NP-MRD: Showing NP-Card for Sitostenone (NP0137437)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-30 16:52:27 UTC

Updated at

2022-05-30 16:52:27 UTC

NP-MRD ID

NP0137437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sitostenone

Description

Ammonia, also known as NH3 or amoniaco, belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'. An Ammonia that consists of a single nitrogen atom covelently bonded to three hydrogen atoms. Ammonia is a drug. Ammonia is a very strong basic compound (based on its pKa). Ammonia exists in all living species, ranging from bacteria to humans. In humans, ammonia is involved in the metabolic disorder called hawkinsinuria. Ammonia is an ammoniacal tasting compound. Outside of the human body, Ammonia is found, on average, in the highest concentration within a few different foods, such as soy beans, barley, and white cabbages and in a lower concentration in tea, green bell peppers, and orange bell peppers. Ammonia has also been detected, but not quantified in, several different foods, such as corn salad, other bread, rocket salad (ssp.), Acorns, and sourdoughs. This could make ammonia a potential biomarker for the consumption of these foods. Ammonia is a potentially toxic compound. Sitostenone is found in Aleurites moluccanus, Alsophila gigantea, Annona montana, Casearia membranacea, Cinnamomum tenuifolium, Corymbia citriodora, Croton lechleri, Euphorbia portlandica, Garcinia multiflora, Harrisonia abyssinica, Herbertus aduncus, Lindera glauca, Melaleuca leucadendra, Microtropis fokienensis, Neolitsea sericea, Piper sintenense, Plenckia populnea, Prunus africana, Senna multijuga, Sideritis cretica, Torreya jackii, Xylopia vielana, Zanthoxylum simulans and Zanthoxylum wutaiense. Sitostenone was first documented in 1995 (PMID: 11540049). Ammonia, with regard to humans, has been found to be associated with several diseases such as citrullinemia type II, adult-onset, mitochondrial trifunctional protein deficiency, and phosphoenolpyruvate carboxykinase deficiency 1, cytosolic; ammonia has also been linked to several inborn metabolic disorders including citrullinemia type I and n-acetylglutamate synthetase deficiency (PMID: 11139349) (PMID: 11746427) (PMID: 11783653).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241221522D          

 30 33  0  0  0  0            999 V2000
   -3.3995   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.0096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9706   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    0.2279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5417   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8285   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    1.4654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6017    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    1.8779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0307    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    2.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
    8.0909   -0.4969   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -0.7196   -0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6510   -0.3576    0.1225 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3429   -0.6348   -0.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -0.3735    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945   -0.7787   -0.6432 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0696   -2.2135   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7097   -0.3044    0.0625 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4454   -0.8485    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9044   -0.1869    1.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061    0.5823    0.5198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7409    0.7851    0.3251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3080    1.3540    1.6255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6263    2.0161    1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4384    1.0950    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7569    1.3420    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6392    0.4858   -0.4511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6845    0.9791   -0.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2580   -0.9265   -0.6479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8834   -1.2233   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9380   -0.0649   -0.3301 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9577    0.1929   -1.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5366   -0.4568    0.0245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8370   -1.1814   -1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4144   -1.5233   -0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6229   -0.2796   -0.5695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6886    0.5496   -1.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8801    1.0230    0.6181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9820    1.5243    1.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8258    2.0408   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7438   -1.3174   -0.8316 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1106   -0.6164    0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5529    0.4441   -0.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5644   -1.7742   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5067   -0.0492   -1.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -1.0606    0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578   -0.0787   -1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -1.7351   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    0.7349    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -0.9017    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0579   -0.2002   -1.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7027   -2.3146   -1.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -2.7992   -1.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -2.7161   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9260    0.8094    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -1.9427    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -0.5227    2.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    0.5766    2.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6450   -0.9035    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7751    1.5418    0.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276    1.5274   -0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5187    0.5576    2.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    2.1066    1.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1044    2.3592    2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3330    2.8667    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1742    2.2026    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9987   -1.5490   -0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3511   -1.1769   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0090   -1.2835    1.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5255   -2.1743   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1343    0.9001   -2.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8570   -0.7909   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8886    0.6442   -2.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716   -1.1301    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3488   -2.1663   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410   -0.6758   -2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -2.3064   -1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051   -1.9706    0.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3553    1.4315   -1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441    0.9776   -1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9848   -0.0126   -2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9433    1.0799    0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3178    2.3813    1.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6426    1.9857    2.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4368    0.7364    2.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910    1.8984   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7352    3.0383   -0.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7373    1.9686   -1.1452 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
  3 28  1  0
 28 29  1  0
 28 30  1  0
 26  8  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  6
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  1
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  1
 12 51  1  6
 13 52  1  0
 13 53  1  0
 14 54  1  0
 14 55  1  0
 16 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  1
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 30 78  1  0
M  END


