NP-MRD: Showing NP-Card for (1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione (NP0273293)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 20:16:57 UTC

Updated at

2022-09-08 20:16:57 UTC

NP-MRD ID

NP0273293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione

Description

(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]Docosa-16,20-diene-8,13,18-trione belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton. (1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione is found in Citrullus colocynthis. Based on a literature review very few articles have been published on (1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]Docosa-16,20-diene-8,13,18-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222162D          

 38 42  0  0  1  0            999 V2000
   -1.9156   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -1.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207   -1.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -0.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262   -0.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0747    0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257    1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    1.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    1.2778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0496    2.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.6440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6125   -0.1641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3297   -0.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391   -0.0157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1992   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601   -0.0965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1007   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9217   -0.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    0.4933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5421    1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8437    1.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    0.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5248    0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2232   -0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8767   -0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711   -1.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    0.5741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7211    1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3806    1.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986    0.7357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1813    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771   -0.5380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 22 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 13 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  6  0  0  0
 14 38  1  0  0  0  0
  6 38  1  0  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
   -7.1619    0.0003    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5326   -0.8898    0.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3120   -1.3559    0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612   -1.9104   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2899   -2.7463    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1680   -0.5544    1.1118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2729    0.9124    1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9757    1.7128    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780    2.6516   -0.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    1.5193   -0.9731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4735    2.8990   -1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4493    0.7520   -1.9411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7558    0.8493   -0.1804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1157   -0.6031   -0.1041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7893   -1.3817    0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643   -0.2542    0.3098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1808    0.1306    1.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137   -0.5748    0.2145 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2613   -0.6470    1.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7240   -0.6722    1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553   -0.1377    0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8272    0.5392   -0.4400 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7200    0.5281   -1.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972   -0.0528   -1.6889 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6424   -0.0021   -2.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -0.7608   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2183   -1.7138   -0.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228   -0.1897    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4651    1.2434    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.9792    1.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4238    0.1223   -0.7946 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6417   -0.7851   -2.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7719    1.4205   -1.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3308    2.0464   -2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5272    1.9349   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810    0.7595   -0.6716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3714    0.3636   -2.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9538   -1.0647    0.7655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3245   -0.3642   -0.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2404    0.1212    0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7659    1.0080    0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3632   -1.1411   -1.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007   -2.4375   -0.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9365   -2.7302   -0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1207   -3.3336    1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2507   -2.5097    2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3369   -3.2203    1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1630   -0.8311    2.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    1.2153    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1880    1.2386    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4458    3.4358   -1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822    2.9690   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0410    3.4327   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7816    1.3751   -2.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.4108    0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -0.8555   -1.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202   -2.0531    0.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5572   -2.0132   -0.8078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1008    1.1365    2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2448   -0.6546    2.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2700   -0.0634    1.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6040   -1.6787   -0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559   -1.6011    2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0120    0.2645    2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2171   -1.1797    2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8318    1.6488   -0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3816    1.0288   -2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0136   -0.8302   -3.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7779    1.5919   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7264    1.8947    1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3487    1.2270    1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241   -1.9981    2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0485   -0.4261    2.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5197   -0.9228    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.3141   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -1.6445   -1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5525   -0.2419   -2.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7658    2.2595    0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995    2.8108   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886    0.6720   -2.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148    0.8920   -2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613   -0.6983   -2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  6
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 22 31  1  0
 31 32  1  6
 31 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  6
 14 38  1  0
 38  6  1  0
 36 13  1  0
 36 16  1  0
 31 18  1  0
 28 21  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  4 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  5 47  1  0
  6 48  1  1
  7 49  1  0
  7 50  1  0
 11 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  0
 13 55  1  1
 14 56  1  6
 15 57  1  0
 15 58  1  0
 17 59  1  0
 17 60  1  0
 17 61  1  0
 18 62  1  6
 19 63  1  0
 19 64  1  0
 20 65  1  0
 22 66  1  1
 23 67  1  0
 25 68  1  0
 29 69  1  0
 29 70  1  0
 29 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 32 75  1  0
 32 76  1  0
 32 77  1  0
 35 78  1  0
 35 79  1  0
 37 80  1  0
 37 81  1  0
 37 82  1  0
M  END


