(2)30)28(6)17(16-8-9-34-13-16)10-21-29(14,28)37-21/h8-9,13,17-18,20-21,23-25H,1,10-12H2,2-7H3/t17-,18-,20-,21+,23+,24+,25-,27+,28+,29+/m0/s1

> <INCHI_KEY>
RVOBFAWYZMLHLH-FIOAHQOWSA-N

> <FORMULA>
C29H36O8

> <MOLECULAR_WEIGHT>
512.599

> <EXACT_MASS>
512.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.123526024337224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,3S,5R,7R,8R,9R,10R,12S,16R,17S)-9-(acetyloxy)-7-(furan-3-yl)-8,15,15,17-tetramethyl-2-methylidene-14-oxo-4,11-dioxapentacyclo[8.7.0.0^{3,5}.0^{3,8}.0^{12,17}]heptadecan-16-yl]acetate

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.0720110089999992

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.049008479679333

> <JCHEM_PKA_STRONGEST_BASIC>
-2.840358495215596

> <JCHEM_POLAR_SURFACE_AREA>
104.57000000000001

> <JCHEM_REFRACTIVITY>
129.9637

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,3S,5R,7R,8R,9R,10R,12S,16R,17S)-9-(acetyloxy)-7-(furan-3-yl)-8,15,15,17-tetramethyl-2-methylidene-14-oxo-4,11-dioxapentacyclo[8.7.0.0^{3,5}.0^{3,8}.0^{12,17}]heptadecan-16-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 73 78  0  0  0  0  0  0  0  0999 V2000
    3.0767    2.1937    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.0045    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0296    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137   -1.4996    0.5430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4427   -2.3227    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5004   -0.3410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7274   -1.5579    0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -0.7775    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -1.1769    0.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.5188   -0.4989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7304    1.5580    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    0.2082   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    1.0238   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0689    2.3926   -0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    3.5829   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.6267    1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7574    4.6008   -0.9055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    5.7739   -0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -0.0727   -0.5959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3656   -0.0082   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294   -1.8802   -0.1908 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2580   -3.1544    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -4.1882   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235   -5.4422    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -4.1200   -1.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9253   -0.8173    0.0337 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3335   -0.7244    1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1858   -0.9689   -0.8976 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2606   -1.9292   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2434   -1.8055    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0040   -2.9499    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5744   -3.7682   -0.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5345   -3.1420   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6867    0.4956   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243    1.3118   -1.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3932    0.7598   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3286    0.5179   -0.4322 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8871    2.9141    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4841    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.1654    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -1.7693    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824   -1.9420   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -1.1620    1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -2.6001    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568    1.1727    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    1.8232    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272    2.4710   -0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -0.6455   -2.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -0.0598   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9181    1.0645   -2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1726    1.1909    0.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119    2.4588   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403    2.5337   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9927    5.5514    0.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    6.1865    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831    6.5183   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.0668   -2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012    0.9169   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0356   -0.8379   -2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.9677   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8027   -6.2721   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -5.6757    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853   -5.3203    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    0.0641    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486   -1.6685    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862   -0.4826    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -1.2958   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828   -0.9857    1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8461   -3.3112    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0929   -3.6735   -1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423    0.8115   -0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2298    0.6190   -2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5209    2.3780   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
 10 11  1  1
 10 13  1  0
 10 12  1  0
 19  6  1  0
  6  5  1  0
 19 13  1  0
 19 20  1  6
  4  5  1  0
 37 36  1  6
 35 36  1  0
  3  4  1  0
 21 22  1  0
  2 37  1  0
 26 27  1  1
 26 21  1  0
 28 29  1  0
 21  4  1  0
  3 40  1  1
 26 37  1  0
 13 51  1  1
  7  8  1  0
 14 15  1  0
  7  6  1  0
 15 16  2  0
  8 10  1  0
 15 17  1  0
 19  3  1  0
 17 18  1  0
 29 33  2  0
 13 14  1  0
 37 35  1  0
 35 34  1  0
 34 28  1  0
 33 32  1  0
 32 31  1  0
 31 30  2  0
 30 29  1  0
 28 26  1  0
 22 23  1  0
  1  2  2  3
 23 24  1  0
  8  9  2  0
 23 25  2  0
  7 43  1  0
  7 44  1  0
  6 42  1  6
 14 52  1  0
 14 53  1  0
  1 38  1  0
  1 39  1  0
 21 60  1  6
  4 41  1  1
 35 73  1  1
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 33 70  1  0
 31 69  1  0
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 24 61  1  0
 24 62  1  0
 24 63  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.077   2.194   0.920  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.151   1.004   0.297  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.037  -0.030   0.441  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.514  -1.500   0.543  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.443  -2.323   0.040  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.331  -1.500  -0.341  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.727  -1.558   0.747  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.939  -0.778   0.307  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.068  -1.177   0.598  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.716   0.519  -0.499  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.730   1.558   0.028  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.083   0.208  -1.960  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.235   1.024  -0.281  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.069   2.393  -0.950  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.338   3.583  -0.106  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.266   3.627   1.115  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.757   4.601  -0.906  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.155   5.774  -0.194  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.866  -0.073  -0.596  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.366  -0.008  -2.056  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.829  -1.880  -0.191  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.258  -3.154   0.345  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.375  -4.188  -0.530  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.723  -5.442   0.212  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.246  -4.120  -1.744  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.925  -0.817   0.034  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.333  -0.724   1.527  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.186  -0.969  -0.898  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.261  -1.929  -0.490  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.243  -1.806   0.536  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.004  -2.950   0.498  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.574  -3.768  -0.493  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.535  -3.142  -1.095  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.687   0.496  -1.072  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.424   1.312  -1.050  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.393   0.760  -1.860  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.329   0.518  -0.432  0.00  0.00           C+0
HETATM   38  H   UNK     0       3.887   2.914   0.871  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.207   2.484   1.503  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.579   0.165   1.424  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.616  -1.769   1.602  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.082  -1.942  -1.255  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.368  -1.162   1.702  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.017  -2.600   0.925  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.757   1.173   0.001  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.520   1.823   1.070  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.727   2.471  -0.575  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.532  -0.646  -2.359  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.144  -0.060  -2.044  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.918   1.065  -2.619  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.173   1.191   0.804  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.412   2.459  -1.930  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.140   2.534  -1.113  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.993   5.551   0.474  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.310   6.186   0.366  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.483   6.518  -0.925  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.538  -0.067  -2.768  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.901   0.917  -2.279  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.036  -0.838  -2.297  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.613  -1.968  -1.261  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.803  -6.272  -0.496  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.937  -5.676   0.934  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.685  -5.320   0.716  0.00  0.00           H+0
HETATM   64  H   UNK     0       6.076   0.064   1.692  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.749  -1.669   1.893  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.486  -0.483   2.176  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.828  -1.296  -1.887  0.00  0.00           H+0
HETATM   68  H   UNK     0       8.383  -0.986   1.227  0.00  0.00           H+0
HETATM   69  H   UNK     0       9.846  -3.311   1.072  0.00  0.00           H+0
HETATM   70  H   UNK     0       7.093  -3.674  -1.929  0.00  0.00           H+0
HETATM   71  H   UNK     0       7.342   0.812  -0.254  0.00  0.00           H+0
HETATM   72  H   UNK     0       7.230   0.619  -2.015  0.00  0.00           H+0
HETATM   73  H   UNK     0       5.521   2.378  -0.948  0.00  0.00           H+0
CONECT    1    2   38   39                                                  
CONECT    2    3   37    1                                                  
CONECT    3    2    4   40   19                                             
CONECT    4    5    3   21   41                                             
CONECT    5    6    4                                                       
CONECT    6   19    5    7   42                                             
CONECT    7    8    6   43   44                                             
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10   11   13   12    8                                             
CONECT   11   10   45   46   47                                             
CONECT   12   10   48   49   50                                             
CONECT   13   10   19   51   14                                             
CONECT   14   15   13   52   53                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   54   55   56                                             
CONECT   19    6   13   20    3                                             
CONECT   20   19   57   58   59                                             
CONECT   21   22   26    4   60                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   61   62   63                                             
CONECT   25   23                                                            
CONECT   26   27   21   37   28                                             
CONECT   27   26   64   65   66                                             
CONECT   28   29   34   26   67                                             
CONECT   29   28   33   30                                                  
CONECT   30   31   29   68                                                  
CONECT   31   32   30   69                                                  
CONECT   32   33   31                                                       
CONECT   33   29   32   70                                                  
CONECT   34   35   28   71   72                                             
CONECT   35   36   37   34   73                                             
CONECT   36   37   35                                                       
CONECT   37   36    2   26   35                                             
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   14                                                            
CONECT   54   18                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   24                                                            
CONECT   64   27                                                            
CONECT   65   27                                                            
CONECT   66   27                                                            
CONECT   67   28                                                            
CONECT   68   30                                                            
CONECT   69   31                                                            
CONECT   70   33                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
CONECT   73   35                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  156    0
END

RDKit          3D

73 78  0  0  0  0  0  0  0  0999 V2000
    3.0767    2.1937    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1511    1.0045    0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.0296    0.4408 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5137   -1.4996    0.5430 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4427   -2.3227    0.0397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5004   -0.3410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7274   -1.5579    0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391   -0.7775    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682   -1.1769    0.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    0.5188   -0.4989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7304    1.5580    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0834    0.2082   -1.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346    1.0238   -0.2811 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0689    2.3926   -0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    3.5829   -0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2661    3.6267    1.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1549    5.7739   -0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8658   -0.0727   -0.5959 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3656   -0.0082   -2.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294   -1.8802   -0.1908 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2580   -3.1544    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755   -4.1882   -0.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7235   -5.4422    0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9253   -0.8173    0.0337 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3335   -0.7244    1.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1858   -0.9689   -0.8976 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2606   -1.9292   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2434   -1.8055    0.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0040   -2.9499    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5744   -3.7682   -0.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5345   -3.1420   -1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6867    0.4956   -1.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243    1.3118   -1.0504 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3932    0.7598   -1.8601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3286    0.5179   -0.4322 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8871    2.9141    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4841    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    0.1654    1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -1.7693    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824   -1.9420   -1.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3681   -1.1620    1.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169   -2.6001    0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7568    1.1727    0.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    1.8232    1.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272    2.4710   -0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -0.6455   -2.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442   -0.0598   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9181    1.0645   -2.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4119    2.4588   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403    2.5337   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3099    6.1865    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831    6.5183   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.0668   -2.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012    0.9169   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0356   -0.8379   -2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -1.9677   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8027   -6.2721   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -5.6757    0.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853   -5.3203    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    0.0641    1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486   -1.6685    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862   -0.4826    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8281   -1.2958   -1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3828   -0.9857    1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8461   -3.3112    1.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0929   -3.6735   -1.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3423    0.8115   -0.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2298    0.6190   -2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5209    2.3780   -0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
 10 11  1  1
 10 13  1  0
 10 12  1  0
 19  6  1  0
  6  5  1  0
 19 13  1  0
 19 20  1  6
  4  5  1  0
 37 36  1  6
 35 36  1  0
  3  4  1  0
 21 22  1  0
  2 37  1  0
 26 27  1  1
 26 21  1  0
 28 29  1  0
 21  4  1  0
  3 40  1  1
 26 37  1  0
 13 51  1  1
  7  8  1  0
 14 15  1  0
  7  6  1  0
 15 16  2  0
  8 10  1  0
 15 17  1  0
 19  3  1  0
 17 18  1  0
 29 33  2  0
 13 14  1  0
 37 35  1  0
 35 34  1  0
 34 28  1  0
 33 32  1  0
 32 31  1  0
 31 30  2  0
 30 29  1  0
 28 26  1  0
 22 23  1  0
  1  2  2  3
 23 24  1  0
  8  9  2  0
 23 25  2  0
  7 43  1  0
  7 44  1  0
  6 42  1  6
 14 52  1  0
 14 53  1  0
  1 38  1  0
  1 39  1  0
 21 60  1  6
  4 41  1  1
 35 73  1  1
 34 71  1  0
 34 72  1  0
 28 67  1  6
 11 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 20 57  1  0
 20 58  1  0
 20 59  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 18 54  1  0
 18 55  1  0
 18 56  1  0
 33 70  1  0
 31 69  1  0
 30 68  1  0
 24 61  1  0
 24 62  1  0
 24 63  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₈

Average Mass

512.5990 Da

Monoisotopic Mass

512.24102 Da

IUPAC Name

methyl 2-[(1R,3S,5R,7R,8R,9R,10R,12S,16R,17S)-9-(acetyloxy)-7-(furan-3-yl)-8,15,15,17-tetramethyl-2-methylidene-14-oxo-4,11-dioxapentacyclo[8.7.0.0^{3,5}.0^{3,8}.0^{12,17}]heptadecan-16-yl]acetate

Traditional Name

methyl [(1R,3S,5R,7R,8R,9R,10R,12S,16R,17S)-9-(acetyloxy)-7-(furan-3-yl)-8,15,15,17-tetramethyl-2-methylidene-14-oxo-4,11-dioxapentacyclo[8.7.0.0^{3,5}.0^{3,8}.0^{12,17}]heptadecan-16-yl]acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1[C@]2([H])[C@@]([H])(O[C@@]3([H])C([H])([H])C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(C([H])([H])C(=O)OC([H])([H])[H])[C@@]23C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2(C([H])([H])[H])[C@]([H])(C3=C([H])OC([H])=C3[H])C([H])([H])[C@@]3([H])O[C@@]123

InChI Identifier

InChI=1S/C29H36O8/c1-14-23-24(36-20-12-19(31)26(3,4)18(27(20,23)5)11-22(32)33-7)25(35-15(2)30)28(6)17(16-8-9-34-13-16)10-21-29(14,28)37-21/h8-9,13,17-18,20-21,23-25H,1,10-12H2,2-7H3/t17-,18-,20-,21+,23+,24+,25-,27+,28+,29+/m0/s1

InChI Key

RVOBFAWYZMLHLH-FIOAHQOWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Turraea pubescens	JEOL database	Yuan, C. -M., et al, J. Nat. Prod. 76, 1166 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Dicarboxylic acid or derivatives
Oxane
Furan
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4	ALOGPS
logP	3.07	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	18.05	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.96 m³·mol⁻¹	ChemAxon
Polarizability	54.12 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	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

30825500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71725865

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tanaka T, Iwamoto K, Wada M, Yano E, Suzuki T, Kawaguchi N, Shirasaka N, Moriyama T, Homma Y: Dietary syringic acid reduces fat mass in an ovariectomy-induced mouse model of obesity. Menopause. 2021 Oct 4. pii: 00042192-900000000-96887. doi: 10.1097/GME.0000000000001853. [PubMed:34610616 ]
Venasse M, Gauthier A, Giroux I, Pilutti LA: Dietary intake and characteristics in persons with multiple sclerosis. Mult Scler Relat Disord. 2021 Sep 9;56:103237. doi: 10.1016/j.msard.2021.103237. [PubMed:34610566 ]
Zhang CL, Zhang JJ, Zhu QF, Guan HY, Yang YX, He X, Fu Y, Chen TX, Dong L, Yang XS, Tang KF, Xu GB, Liao SG: Antihyperuricemia and antigouty arthritis effects of Persicaria capitata herba in mice. Phytomedicine. 2021 Sep 23;93:153765. doi: 10.1016/j.phymed.2021.153765. [PubMed:34610527 ]
Koloski CW, Cassone BJ: Transcriptional profiling of Dermacentor variabilis (Acari: Ixodidae) provides insights into the role of the Haller's organ in spatial DEET recognition. Ticks Tick Borne Dis. 2021 Sep 24;13(1):101827. doi: 10.1016/j.ttbdis.2021.101827. [PubMed:34610525 ]
Cai M, Wang Z, Luu TTT, Zhang D, Finke B, He J, Tay LWR, Di Paolo G, Du G: PLD1 Promotes Reactive Oxygen Species Production in Vascular Smooth Muscle Cells and Injury-Induced Neointima Formation. Biochim Biophys Acta Mol Cell Biol Lipids. 2021 Oct 2:159062. doi: 10.1016/j.bbalip.2021.159062. [PubMed:34610470 ]
Abdollahzadeh R, Shushizadeh MH, Barazandehrokh M, Choopani S, Azarnezhad A, Paknahad S, Pirhoushiaran M, Makani SZ, Yeganeh RZ: Association of Vitamin D receptor gene polymorphisms and clinical/severe outcomes of COVID-19 patients. Infect Genet Evol. 2021 Oct 2:105098. doi: 10.1016/j.meegid.2021.105098. [PubMed:34610433 ]
Huang X, Chen H, Dai X, Xu M, Wang K, Feng Z: Design, synthesis, and structure-activity relationship of PD-1/PD-L1 inhibitors with a benzo[d]isoxazole scaffold. Bioorg Med Chem Lett. 2021 Oct 2;52:128403. doi: 10.1016/j.bmcl.2021.128403. [PubMed:34610423 ]
Zhang F, Zuo J, Jin W, Xu F, Jiang L, Xi D, Wen Y, Li J, Yu Z, Li Z, Xu R, Zhang G, Zhou C, Duan N: Size effect of gamma-MnO2 precoated anode on lead-containing pollutant reduction and its controllable fabrication in industrial-scale for zinc electrowinning. Chemosphere. 2021 Oct 2;287(Pt 4):132457. doi: 10.1016/j.chemosphere.2021.132457. [PubMed:34610373 ]
Taylor E, Heyland A: Evolution of non-genomic nuclear receptor function. Mol Cell Endocrinol. 2021 Oct 2:111468. doi: 10.1016/j.mce.2021.111468. [PubMed:34610359 ]
Lin Z, Luo P, Huang D, Wu Y, Li F, Liu H: Multi-omics based strategy for toxicity analysis of acrylamide in Saccharomyces cerevisiae model. Chem Biol Interact. 2021 Oct 2;349:109682. doi: 10.1016/j.cbi.2021.109682. [PubMed:34610338 ]
Yuan, C. -M., et al. (2013). Yuan, C. -M., et al, J. Nat. Prod. 76, 1166 (2013). J. Nat. Prod..

Showing NP-Card for turrapubin D (NP0043472)

MOL for NP0043472 (turrapubin D)

3D MOL for NP0043472 (turrapubin D)

3D SDF for NP0043472 (turrapubin D)

3D-SDF for NP0043472 (turrapubin D)

PDB for NP0043472 (turrapubin D)

3D PDB for NP0043472 (turrapubin D)

SMILES for NP0043472 (turrapubin D)

INCHI for NP0043472 (turrapubin D)

Structure for NP0043472 (turrapubin D)

3D Structure for NP0043472 (turrapubin D)