  Mrv0541 02241221522D          

 30 33  0  0  0  0            999 V2000
   -3.3995   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -1.0096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9706   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706   -2.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561   -1.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2561    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    0.2279    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5417   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    0.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8285   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851   -0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    1.4654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6017    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    1.8779    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0307    1.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    0.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5417    1.8779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162    2.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    3.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7  6  1  0  0  0  0
  6 19  1  1  0  0  0
 12  7  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 22 13  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 28  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24?,25?,26?,27?,28+,29-/m1/s1

> <INCHI_KEY>
RUVUHIUYGJBLGI-AXAJWWPKSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.6908

> <EXACT_MASS>
412.370516158

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
52.86690421608813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
6.95

> <JCHEM_LOGP>
8.411722740000002

> <ALOGPS_LOGS>
-7.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.087826253912493

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817440235063846

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
128.71469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.346  -1.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.679  -1.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.679  -3.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.346  -4.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.012  -3.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.012  -1.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.678  -1.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.678  -4.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.345  -3.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.345  -1.885   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.345   1.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.678   0.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.323   1.195   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.011   0.425   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.011  -1.115   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.656  -1.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.656   0.425   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.013  -4.195   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.012  -0.345   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.011   1.965   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.656   3.505   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.323   2.735   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.990   2.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.324   3.505   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.657   2.735   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.991   3.505   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.657   1.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.011   3.505   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.324   5.045   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.657   5.815   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7   19                                             
CONECT    7    6   12   10                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   15                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   22   17                                                  
CONECT   14   11   13   15   20                                             
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   13   16                                                       
CONECT   18    3                                                            
CONECT   19    6                                                            
CONECT   20   14                                                            
CONECT   21   22   23                                                       
CONECT   22   13   21   28                                                  
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22                                                            
CONECT   29   24   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
[NH3]	ChEBI
Ammoniac	ChEBI
Ammoniak	ChEBI
Amoniaco	ChEBI
NH3	ChEBI
R-717	ChEBI
Spirit OF hartshorn	ChEBI
Ammonia anhydrous	HMDB
Ammonia inhalant	HMDB
Ammonia solution strong	HMDB
Ammonia water	HMDB
Liquid ammonia	HMDB
Am-fol	HMDB
Ammonia (CONC 20% or greater)	HMDB
Ammonia gas	HMDB
Ammonia solution	HMDB
Ammonia solution strong (NF)	HMDB
Ammonia water (JP15)	HMDB
Ammoniacum gummi	HMDB
Ammoniak kconzentrierter	HMDB
Ammoniakgas	HMDB
Ammonium ion	HMDB
Anhydrous ammonia	HMDB
Aromatic ammonia vaporole	HMDB
Azane	HMDB
NH(3)	HMDB
Nitro-sil	HMDB
Primaeres amin	HMDB
Sekundaeres amin	HMDB
Tertiaeres amin	HMDB
4-Stigmasten-3-one	HMDB
b-Sitostenone	HMDB, Generator
laquo deltaraquo 4-Sitosterol-3-one	HMDB
Sitost-4-en-3-one	HMDB
Sitostenone	HMDB
Β-sitostenone	Generator