  Mrv1652309082222162D          

 38 42  0  0  1  0            999 V2000
   -1.9156   -0.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413   -1.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5075   -0.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0207   -1.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0357   -0.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1262   -0.1962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0747    0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257    1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518    1.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    1.2778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0496    2.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    1.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.6440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6125   -0.1641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3297   -0.5718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391   -0.0157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1992   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7601   -0.0965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1007   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9217   -0.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -0.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0617    0.4933    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5421    1.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3632    1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8437    1.7538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    0.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5248    0.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2232   -0.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8767   -0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711   -1.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    0.5741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7211    1.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3806    1.9962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986    0.7357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1813    1.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771   -0.5380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 22 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 13 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  6  0  0  0
 14 38  1  0  0  0  0
  6 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)[C@@H]1CC(=O)[C@](C)(O)[C@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](C=C(O)C(=O)C5(C)C)[C@]4(C)C(=O)C[C@]23C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O7/c1-26(2)16-10-11-20-28(5)14-19-24(31(8,36)21(33)13-23(38-19)27(3,4)37-9)29(28,6)15-22(34)30(20,7)17(16)12-18(32)25(26)35/h10,12,17,19-20,23-24,32,36H,11,13-15H2,1-9H3/t17-,19-,20+,23+,24+,28+,29-,30+,31+/m1/s1

> <INCHI_KEY>
KGYOQUPPUIDIOS-CJAZSQSXSA-N

> <FORMULA>
C31H44O7

> <MOLECULAR_WEIGHT>
528.686

> <EXACT_MASS>
528.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.71041957307606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

> <JCHEM_LOGP>
3.774294297333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.940018943930426

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.026430129810885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6955736084161854

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
144.9696

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.576  -1.807   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.130  -2.338   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.947  -1.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.039  -2.535   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.933  -0.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.236  -0.366   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.139   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.795   2.352   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.097   3.725   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.334   2.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.959   3.879   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.707   3.083   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.320   1.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.010  -0.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.349  -1.067   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.486  -0.029   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.972  -1.491   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.019  -0.180   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.655  -1.583   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.187  -1.734   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.084  -0.482   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.448   0.921   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.345   2.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.878   2.022   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.775   3.274   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.514   0.619   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.046   0.468   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.617  -0.633   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.836  -1.573   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.519  -2.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.916   1.072   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.813   2.323   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.280   2.474   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.177   3.726   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.748   2.625   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.851   1.373   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.072   2.702   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.637  -1.004   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   38                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   36                                                  
CONECT   14   13   15   38                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   36                                             
CONECT   17   16                                                            
CONECT   18   16   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   22   18   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   13   16   37                                             
CONECT   37   36                                                            
CONECT   38   14    6                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₄O₇

Average Mass

528.6860 Da

Monoisotopic Mass

528.30870 Da

IUPAC Name

(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

Traditional Name

(1S,2S,4R,6S,9R,10R,11R,14R,15R)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0^{2,11}.0^{4,10}.0^{15,20}]docosa-16,20-diene-8,13,18-trione

CAS Registry Number

Not Available

SMILES

COC(C)(C)[C@@H]1CC(=O)[C@](C)(O)[C@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](C=C(O)C(=O)C5(C)C)[C@]4(C)C(=O)C[C@]23C)O1

InChI Identifier

InChI=1S/C31H44O7/c1-26(2)16-10-11-20-28(5)14-19-24(31(8,36)21(33)13-23(38-19)27(3,4)37-9)29(28,6)15-22(34)30(20,7)17(16)12-18(32)25(26)35/h10,12,17,19-20,23-24,32,36H,11,13-15H2,1-9H3/t17-,19-,20+,23+,24+,28+,29-,30+,31+/m1/s1

InChI Key

KGYOQUPPUIDIOS-CJAZSQSXSA-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
Citrullus colocynthis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

11-oxosteroids

Alternative Parents

Substituents

20-hydroxysteroid
3-oxo-delta-1-steroid
3-oxosteroid
14-alpha-methylsteroid
2-hydroxysteroid
11-oxosteroid
Hydroxysteroid
Delta-1-steroid
Cyclohexenone
Oxepane
Acyloin
Tertiary alcohol
Cyclic ketone
Ketone
Organoheterocyclic compound
Ether
Enol
Dialkyl ether
Oxacycle
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.77	ChemAxon
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.97 m³·mol⁻¹	ChemAxon
Polarizability	58.71 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	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

162902531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione (NP0273293)

MOL for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

3D MOL for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

3D SDF for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

3D-SDF for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

PDB for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

3D PDB for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

SMILES for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

INCHI for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

Structure for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)

3D Structure for NP0273293 ((1s,2s,4r,6s,9r,10r,11r,14r,15r)-9,17-dihydroxy-6-(2-methoxypropan-2-yl)-2,9,11,14,19,19-hexamethyl-5-oxapentacyclo[12.8.0.0²,¹¹.0⁴,¹⁰.0¹⁵,²⁰]docosa-16,20-diene-8,13,18-trione)