NP-MRD: Showing NP-Card for (9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate (NP0303758)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 18:23:00 UTC

Updated at

2022-09-10 18:23:01 UTC

NP-MRD ID

NP0303758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate

Description

(9R,13S,15R,16R,17R,18S)-18-(acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]Nonadeca-1(12),2,4,10-tetraen-15-yl acetate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate is found in Kadsura heteroclita. Based on a literature review very few articles have been published on (9R,13S,15R,16R,17R,18S)-18-(acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]Nonadeca-1(12),2,4,10-tetraen-15-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220232D          

 43 47  0  0  1  0            999 V2000
   -0.3842   -0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6656    0.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -0.8029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145   -1.4891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2913   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -2.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983   -2.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -3.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049   -3.2913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6129   -2.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0653   -2.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160   -2.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -2.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -3.6362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448   -3.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386   -4.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7100   -4.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216   -2.9150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6377   -3.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326   -3.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065   -3.2769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9926   -3.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -4.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1992   -4.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251   -5.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -2.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9215   -1.9415    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4105   -1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -1.4305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4505   -0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0982   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646   -0.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9833   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7497   -1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3356   -1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -2.2288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0070   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  6  0  0  0
 31 33  1  6  0  0  0
 34 31  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 34 41  1  0  0  0  0
 30 42  1  0  0  0  0
  5 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END

     RDKit          3D

 85 89  0  0  0  0  0  0  0  0999 V2000
    0.5427   -4.2853    2.9077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912   -3.8936    1.4790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -4.6997    0.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0863   -2.6431    1.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0230   -2.0951   -0.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5526   -2.1911   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -0.9237   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    0.1657    0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158    1.4030    0.7076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7220    1.5096    0.9370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8223    0.5187    0.8741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7284   -0.4223   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6321   -1.0257   -0.6875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7335   -0.9906   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8626   -0.3739   -1.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3658    0.9509   -1.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3631    1.4212   -1.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7801    1.6757   -0.0481 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1425    1.1626    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0393    0.1651    1.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9621    2.3205    2.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810    0.2617    0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0040    0.0166    1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.5477    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    1.1541   -0.6857 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5690    2.0728   -0.1732 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9438    3.1403   -0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9259    4.1727   -0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    3.2546   -2.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8243   -0.2762   -0.2295 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9331   -0.9999   -0.7990 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0385   -2.4126   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6776   -1.2905   -2.1689 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3209   -0.4811   -0.7728 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8627   -0.3396    0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2047    0.2930    0.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6910    1.0029   -0.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0404    1.5808   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.1789   -1.5253 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2734    1.8501   -2.5179 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6221    0.6142   -1.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262   -0.7385   -0.4008 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0729   -0.3173   -1.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151   -4.6910    3.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782   -5.0313    3.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -3.4442    3.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3679   -2.8120   -0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7748   -2.5921   -1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143   -2.9264    0.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8145    2.2977    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    2.5401    1.2218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6576   -0.1278    1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -1.7054   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340   -1.9519   -1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5237   -0.9076   -2.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736   -0.8716    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0750    0.2258    1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9859    0.2968    2.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8513    3.2916    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1846    2.1170    2.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9130    2.4332    2.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6928   -0.7604    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9601   -0.2052    2.5471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.9699    2.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5735    2.1296    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    2.1962   -0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3450    1.3246   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340    4.3050   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769    5.1518   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519    3.9217    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -0.1581    0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401   -2.7206   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -2.3624    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015   -3.1911   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -1.8519   -2.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9591   -1.3277   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1705    0.2262    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9927   -1.3384    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7981    0.1329    1.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4801    1.7311   -1.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0194    2.5213    0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6721    0.8564    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5632    0.6552   -1.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096   -0.3121   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8227   -1.0685   -2.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 29  2  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  1
 22  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 42  1  0
 42 43  1  6
 42 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  6
 31 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  0
 39 41  1  0
  7 13  1  0
 13 12  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 11  1  0
 11 10  1  0
 10  9  2  0
 30 25  1  0
 41 34  1  0
 11 12  1  0
 42 22  1  0
  9  8  1  0
 28 68  1  0
 28 69  1  0
 28 70  1  0
 25 67  1  6
 24 65  1  0
 24 66  1  0
 23 62  1  0
 23 63  1  0
 23 64  1  0
  6 48  1  0
  6 49  1  0
  5 47  1  6
  1 44  1  0
  1 45  1  0
  1 46  1  0
 43 83  1  0
 43 84  1  0
 43 85  1  0
 30 71  1  1
 32 72  1  0
 32 73  1  0
 32 74  1  0
 33 75  1  0
 34 76  1  6
 35 77  1  0
 35 78  1  0
 36 79  1  0
 38 80  1  0
 38 81  1  0
 38 82  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 21 61  1  0
 11 52  1  1
 10 51  1  0
  9 50  1  0
M  END