Chemical Formula

C₂₉H₄₈O

Average Mass

412.6908 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

(2R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)C1CCC2C3CCC4=CC(=O)CC[C@]4(C)C3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h18-21,24-27H,7-17H2,1-6H3/t20-,21-,24?,25?,26?,27?,28+,29-/m1/s1

InChI Key

RUVUHIUYGJBLGI-AXAJWWPKSA-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
Aleurites moluccanus	LOTUS Database	35616633
Alsophila gigantea	LOTUS Database	35616633
Annona montana	LOTUS Database	35616633
Casearia membranacea	LOTUS Database	35616633
Cinnamomum tenuifolium	LOTUS Database	35616633
Corymbia citriodora	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Euphorbia portlandica	LOTUS Database	35616633
Garcinia multiflora	LOTUS Database	35616633
Harrisonia abyssinica	LOTUS Database	35616633
Herbertus aduncus	LOTUS Database	35616633
Lindera glauca	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Microtropis fokienensis	LOTUS Database	35616633
Neolitsea sericea	LOTUS Database	35616633
Piper sintenense	LOTUS Database	35616633
Plenckia populnea	LOTUS Database	35616633
Prunus africana	LOTUS Database	35616633
Senna multijuga	LOTUS Database	35616633
Sideritis cretica	LOTUS Database	35616633
Torreya jackii	LOTUS Database	35616633
Xylopia vielana	LOTUS Database	35616633
Zanthoxylum simulans	LOTUS Database	35616633
Zanthoxylum wutaiense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.

Kingdom

Inorganic compounds

Super Class

Homogeneous non-metal compounds

Class

Homogeneous other non-metal compounds

Sub Class

Not Available

Direct Parent

Homogeneous other non-metal compounds

Alternative Parents

Not Available

Substituents

Homogeneous other non metal

Molecular Framework

Not Available

External Descriptors

mononuclear parent hydride (CHEBI:16134 )
azane (CHEBI:16134 )
a small molecule (AMMONIA )

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	6.95	ALOGPS
logP	8.41	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.71 m³·mol⁻¹	ChemAxon
Polarizability	52.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000051

DrugBank ID

DBMET01482

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Ammonia

METLIN ID

3189

PubChem Compound

222

PDB ID

Not Available

ChEBI ID

16134

Good Scents ID

Not Available

References

General References

Blei AT: Diagnosis and treatment of hepatic encephalopathy. Baillieres Best Pract Res Clin Gastroenterol. 2000 Dec;14(6):959-74. doi: 10.1053/bega.2000.0141. [PubMed:11139349 ]
Fox SW: Thermal synthesis of amino acids and the origin of life. Geochim Cosmochim Acta. 1995 Mar;59(6):1213-4. doi: 10.1016/0016-7037(95)00037-z. [PubMed:11540049 ]
Bai G, Rama Rao KV, Murthy CR, Panickar KS, Jayakumar AR, Norenberg MD: Ammonia induces the mitochondrial permeability transition in primary cultures of rat astrocytes. J Neurosci Res. 2001 Dec 1;66(5):981-91. doi: 10.1002/jnr.10056. [PubMed:11746427 ]
Baum MM, Kiyomiya ES, Kumar S, Lappas AM, Kapinus VA, Lord HC 3rd: Multicomponent remote sensing of vehicle exhaust by dispersive absorption spectroscopy. 2. Direct on-road ammonia measurements. Environ Sci Technol. 2001 Sep 15;35(18):3735-41. doi: 10.1021/es002046y. [PubMed:11783653 ]

Showing NP-Card for Sitostenone (NP0137437)

MOL for NP0137437 (Sitostenone)

3D MOL for NP0137437 (Sitostenone)

3D SDF for NP0137437 (Sitostenone)

3D-SDF for NP0137437 (Sitostenone)

PDB for NP0137437 (Sitostenone)

3D PDB for NP0137437 (Sitostenone)

SMILES for NP0137437 (Sitostenone)

INCHI for NP0137437 (Sitostenone)

Structure for NP0137437 (Sitostenone)

3D Structure for NP0137437 (Sitostenone)