NP-MRD: Showing NP-Card for methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate (NP0232353)

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Record Information

Version

2.0

Created at

2022-09-06 13:34:06 UTC

Updated at

2022-09-06 13:34:07 UTC

NP-MRD ID

NP0232353

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate

Description

LLD-3 belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate is found in Lophanthera lactescens. methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate was first documented in 2009 (PMID: 19359020). Based on a literature review very few articles have been published on LLD-3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062215342D          

 56 61  0  0  1  0            999 V2000
   -0.7567    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0072    0.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6286    1.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8071    0.4294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6286    0.5056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1518    1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733    1.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2715    0.6581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9268   -0.0915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5821   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -0.7648    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0589   -1.5143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -2.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501   -1.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1909   -2.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2251   -0.6885    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7018   -1.3618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3571   -2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8339   -2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -2.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5698    0.0610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0465   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3912    0.1372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4675   -0.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2030   -1.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2170   -1.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8903   -0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2127    0.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360    0.8868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2592    1.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6039    2.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4377    1.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0930    0.7343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6163    1.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054   -0.1677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7606   -0.9172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2374   -1.5905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5997   -2.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3694   -3.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8798   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9392   -0.9935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5945   -1.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -2.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927   -2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -3.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624   -0.3202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1747   -1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612   -1.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0735   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5992   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400   -2.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615   -0.5180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0499   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0075   -0.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 31 30  1  1  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 10 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 11  1  1  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 43 48  1  0  0  0  0
  5 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
 48 54  1  0  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
  2 56  1  0  0  0  0
M  END

     RDKit          3D

110115  0  0  0  0  0  0  0  0999 V2000
   -4.3629   -5.0769    2.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -4.0318    2.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -4.3062    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7148   -3.4847    0.9504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352   -2.0497    0.7951 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0091   -1.5167   -0.4215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8060   -1.5608   -1.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1576   -2.4997   -0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0294   -1.8979   -1.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -0.5788   -1.3860 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4410    0.4340   -1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3131    0.8482   -2.3013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    1.6591   -0.6454 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9673    2.7552   -1.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    3.8795   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0639    5.0449   -2.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    4.0399    0.0215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6690    1.6342   -0.5586 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1612    2.9885   -0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    3.5303    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1598    4.9389    0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7688    2.8140    1.7129 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4099    0.9846   -1.6503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6174    1.9839   -2.8155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7824    0.5368   -1.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1123    0.3043    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -0.3403    0.9561 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    0.8301    0.7072 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6426    0.6244    2.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8756    1.2211   -1.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6468   -0.0806   -2.1868 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7859   -0.6904   -3.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821   -0.7372   -4.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -1.2777   -2.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -0.1252   -2.3091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0219    0.2881   -3.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3953   -0.2145   -0.0035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2350    0.5113    0.9002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8094    0.4641    2.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197    1.5070    3.0679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0715    1.3274    4.4628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6276    2.6549    2.6189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7098    0.1764    0.9599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3353    1.1051    1.7604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055    2.1357    1.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8226    3.0866    2.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4292    2.2077    0.0895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9986   -1.3066    1.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1678   -1.7154    0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5252   -3.0494    0.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5777   -3.5582   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8472   -5.0108   -0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2399   -2.7463   -1.1516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788   -1.4992    2.6026 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3886   -0.5159    3.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9245   -2.7648    2.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1372   -6.0579    2.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2170   -4.9143    3.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353   -5.3840    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9418   -4.0135    0.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348   -1.7230    1.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -2.4227   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -1.9287   -2.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625   -0.7292   -2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -3.3686   -1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951   -2.8076    0.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9419   -2.5990   -1.7802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7088   -1.9913   -2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0407   -0.7566   -0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    1.3445   -1.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2118    1.7097   -2.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4119    0.1151   -3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    1.9477    0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8829    5.5706   -1.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    5.8010   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1651    4.6580   -3.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8668    1.2010    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292    5.3908    1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3286    5.5255    0.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0596    5.1019    0.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284    2.8416   -2.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4737    1.5475   -3.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    2.4233   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1888    1.4582    2.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2067   -0.3396    2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7418    0.6326    2.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4247   -0.7963   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308   -1.1950   -5.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0078   -0.3059   -4.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216   -1.8655   -1.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0680   -1.9250   -3.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561   -0.4906   -4.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -0.6027    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2281    1.5895    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309062215342D          

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    3.3694   -3.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7400   -2.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
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 25 31  1  0  0  0  0
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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 10 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 11  1  1  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 38 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 43 48  1  0  0  0  0
  5 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  2  0  0  0  0
 48 54  1  0  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
  2 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232353

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12O[C@@H]1C(=C)C[C@@]1(O)[C@@H]3CC[C@@]4(C)[C@@H]5C=CC(=C)O[C@H](C)[C@@]5(COC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]4[C@@]3(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C41H54O15/c1-19-17-40(48)28-15-16-36(9)27-14-13-20(2)51-21(3)39(27,18-50-22(4)42)32(53-24(6)44)29(52-23(5)43)30(36)37(28,10)33(54-25(7)45)34(55-26(8)46)38(40,11)41(31(19)56-41)35(47)49-12/h13-14,21,27-34,48H,1-2,15-18H2,3-12H3/t21-,27+,28-,29+,30+,31-,32+,33-,34+,36+,37+,38-,39-,40-,41+/m1/s1

