NP-MRD: Showing NP-Card for (3β,5α)-stigmast-7-en-3-ol (NP0309479)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 04:06:41 UTC

Updated at

2022-09-11 04:06:41 UTC

NP-MRD ID

NP0309479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3β,5α)-stigmast-7-en-3-ol

Description

Schottenol, also known as 7-stigmastenol, 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. Thus, schottenol is considered to be a sterol. (3β,5α)-stigmast-7-en-3-ol is found in Arenaria kansuensis, Argania spinosa, Axinella cannabina, Baccharoides anthelmintica, Bidens pilosa, Brucea javanica, Bryonia dioica, Campanula medium, Carthamus tinctorius, Conium maculatum, Cucurbita maxima, Cyanidium caldarium, Kalanchoe marmorata, Lagenaria siceraria, Salvia sylvestris, Tetragonia tetragonoides and Zea mays. (3β,5α)-stigmast-7-en-3-ol was first documented in 2014 (PMID: 24582563). Based on a literature review a small amount of articles have been published on Schottenol (PMID: 32422925) (PMID: 29065513) (PMID: 25595450).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206062D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4739    1.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9885    3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    3.8850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9446    4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862    3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    2.2711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0432    1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2585    1.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8716    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  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  1  0  0  0
 21 23  1  0  0  0  0
 23 12  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  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

 80 83  0  0  0  0  0  0  0  0999 V2000
   -7.1985    2.0605   -0.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1500    0.8945    0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9794   -0.0581    0.5015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6856    0.6581    0.6850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -0.1722    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864    0.6607    0.7610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2586    1.1886    2.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2210    0.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2714   -0.5736   -1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187   -0.4066   -1.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809   -0.6386   -0.5669 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4071   -0.3022   -0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9027    0.1312   -1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3437    0.4628   -1.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1130   -0.4296   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6064   -0.2171   -1.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3336   -1.2059   -0.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6981   -0.9407   -0.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151   -1.2650    1.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390   -1.4777    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6401   -0.3322    0.3814 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0868    0.9413    1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1913   -0.5117    0.5319 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5278    0.3532    1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0697   -0.0965    1.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181    0.2751    0.4914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5226    1.7015    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1517   -0.8740   -0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1879   -0.1185   -2.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3979   -2.1604   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1520    2.0077   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3734    3.0203    0.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3553    2.1922   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0825    0.2678    0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1634    1.2467    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0887   -0.7835    1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733    1.2761    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    1.4362   -0.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4079   -0.9522    1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934   -0.6950   -0.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    1.5181    0.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7152    0.5143    2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840    1.6276    2.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238    2.1063    2.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421   -1.1703    0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -1.6286   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784    0.1206   -1.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2481   -1.1110   -2.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1524    0.6294   -2.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.6779   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    0.2558   -2.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5487    1.5342   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.2710   -3.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9198   -1.4885   -1.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8656   -0.4370   -2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9059    0.8288   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2157   -2.2178   -0.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8650    0.0067   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1532   -0.4094    1.7080 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907   -2.1772    1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9784   -1.5589    2.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1200   -2.4117    0.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063    0.7622    2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575    1.1724    0.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5134    1.8258    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -1.5729    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0383    0.3029    2.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694    1.3794    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224    0.4062    2.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0741   -1.2003    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3556    2.0220   -0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7040    2.3859    0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4099    1.8458   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2728   -1.2298   -0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3034    0.5299   -2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1481    0.3653   -2.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1112   -0.8985   -2.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1235   -2.9955   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6685   -2.2118   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9341   -2.3556    0.1963 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  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  1
 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
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  6
 16 55  1  0
 16 56  1  0
 17 57  1  6
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 24 68  1  0
 25 69  1  0
 25 70  1  0
 27 71  1  0
 27 72  1  0
 27 73  1  0
 28 74  1  0
 29 75  1  0
 29 76  1  0
 29 77  1  0
 30 78  1  0
 30 79  1  0
 30 80  1  0
M  END


  Mrv1652309112206062D          

 30 33  0  0  1  0            999 V2000
    8.2924   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -0.9035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2299   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8174   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -1.6180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5799   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7594   -0.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879   -0.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024    0.4022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4739    1.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323    2.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170    2.8231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9885    3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731    3.8850    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9446    4.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3862    3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2147    2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4301    2.2711    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0432    1.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2585    1.4641    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8716    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7001    0.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.1499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4675   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4674   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2924   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0549   -2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  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  1  0  0  0
 21 23  1  0  0  0  0
 23 12  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
  8 26  1  0  0  0  0
 26 27  1  1  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>
NP0309479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O/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/h11,19-23,25-27,30H,7-10,12-18H2,1-6H3/t20-,21-,22+,23+,25-,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
YSKVBPGQYRAUQO-UZSYLJJSSA-N

