NP-MRD: Showing NP-Card for 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0208576)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 05:37:58 UTC

Updated at

2022-09-05 05:37:58 UTC

NP-MRD ID

NP0208576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one

Description

2-Deoxycastasterone, also known as typhasterol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 2-Deoxycastasterone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-deoxycastasterone is found, on average, in the highest concentration in corns. 2-Deoxycastasterone has also been detected, but not quantified in, several different foods, such as highbush blueberries, roselles, grapefruit/pummelo hybrids, common grapes, and lima beans. 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one is found in Arabidopsis thaliana, Camellia sinensis, Erythronium japonicum, Raphanus sativus, Senna tora and Typha capensis. This could make 2-deoxycastasterone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307482D          

 32 35  0  0  0  0            999 V2000
    1.6892   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -6.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -4.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615   -6.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -6.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5985   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0622   -4.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692   -4.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2125   -7.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7916   -6.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4055   -7.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9846   -6.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5096   -5.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6407   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7645   -6.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0887   -5.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9760   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -5.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3436   -6.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7026   -5.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4477   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297   -5.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1506   -6.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5715   -6.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997   -4.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -6.6905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -4.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 15  1  0  0  0  0
 17  4  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 11  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 18  1  0  0  0  0
 30 24  2  0  0  0  0
 31 25  1  0  0  0  0
 32 26  1  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
    8.3943    0.9557    0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748    0.2794   -0.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9599    0.7370   -1.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9367    0.5384    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2126   -0.0212    2.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7693   -0.1155   -0.0308 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0053   -1.4747   -0.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4514    0.2446    0.6305 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4520    1.6648    0.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650   -0.3146   -0.1170 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3909   -1.7903   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.2362    0.3655 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9133    1.7142    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5499    2.0358    0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981    0.8358   -0.3512 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5724    0.6633    0.2621 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3880    1.8312   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7670    1.6474    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5636    2.5452   -0.0212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077    0.3964    0.7793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6988    0.3362    0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2298    0.3251   -0.6634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.3201   -0.5657   -0.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1858   -0.1106   -1.6547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3338   -1.2328   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5865   -0.8368    0.1447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8381   -1.9767    1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205   -0.6505   -0.1624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2677   -1.7307    0.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -1.1930    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -0.3323   -0.1292 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1890   -1.0874   -1.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9620    0.2821    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1122    1.8759    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0679    1.2971   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3549   -0.8038   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6664   -0.1034   -2.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    1.1331   -2.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2189    1.5673   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7406    1.6244    0.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1040   -1.1094    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2587    0.2156    2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5605    0.5054    2.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7554    0.2715   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4529   -1.7300   -0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5167   -0.0583    1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403    2.0331   -0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986    0.0550   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   -2.1064    0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0184   -2.1527   -1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4567   -2.3722   -0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938    0.0745    1.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935    2.2492    1.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110    2.0360   -0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    2.1094    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    2.9821   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3756    1.0300   -1.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691    0.8399    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2574    1.8109   -1.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284    2.7540    0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8734    0.4464    1.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0675    1.3010    1.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1446   -0.4567    1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6193    1.3070   -1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6718   -0.5596   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7449   -0.5461   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5918    0.7178   -2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9700   -2.1107   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910   -1.4788   -1.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728   -2.9485    0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9637   -2.0969    1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5848   -1.7332    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9876   -0.7462   -1.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7386   -2.1330    1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1282   -2.6032   -0.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -2.0183    1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437   -0.5325    1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8327   -0.5671   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5465   -2.1162   -1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8322   -0.9894   -1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31 12  1  0
 31 15  1  0
 28 16  1  0
 26 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  6
  7 45  1  0
  8 46  1  1
  9 47  1  0
 10 48  1  6
 11 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 15 57  1  6
 16 58  1  1
 17 59  1  0
 17 60  1  0
 20 61  1  1
 21 62  1  0
 21 63  1  0
 22 64  1  6
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  6
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
M  END