  Mrv1652309102220232D          

 43 47  0  0  1  0            999 V2000
   -0.3842   -0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -0.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6656    0.6230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726   -0.8029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1145   -1.4891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2913   -1.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668   -2.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1983   -2.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524   -3.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -3.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6049   -3.2913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6129   -2.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9729   -1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0653   -2.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4160   -2.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -2.9044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -3.6362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448   -3.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4386   -4.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7100   -4.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0216   -2.9150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6377   -3.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326   -3.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3065   -3.2769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9926   -3.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9389   -4.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1992   -4.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6251   -5.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -2.4525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9215   -1.9415    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4105   -1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325   -2.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692   -1.4305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4505   -0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0982   -0.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646   -0.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9833   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7497   -1.5304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3356   -1.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -2.2288    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0070   -1.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  6  0  0  0
 31 33  1  6  0  0  0
 34 31  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 34 41  1  0  0  0  0
 30 42  1  0  0  0  0
  5 42  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0303758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@]2(C)C3=C(C[C@H](OC(C)=O)[C@]2(C)[C@H]1[C@@](C)(O)[C@@H]1CC=C(C)C(=O)O1)C=C1C=CC(=O)OC(C)(C)[C@@H]1C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C34H42O9/c1-18-9-13-26(42-30(18)38)34(8,39)29-25(40-19(2)35)17-32(6)24-12-11-23-21(10-14-28(37)43-31(23,4)5)15-22(24)16-27(33(29,32)7)41-20(3)36/h9-12,14-15,23,25-27,29,39H,13,16-17H2,1-8H3/t23-,25-,26+,27+,29+,32+,33-,34+/m1/s1

> <INCHI_KEY>
OZGJHTKUIUKNKQ-MCFBLURZSA-N

> <FORMULA>
C34H42O9

> <MOLECULAR_WEIGHT>
594.701

> <EXACT_MASS>
594.282882932

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
64.53382346995514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,13S,15R,16R,17R,18S)-18-(acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0^{3,9}.0^{13,17}]nonadeca-1(12),2,4,10-tetraen-15-yl acetate

> <JCHEM_LOGP>
3.1106408489999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.69417461434795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.369968023684206

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000002

> <JCHEM_REFRACTIVITY>
160.73320000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9R,13S,15R,16R,17R,18S)-18-(acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0^{3,9}.0^{13,17}]nonadeca-1(12),2,4,10-tetraen-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.717  -0.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.254  -0.118   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.109   1.163   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.936  -1.499   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.080  -2.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.544  -2.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.311  -3.960   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.370  -5.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.284  -6.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.782  -7.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.996  -6.144   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.011  -4.604   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.816  -3.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.224  -3.655   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.722  -4.013   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.377  -5.407   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.917  -5.422   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.695  -6.788   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.190  -7.116   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.552  -8.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.192  -8.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.907  -5.441   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.190  -6.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.861  -6.650   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.305  -6.117   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.586  -6.972   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.486  -8.509   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.105  -9.190   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.767  -9.364   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.244  -4.578   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.453  -3.624   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.500  -2.415   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -6.407  -4.833   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -6.663  -2.670   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.441  -1.146   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.650  -0.193   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.081  -0.763   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -10.290   0.191   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.302  -2.287   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.733  -2.857   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -8.093  -3.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.762  -4.161   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.746  -2.976   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   42                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8   23   24   42                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   42                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   34                                                       
CONECT   42   30    5   22   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(9R,13S,15R,16R,17R,18S)-18-(Acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0,.0,]nonadeca-1(12),2,4,10-tetraen-15-yl acetic acid	Generator

Chemical Formula

C₃₄H₄₂O₉

Average Mass

594.7010 Da

Monoisotopic Mass

594.28288 Da

IUPAC Name

Traditional Name

(9R,13S,15R,16R,17R,18S)-18-(acetyloxy)-16-[(1R)-1-hydroxy-1-[(2S)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0^{3,9}.0^{13,17}]nonadeca-1(12),2,4,10-tetraen-15-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@]2(C)C3=C(C[C@H](OC(C)=O)[C@]2(C)[C@H]1[C@@](C)(O)[C@@H]1CC=C(C)C(=O)O1)C=C1C=CC(=O)OC(C)(C)[C@@H]1C=C3

InChI Identifier

InChI=1S/C34H42O9/c1-18-9-13-26(42-30(18)38)34(8,39)29-25(40-19(2)35)17-32(6)24-12-11-23-21(10-14-28(37)43-31(23,4)5)15-22(24)16-27(33(29,32)7)41-20(3)36/h9-12,14-15,23,25-27,29,39H,13,16-17H2,1-8H3/t23-,25-,26+,27+,29+,32+,33-,34+/m1/s1

InChI Key

OZGJHTKUIUKNKQ-MCFBLURZSA-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
Kadsura heteroclita	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Dihydropyranone
Pyran
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.11	ChemAxon
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	160.73 m³·mol⁻¹	ChemAxon
Polarizability	64.53 Å³	ChemAxon
Number of Rings	5	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

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

162877687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate (NP0303758)

MOL for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

3D MOL for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

3D SDF for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

3D-SDF for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

PDB for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

3D PDB for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

SMILES for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

INCHI for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

Structure for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)

3D Structure for NP0303758 ((9r,13s,15r,16r,17r,18s)-18-(acetyloxy)-16-[(1r)-1-hydroxy-1-[(2s)-5-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-8,8,13,17-tetramethyl-6-oxo-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4,10-tetraen-15-yl acetate)