> <FORMULA>
C29H50O

> <MOLECULAR_WEIGHT>
414.718

> <EXACT_MASS>
414.38616623

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.15142437338308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_LOGP>
7.844476792000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <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>
129.76609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      15.479  -0.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.939  -0.353   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.169  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.629  -1.687   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.859  -3.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.319  -3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.549  -4.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.549  -1.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.018  -1.526   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.697  -0.019   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.031   0.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.351   2.257   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.207   3.288   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.527   4.794   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.992   5.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.312   6.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.776   7.252   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.097   8.758   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.921   6.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.601   4.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.136   4.239   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.281   3.209   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.816   2.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.960   1.702   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.640   0.196   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.176  -0.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.206  -1.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.939  -3.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.479  -3.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.169  -4.354   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   11    8   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
7-Stigmastenol	Kegg
(3beta,5alpha)-Stigmast-7-en-3-ol	Kegg
(3b,5a)-Stigmast-7-en-3-ol	Generator
(3Β,5α)-stigmast-7-en-3-ol	Generator
Stigmast-7-en-3-ol	MeSH
22,23-Dihydrospinasterol	MeSH
Stigmast-7-enol, (3beta,5alpha)-isomer	MeSH
delta(7)-Stigmastenol	MeSH
Stigmast-7-enol, (3beta,5alpha,24S)-isomer	MeSH
Stigmast-7-enol	MeSH

Chemical Formula

C₂₉H₅₀O

Average Mass

414.7180 Da

Monoisotopic Mass

414.38617 Da

IUPAC Name

(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

Traditional Name

(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol

CAS Registry Number

Not Available

SMILES

CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

InChI Identifier

InChI=1S/C29H50O/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/h11,19-23,25-27,30H,7-10,12-18H2,1-6H3/t20-,21-,22+,23+,25-,26+,27+,28+,29-/m1/s1

InChI Key

YSKVBPGQYRAUQO-UZSYLJJSSA-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
Arenaria kansuensis	LOTUS Database	35616633
Argania spinosa	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Baccharoides anthelmintica	LOTUS Database	35616633
Bidens pilosa	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Bryonia dioica	LOTUS Database	35616633
Campanula medium	LOTUS Database	35616633
Carthamus tinctorius	LOTUS Database	35616633
Conium maculatum	LOTUS Database	35616633
Cucurbita maxima	LOTUS Database	35616633
Cyanidium caldarium	LOTUS Database	35616633
Kalanchoe marmorata	LOTUS Database	35616633
Lagenaria siceraria	LOTUS Database	35616633
Salvia x sylvestris	LOTUS Database	35616633
Tetragonia tetragonioides	LOTUS Database	35616633
Zea mays	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
3-beta-hydroxysteroid
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

steroid (CHEBI:9049 )
stigmastane (C08839 )
Stigmasterols and C24-ethyl derivatives (LMST01040133 )

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	7.84	ChemAxon
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	6	ChemAxon
Refractivity	129.77 m³·mol⁻¹	ChemAxon
Polarizability	54.15 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003671

Chemspider ID

390414

KEGG Compound ID

C08839

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rocchetti G, Rizzi C, Pasini G, Lucini L, Giuberti G, Simonato B: Effect of Moringa oleifera L. Leaf Powder Addition on the Phenolic Bioaccessibility and on In Vitro Starch Digestibility of Durum Wheat Fresh Pasta. Foods. 2020 May 14;9(5):628. doi: 10.3390/foods9050628. [PubMed:32422925 ]
Badreddine A, Zarrouk A, Karym EM, Debbabi M, Nury T, Meddeb W, Sghaier R, Bezine M, Vejux A, Martine L, Gregoire S, Bretillon L, Prost-Camus E, Durand P, Prost M, Moreau T, Cherkaoui-Malki M, Nasser B, Lizard G: Argan Oil-Mediated Attenuation of Organelle Dysfunction, Oxidative Stress and Cell Death Induced by 7-Ketocholesterol in Murine Oligodendrocytes 158N. Int J Mol Sci. 2017 Oct 23;18(10):2220. doi: 10.3390/ijms18102220. [PubMed:29065513 ]
Badreddine A, Karym el M, Zarrouk A, Nury T, El Kharrassi Y, Nasser B, Cherkaoui Malki M, Lizard G, Samadi M: An expeditious synthesis of spinasterol and schottenol, two phytosterols present in argan oil and in cactus pear seed oil, and evaluation of their biological activities on cells of the central nervous system. Steroids. 2015 Jul;99(Pt B):119-24. doi: 10.1016/j.steroids.2015.01.005. Epub 2015 Jan 13. [PubMed:25595450 ]
El Kharrassi Y, Samadi M, Lopez T, Nury T, El Kebbaj R, Andreoletti P, El Hajj HI, Vamecq J, Moustaid K, Latruffe N, El Kebbaj MS, Masson D, Lizard G, Nasser B, Cherkaoui-Malki M: Biological activities of Schottenol and Spinasterol, two natural phytosterols present in argan oil and in cactus pear seed oil, on murine miroglial BV2 cells. Biochem Biophys Res Commun. 2014 Apr 11;446(3):798-804. doi: 10.1016/j.bbrc.2014.02.074. Epub 2014 Feb 25. [PubMed:24582563 ]
LOTUS database [Link]

Showing NP-Card for (3β,5α)-stigmast-7-en-3-ol (NP0309479)

MOL for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

3D MOL for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

3D SDF for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

3D-SDF for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

PDB for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

3D PDB for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

SMILES for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

INCHI for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

Structure for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)

3D Structure for NP0309479 ((3β,5α)-stigmast-7-en-3-ol)