NP-MRD: Showing NP-Card for (+)-Sphenadilactone C (NP0073745)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 18:58:13 UTC

Updated at

2022-04-28 18:58:13 UTC

NP-MRD ID

NP0073745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sphenadilactone C

Description

N-[(1S,3R,7R,10S,12S,15S,17S,18R,21R,22S,23R,25S,29S)-14,18,23-trihydroxy-9,9,18,23,25-pentamethyl-5,19,24-trioxo-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]Nonacos-13-en-12-yl]ethanimidic acid belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (+)-Sphenadilactone C is found in Schisandra sphenanthera . Based on a literature review very few articles have been published on N-[(1S,3R,7R,10S,12S,15S,17S,18R,21R,22S,23R,25S,29S)-14,18,23-trihydroxy-9,9,18,23,25-pentamethyl-5,19,24-trioxo-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1¹⁵,²².0¹,¹³.0³,⁷.0³,¹⁰.0¹⁷,²¹.0²⁵,²⁹]Nonacos-13-en-12-yl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220582D          

 44 51  0  0  1  0            999 V2000
    6.6467   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4929   -0.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943   -1.0931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0607   -1.9249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6133   -2.6505    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7493   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971   -2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2799   -1.1106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0061   -1.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083   -1.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171   -0.5389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9906    0.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4316    0.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088    0.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740   -0.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141   -0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -1.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -2.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5480   -1.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531    1.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715    0.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292    0.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0334    1.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8490    1.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604    2.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4532    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1869   -3.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0080   -4.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9548   -2.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8858   -2.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4664   -1.5197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2429   -0.7256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4387   -0.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9290   -0.2676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5767   -0.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3708   -0.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2908   -1.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5529    0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3623    0.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3587   -3.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7793   -2.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -3.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9543    0.3975    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  3  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  1  0  0  0
 13 20  1  0  0  0  0
 13 21  1  0  0  0  0
 12 22  1  6  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
  3 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 32 38  1  6  0  0  0
 35 39  1  6  0  0  0
 35 40  1  1  0  0  0
 30 41  1  1  0  0  0
 30 42  1  6  0  0  0
  5 43  1  6  0  0  0
  2 44  1  0  0  0  0
M  END

     RDKit          3D

 83 90  0  0  0  0  0  0  0  0999 V2000
    1.6487    4.7681    2.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    3.8900    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    4.3875    0.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7268    2.4948    1.4373 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070    1.6001    0.3089 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1076    0.6867    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    0.1727   -0.8549 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9184   -0.3031   -0.8041 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7176    0.3420    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583    0.1134   -2.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -1.6736   -0.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902   -2.0894   -0.4929 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3682   -3.3518   -1.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3185   -2.7723   -2.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742   -3.4391   -3.7010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -1.3901   -2.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.0892   -1.2618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3888   -1.1681   -1.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733   -0.6188   -0.3396 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2619   -1.6446    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -1.1671    1.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0227   -1.1793    1.6299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7306   -0.9946    2.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3798   -2.4897    1.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921   -3.5664    1.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043   -2.2775   -0.0508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5484   -3.1267    0.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358   -2.5910   -1.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6689   -0.7855    0.0059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5089   -0.1316    0.7029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5266    0.4111   -0.2718 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1876    1.3366   -1.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1888    0.8675   -1.8312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9402   -0.3085   -1.3587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3398    0.0051   -1.4473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4502    1.3786   -1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3837    2.0201   -0.6919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2568    1.9572   -1.9386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8544    3.1819   -1.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4840    2.3547   -3.2308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7973   -0.5023   -0.9647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4862    1.2275    0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    2.3118    1.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    0.7292    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038    5.7817    2.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876    4.3982    3.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5995    4.9702    3.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    2.1082    2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277    2.2224   -0.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8156   -0.1051    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.2902    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.0005   -1.5832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381    1.4237    0.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434    0.0214    1.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -0.0081    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5097    0.6524   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9015    0.7909   -2.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7228   -0.7773   -2.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4892   -2.1482    0.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2055   -4.0427   -1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -3.8002   -1.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -2.2576   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0729   -0.7269   -2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1668   -2.1210    1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369   -2.4719    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3966   -1.9486    2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1788   -0.2401    2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078   -1.9736    3.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0719   -0.4726    3.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6469   -0.3853    2.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455   -4.1727    0.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1558   -3.0081   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1798   -2.7757    0.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1066   -3.3574   -1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5432   -0.7247    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8953    0.7339    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001    0.7337   -2.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8033   -1.1337   -2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3637    4.0512   -1.5855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7513    3.2889   -1.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1674    3.0177   -0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0694    1.7126   -3.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5973    2.8774    1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 17 16  1  6
 17 18  1  0
 19 18  1  6
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 30  1  0
 30 29  1  0
 29 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 38 40  1  6
 38 33  1  0
 33 32  1  0
 31 32  1  6
 31 41  1  0
 31 42  1  0
 42 43  1  0
 42 44  2  0
 29 26  1  0
 26 27  1  0
 26 28  1  6
 26 24  1  0
 24 25  2  0
 44  5  1  0
 17  7  1  0
 41 19  1  0
 17 12  1  0
 44 19  1  0
 24 22  1  0
 31 30  1  0
 33 34  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  4 48  1  0
  5 49  1  6
  6 50  1  0
  6 51  1  0
  7 52  1  6
  9 53  1  0
  9 54  1  0
  9 55  1  0
 10 56  1  0
 10 57  1  0
 10 58  1  0
 12 59  1  1
 13 60  1  0
 13 61  1  0
 18 62  1  0
 18 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 23 68  1  0
 23 69  1  0
 23 70  1  0
 30 76  1  1
 29 75  1  1
 34 78  1  6
 39 79  1  0
 39 80  1  0
 39 81  1  0
 40 82  1  0
 33 77  1  6
 43 83  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
M  END