  Mrv0541 05061307482D          

 32 35  0  0  0  0            999 V2000
    1.6892   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -6.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -4.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615   -6.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -6.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5985   -6.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0622   -4.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8692   -4.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2125   -7.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7916   -6.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4055   -7.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9846   -6.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5096   -5.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6407   -4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2615   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7645   -6.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0887   -5.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9760   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2817   -5.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3436   -6.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7026   -5.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4477   -4.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297   -5.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1506   -6.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5715   -6.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997   -4.2923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326   -6.6905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -4.6280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 15  1  0  0  0  0
 17  4  1  0  0  0  0
 18  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20  7  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27  5  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 11  1  0  0  0  0
 28 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 18  1  0  0  0  0
 30 24  2  0  0  0  0
 31 25  1  0  0  0  0
 32 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(O)CCC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-23,25-26,29,31-32H,7-14H2,1-6H3

> <INCHI_KEY>
SBSXXCCMIWEPEE-UHFFFAOYSA-N

> <FORMULA>
C28H48O4

> <MOLECULAR_WEIGHT>
448.6783

> <EXACT_MASS>
448.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
54.37517521420305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
4.576522391

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.861077440618988

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.644363838141157

> <JCHEM_PKA_STRONGEST_BASIC>
-2.696313461282922

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
127.85939999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.153 -10.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.487 -12.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.820  -8.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.821 -12.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.418 -11.836   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.051 -12.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.316  -8.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.823  -8.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.063 -13.551   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.544 -12.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.557 -13.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.038 -12.270   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.618 -10.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.129  -8.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.487 -10.949   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.820 -10.179   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.821 -10.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.094 -12.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.099  -9.981   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.155 -10.179   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.593  -9.661   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.575 -11.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.112 -10.621   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.636  -9.157   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.154 -10.949   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.488 -10.179   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.562 -10.805   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.081 -11.766   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      21.600 -12.726   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      18.666  -8.012   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.154 -12.489   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.488  -8.639   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7    8   20                                                       
CONECT    8    7   21                                                       
CONECT    9   11   18                                                       
CONECT   10   12   22                                                       
CONECT   11    9   28                                                       
CONECT   12   10   27                                                       
CONECT   13   18   23                                                       
CONECT   14   19   24                                                       
CONECT   15    1    2   16                                                  
CONECT   16    3   15   25                                                  
CONECT   17    4   20   26                                                  
CONECT   18    9   13   29                                                  
CONECT   19   14   21   22                                                  
CONECT   20    7   17   27                                                  
CONECT   21    8   19   27                                                  
CONECT   22   10   19   28                                                  
CONECT   23   13   24   28                                                  
CONECT   24   14   23   30                                                  
CONECT   25   16   26   31                                                  
CONECT   26   17   25   32                                                  
CONECT   27    5   12   20   21                                             
CONECT   28    6   11   22   23                                             
CONECT   29   18                                                            
CONECT   30   24                                                            
CONECT   31   25                                                            
CONECT   32   26                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Typhasterol	HMDB

Chemical Formula

C₂₈H₄₈O₄

Average Mass

448.6783 Da

Monoisotopic Mass

448.35526 Da

IUPAC Name

14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

Traditional Name

14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

CAS Registry Number

Not Available

SMILES

CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(O)CCC4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H48O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-23,25-26,29,31-32H,7-14H2,1-6H3

InChI Key

SBSXXCCMIWEPEE-UHFFFAOYSA-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
Arabidopsis thaliana	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Erythronium japonicum	LOTUS Database	35616633
Raphanus sativus	LOTUS Database	35616633
Senna tora	LOTUS Database	35616633
Typha capensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Ergostane-skeleton
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
22-hydroxysteroid
3-hydroxysteroid
6-oxosteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a brassinosteroids (CPD-719 )

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	3.73	ALOGPS
logP	4.58	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.86 m³·mol⁻¹	ChemAxon
Polarizability	54.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034423

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13475117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one (NP0208576)

MOL for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D MOL for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D SDF for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D-SDF for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

PDB for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D PDB for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

SMILES for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

INCHI for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

Structure for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)

3D Structure for NP0208576 (1-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-5-one)