> <INCHI_KEY>
PGUFYOHQERCXID-BGKFFRIMSA-N

> <FORMULA>
C41H54O15

> <MOLECULAR_WEIGHT>
786.868

> <EXACT_MASS>
786.346271039

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
79.74895659173882

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,3S,4R,5R,6S,8R,11R,12R,15S,16S,21R,22R,23R,24S)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0^{2,12}.0^{5,11}.0^{6,8}.0^{16,22}]tetracos-17-ene-6-carboxylate

> <JCHEM_LOGP>
1.4733811606666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.885057016611075

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2864760609343167

> <JCHEM_POLAR_SURFACE_AREA>
199.78999999999996

> <JCHEM_REFRACTIVITY>
192.5728

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,3S,4R,5R,6S,8R,11R,12R,15S,16S,21R,22R,23R,24S)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0^{2,12}.0^{5,11}.0^{6,8}.0^{16,22}]tetracos-17-ene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.413   2.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.013   1.512   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.173   2.493   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.681   2.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.373   0.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.907   0.944   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.017   2.201   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.550   2.343   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.084   2.485   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.974   1.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.330  -0.171   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.687  -1.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.220  -1.428   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.577  -2.827   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.824  -4.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.547  -3.584   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.823  -5.483   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.753  -1.285   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.643  -2.542   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.000  -3.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.890  -5.198   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.467  -4.083   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.397   0.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.287  -1.143   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.930   0.256   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.073  -1.277   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.579  -2.736   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      13.472  -1.921   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.729  -1.031   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.464   0.398   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.574   1.655   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.684   2.912   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.327   4.311   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.150   2.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.507   1.371   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.617   2.628   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.797  -0.313   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.153  -1.712   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.043  -2.969   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.853  -4.725   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.290  -5.625   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.509  -3.963   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.620  -1.854   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.976  -3.254   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.866  -4.510   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.400  -4.368   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       3.223  -5.910   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       2.730  -0.598   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.193  -2.041   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       0.674  -2.297   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       0.137  -3.741   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       1.119  -4.928   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -1.381  -3.997   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.235  -0.967   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.093  -2.001   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       0.014  -0.028   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   56                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   48                                                  
CONECT    6    5    7    8   37                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12   13   37                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26   30   31                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   10   23   36                                             
CONECT   36   35                                                            
CONECT   37   11    6   38                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   38   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   43    5   49   54                                             
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   48   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    2                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₅₄O₁₅

Average Mass

786.8680 Da

Monoisotopic Mass

786.34627 Da

IUPAC Name

methyl (1S,2R,3S,4R,5R,6S,8R,11R,12R,15S,16S,21R,22R,23R,24S)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0^{2,12}.0^{5,11}.0^{6,8}.0^{16,22}]tetracos-17-ene-6-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12O[C@@H]1C(=C)C[C@@]1(O)[C@@H]3CC[C@@]4(C)[C@@H]5C=CC(=C)O[C@H](C)[C@@]5(COC(C)=O)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]4[C@@]3(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]21C

InChI Identifier

InChI=1S/C41H54O15/c1-19-17-40(48)28-15-16-36(9)27-14-13-20(2)51-21(3)39(27,18-50-22(4)42)32(53-24(6)44)29(52-23(5)43)30(36)37(28,10)33(54-25(7)45)34(55-26(8)46)38(40,11)41(31(19)56-41)35(47)49-12/h13-14,21,27-34,48H,1-2,15-18H2,3-12H3/t21-,27+,28-,29+,30+,31-,32+,33-,34+,36+,37+,38-,39-,40-,41+/m1/s1

InChI Key

PGUFYOHQERCXID-BGKFFRIMSA-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
Lophanthera lactescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
10-hydroxysteroid
Hydroxysteroid
Steroid
Oxepane
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Cyclic alcohol
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.47	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	199.79 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	192.57 m³·mol⁻¹	ChemAxon
Polarizability	79.75 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

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

101470671

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Danelli MG, Soares DC, Abreu HS, Pecanha LM, Saraiva EM: Leishmanicidal effect of LLD-3 (1), a nor-triterpene isolated from Lophanthera lactescens. Phytochemistry. 2009 Mar;70(5):608-14. doi: 10.1016/j.phytochem.2009.03.009. Epub 2009 Apr 7. [PubMed:19359020 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate (NP0232353)

MOL for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

3D MOL for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

3D SDF for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

3D-SDF for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

PDB for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

3D PDB for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

SMILES for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

INCHI for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

Structure for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)

3D Structure for NP0232353 (methyl (1s,2r,3s,4r,5r,6s,8r,11r,12r,15s,16s,21r,22r,23r,24s)-3,4,23,24-tetrakis(acetyloxy)-22-[(acetyloxy)methyl]-11-hydroxy-2,5,15,21-tetramethyl-9,19-dimethylidene-7,20-dioxahexacyclo[13.9.0.0²,¹².0⁵,¹¹.0⁶,⁸.0¹⁶,²²]tetracos-17-ene-6-carboxylate)