  Mrv1652304282220582D          

 44 51  0  0  1  0            999 V2000
    6.6467   -0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4929   -0.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943   -1.0931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0607   -1.9249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6133   -2.6505    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7493   -2.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1971   -2.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2799   -1.1106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0061   -1.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083   -1.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7171   -0.5389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9906    0.2832    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4316    0.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088    0.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740   -0.3215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141   -0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7497   -1.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -2.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5480   -1.4050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531    1.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444    1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6715    0.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4292    0.4730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0334    1.0347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8490    1.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0604    2.0813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4532    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1869   -3.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0080   -4.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9548   -2.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8858   -2.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4664   -1.5197    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2429   -0.7256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4387   -0.5310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9290   -0.2676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5767   -0.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3708   -0.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2908   -1.5525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5529    0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3623    0.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3587   -3.6801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7793   -2.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -3.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9543    0.3975    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  3  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  1  0  0  0
 13 20  1  0  0  0  0
 13 21  1  0  0  0  0
 12 22  1  6  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
  3 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 32 38  1  6  0  0  0
 35 39  1  6  0  0  0
 35 40  1  1  0  0  0
 30 41  1  1  0  0  0
 30 42  1  6  0  0  0
  5 43  1  6  0  0  0
  2 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@H]1C[C@H]2C(C)(C)O[C@@H]3CC(=O)O[C@]23C[C@]23CC[C@@]4(C)[C@@H]5[C@@H]([C@H]6OC(=O)[C@](C)(O)[C@H]6O[C@@]5(O2)C(O)=C13)[C@@](C)(O)C4=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H39NO12/c1-12(33)32-13-9-14-25(2,3)41-15-10-16(34)42-30(14,15)11-29-8-7-26(4)20-18(27(5,38)23(26)36)19-22(28(6,39)24(37)40-19)43-31(20,44-29)21(35)17(13)29/h13-15,18-20,22,35,38-39H,7-11H2,1-6H3,(H,32,33)/t13-,14-,15+,18+,19+,20-,22-,26-,27+,28+,29-,30+,31-/m0/s1

> <INCHI_KEY>
PYUNFEXAYKBOOH-TXFVPDFUSA-N

> <FORMULA>
C31H39NO12

> <MOLECULAR_WEIGHT>
617.648

> <EXACT_MASS>
617.2472257

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.965233299555656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1S,3R,7R,10S,12S,15S,17S,18R,21R,22S,23R,25S,29S)-14,18,23-trihydroxy-9,9,18,23,25-pentamethyl-5,19,24-trioxo-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacos-13-en-12-yl]acetamide

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
-0.5996928196666674

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.546031849432923

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.343272539643125

> <JCHEM_PKA_STRONGEST_BASIC>
-1.153963029456683

> <JCHEM_POLAR_SURFACE_AREA>
187.15

> <JCHEM_REFRACTIVITY>
145.89950000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S,3R,7R,10S,12S,15S,17S,18R,21R,22S,23R,25S,29S)-14,18,23-trihydroxy-9,9,18,23,25-pentamethyl-5,19,24-trioxo-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1^{15,22}.0^{1,13}.0^{3,7}.0^{3,10}.0^{17,21}.0^{25,29}]nonacos-13-en-12-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      12.407  -0.576   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.987  -0.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.549  -2.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.047  -3.593   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.212  -4.948   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.599  -5.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.568  -3.756   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.723  -2.073   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.078  -2.248   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.095  -2.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.805  -1.006   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.316   0.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.272   1.651   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.923   0.926   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.232  -0.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.186  -1.754   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.000  -3.060   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.451  -4.499   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.490  -2.623   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.246   2.844   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.736   3.095   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.587   1.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.001   0.883   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      13.129   1.932   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      12.785   3.433   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.313   3.885   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.913   4.481   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.282  -6.127   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.948  -7.630   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      16.716  -5.527   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.587  -3.966   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.671  -2.837   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.253  -1.354   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.752  -0.991   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.534  -0.499   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.743  -1.453   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      21.226  -1.036   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      19.209  -2.898   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      17.832   0.871   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      19.343   0.811   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      17.470  -6.869   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      18.255  -5.577   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      13.617  -6.368   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      14.848   0.742   0.000  0.00  0.00           O+0
CONECT    1    2    8   23                                                  
CONECT    2    1    3   44                                                  
CONECT    3    2    4    9   34                                             
CONECT    4    3    5   31                                                  
CONECT    5    4    6   28   43                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    1    9   10                                             
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   15   19                                             
CONECT   12   11   13   22                                                  
CONECT   13   12   14   20   21                                             
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   12   23                                                       
CONECT   23   22    1   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   41   42                                             
CONECT   31   30    4   32                                                  
CONECT   32   31   33   38                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33    3                                                       
CONECT   35   33   36   39   40                                             
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   32                                                       
CONECT   39   35                                                            
CONECT   40   35                                                            
CONECT   41   30                                                            
CONECT   42   30                                                            
CONECT   43    5                                                            
CONECT   44    2                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Value	Source
N-[(1S,3R,7R,10S,12S,15S,17S,18R,21R,22S,23R,25S,29S)-14,18,23-Trihydroxy-9,9,18,23,25-pentamethyl-5,19,24-trioxo-4,8,16,20,28-pentaoxaoctacyclo[13.12.1.1,.0,.0,.0,.0,.0,]nonacos-13-en-12-yl]ethanimidate	Generator

Chemical Formula

C₃₁H₃₉NO₁₂

Average Mass

617.6480 Da

Monoisotopic Mass

617.24723 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H]1C[C@H]2C(C)(C)O[C@@H]3CC(=O)O[C@]23C[C@]23CC[C@@]4(C)[C@@H]5[C@@H]([C@H]6OC(=O)[C@](C)(O)[C@H]6O[C@@]5(O2)C(O)=C13)[C@@](C)(O)C4=O

InChI Identifier

InChI=1S/C31H39NO12/c1-12(33)32-13-9-14-25(2,3)41-15-10-16(34)42-30(14,15)11-29-8-7-26(4)20-18(27(5,38)23(26)36)19-22(28(6,39)24(37)40-19)43-31(20,44-29)21(35)17(13)29/h13-15,18-20,22,35,38-39H,7-11H2,1-6H3,(H,32,33)/t13-,14-,15+,18+,19+,20-,22-,26-,27+,28+,29-,30+,31-/m0/s1

InChI Key

PYUNFEXAYKBOOH-TXFVPDFUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Schisandra sphenanthera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Furopyran
Furofuran
Ketal
Oxepane
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Acyloin
Acetamide
Tetrahydrofuran
Tertiary alcohol
Furan
Dihydrofuran
Cyclic alcohol
Secondary carboxylic acid amide
Lactone
Ketone
Carboxylic acid ester
Carboxamide group
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Enol
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.79	ALOGPS
logP	-0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	145.9 m³·mol⁻¹	ChemAxon
Polarizability	61.97 Å³	ChemAxon
Number of Rings	8	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

25141318

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sphenadilactone C (NP0073745)

MOL for NP0073745 ((+)-Sphenadilactone C)

3D MOL for NP0073745 ((+)-Sphenadilactone C)

3D SDF for NP0073745 ((+)-Sphenadilactone C)

3D-SDF for NP0073745 ((+)-Sphenadilactone C)

PDB for NP0073745 ((+)-Sphenadilactone C)

3D PDB for NP0073745 ((+)-Sphenadilactone C)

SMILES for NP0073745 ((+)-Sphenadilactone C)

INCHI for NP0073745 ((+)-Sphenadilactone C)

Structure for NP0073745 ((+)-Sphenadilactone C)

3D Structure for NP0073745 ((+)-Sphenadilactone C)