NP-MRD: Showing NP-Card for 1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0260222)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 02:19:22 UTC

Updated at

2022-09-08 02:19:22 UTC

NP-MRD ID

NP0260222

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

14-(5-Ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-ol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Acacia auriculiformis, Agrobacterium rhizogenes, Ardisia brevicaulis, Argania spinosa, Aster ageratoides, Aster baccharoides, Aster koraiensis, Aster scaber, Axinella cannabina, Baccharis ochracea, Barringtonia asiatica, Bidens pilosa, Bupleurum aureum, Bupleurum longiradiatum, Camellia sinensis, Chondrilla nucula, Citrullus colocynthis, Conium maculatum, Conyza filaginoides, Conyza pyrrhopappa, Cucurbita maxima, Cucurbita pepo, Cyanidium caldarium, Diploknema butyracea, Erythrophleum fordii, Eschenbachia blinii, Grangea maderaspatana, Grindelia tarapacana, Harpullia arborea, Hibiscus sabdariffa, Hydrocotyle leucocephala, Hydrodictyon reticulatum, Hylomecon japonica, Impatiens balsamina, Juncus effusus, Lagenaria siceraria, Manilkara bidentata, Manilkara hexandra, Glinus oppositifolius, Momordica charantia, Myriactis humilis, Nigella sativa, Oocystis polymorpha, Phallusia nigra, Phytolacca americana, Pittosporum illicioides, Platycodon grandiflorus, Polygala cyparissias, Scrophularia smithii and Tephrosia purpurea. 14-(5-Ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514422D          

 30 33  0  0  0  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
    6.5577   -0.5497    2.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.0263    2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520   -0.8188    1.1064 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4448    0.1436    0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1752    0.5010   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.3985   -1.0070 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9052    2.6397   -1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    1.9540   -0.0754 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2940    2.9614   -0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683    3.1094   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1152    1.8908    0.6899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4528    1.2564    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337    1.4524    1.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7105    0.8978    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9067   -0.1921    0.5373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7788   -1.5549    1.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4903   -2.5612    0.3062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9016   -3.8084    0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4820   -2.0926   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -1.4624   -1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0922   -0.0680   -0.6894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8676    0.8165   -1.6843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7207    0.4311   -0.6085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6441   -0.6320   -0.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3345    0.1385   -0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0210    0.9720    0.2806 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2916    0.1186    1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2736   -1.3435   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4262   -2.2269    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3990   -2.1964   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6284   -0.1376    3.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5011   -0.1365    2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6382   -1.6240    2.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313    0.4823    2.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926    0.9811    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -1.5991    1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9245    0.5312    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    0.0952   -1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5869    0.9558   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7556    2.3217   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1958    3.2405   -0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2113    3.2179   -2.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4789    2.5017    0.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    3.9631   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283    2.6252   -1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9569    4.0133    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602    3.2352   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424    2.1482    1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0584    2.0875    2.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    0.5126    2.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4038    1.7496    1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9955   -0.1300    0.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3249   -1.5115    2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7152   -1.8211    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5367   -2.6362    0.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5403   -4.4784    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5575   -2.9527   -1.8501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3103   -1.4169   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.3418   -2.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4063   -2.1586   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5180    0.2393   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4709    1.5443   -1.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1766    1.4140   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5342    1.0950   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5053   -1.2118    0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7354   -1.3074   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4532   -0.6252   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335    0.7172   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7382   -0.2264    1.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7104    0.7647    2.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -0.8057    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5033   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3415   -1.6996    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0709   -2.9776    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -2.9225   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175   -2.1189   -0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6535   -3.2554   -0.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218   -2.0394   -2.0429 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  2  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  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  1
  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
  5 38  1  0
  6 39  1  6
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  1
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  0
 16 54  1  0
 17 55  1  1
 18 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  6
 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


  Mrv1533004161514422D          

 30 33  0  0  0  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7071   -2.6894    0.0000 C   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
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  8 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260222

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C=CC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)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/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3

> <INCHI_KEY>
JZVFJDZBLUFKCA-UHFFFAOYSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.299644912407764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <ALOGPS_LOGP>
7.46

> <JCHEM_LOGP>
7.482555135333334

> <ALOGPS_LOGS>
-7.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.361777845540015

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3283583703607977

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
130.88269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.40e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   12   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    8   11   27                                             
CONECT   27   26                                                            
CONECT   28    3   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
a-Spinasterol	Generator
Α-spinasterol	Generator
Spinasterol	MeSH
Spinasterol, (3beta,5alpha,22E,24R)-isomer	MeSH

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

Traditional Name

14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

CCC(C=CC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)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/h8-9,11,19-23,25-27,30H,7,10,12-18H2,1-6H3

InChI Key

JZVFJDZBLUFKCA-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
Acacia auriculiformis	LOTUS Database	35616633
Agrobacterium rhizogenes	LOTUS Database	35616633
Ardisia brevicaulis	LOTUS Database	35616633
Argania spinosa	LOTUS Database	35616633
Aster ageratoides	LOTUS Database	35616633
Aster baccharoides	LOTUS Database	35616633
Aster koraiensis	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Baccharis ochracea	LOTUS Database	35616633
Barringtonia asiatica	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Bupleurum aureum	LOTUS Database	35616633
Bupleurum longiradiatum	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Chondrilla nucula	LOTUS Database	35616633
Citrullus colocynthis	LOTUS Database	35616633
Conium maculatum	LOTUS Database	35616633
Conyza filaginoides	LOTUS Database	35616633
Conyza pyrrhopappa	LOTUS Database	35616633
Cucurbita maxima	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Cyanidium caldarium	LOTUS Database	35616633
Diploknema butyracea	LOTUS Database	35616633
Erythrophleum fordii	LOTUS Database	35616633
Eschenbachia blinii	LOTUS Database	35616633
Grangea maderaspatana	LOTUS Database	35616633
Grindelia tarapacana	LOTUS Database	35616633
Harpullia arborea	LOTUS Database	35616633
Hibiscus sabdariffa	LOTUS Database	35616633
Hydrocotyle leucocephala	LOTUS Database	35616633
Hydrodictyon reticulatum	LOTUS Database	35616633
Hylomecon japonica	LOTUS Database	35616633
Impatiens balsamina	LOTUS Database	35616633
Juncus effusus	LOTUS Database	35616633
Lagenaria siceraria	LOTUS Database	35616633
Manilkara bidentata	LOTUS Database	35616633
Manilkara hexandra	LOTUS Database	35616633
Mollugo oppositifolia	LOTUS Database	35616633
Momordica charantia	LOTUS Database	35616633
Myriactis humilis	LOTUS Database	35616633
Nigella sativa	LOTUS Database	35616633
Oocystis polymorpha	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Phytolacca americana	LOTUS Database	35616633
Pittosporum illicioides	LOTUS Database	35616633
Platycodon grandiflorus	LOTUS Database	35616633
Polygala cyparissias	LOTUS Database	35616633
Scrophularia smithii	LOTUS Database	35616633
Tephrosia purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	7.46	ALOGPS
logP	7.48	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.88 m³·mol⁻¹	ChemAxon
Polarizability	52.3 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	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

521229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0260222)

MOL for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0260222 (1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol)