NP-MRD: Showing NP-Card for 5alpha-cholest-22E-en-3-ol (NP0085721)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 06:12:07 UTC

Updated at

2022-04-29 06:12:07 UTC

NP-MRD ID

NP0085721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-cholest-22E-en-3-ol

Description

5Alpha-cholest-22E-en-3beta-ol, also known as 5α-cholest-22E-en-3β-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholest-22E-en-3beta-ol is considered to be a sterol. 5alpha-cholest-22E-en-3-ol is found in Amphilectus fucorum, Axinella aruensis, Axinella cannabina, Halocynthia aurantium, Hymeniacidon perlevis, Petrosia ficiformis, Phallusia nigra, Posidonia oceanica , Pyrocystis lunula and Salpa thompsoni. 5alpha-cholest-22E-en-3-ol was first documented in 2003 (PMID: 12822905). Based on a literature review very few articles have been published on 5alpha-cholest-22E-en-3beta-ol (PMID: 34142408).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208122D          

 33 36  0  0  1  0            999 V2000
    8.3674   -0.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5501   -0.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392    0.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5977    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1508    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9660   -0.9941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0438   -0.7875    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  1  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  1  0  0  0
  6 32  1  6  0  0  0
  2 33  1  0  0  0  0
M  END

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
    7.1444    1.1593    2.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2180    1.2490    1.3977 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8063    2.6689    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9170    0.4759    1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1043    0.6564    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6949   -0.3299   -0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8933   -0.1790   -1.5978 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7333   -0.7702   -2.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -0.8718   -1.6048 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6337   -2.3496   -1.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2355   -2.7124   -0.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5119   -1.4299   -0.9581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7260   -1.3097   -0.1346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7884   -2.2053   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1623   -1.9507   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4916   -0.4973   -0.1357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8618   -0.2092    0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1741    1.2520   -0.0034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.9889    1.8229    0.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8996    2.0504   -0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9269    1.6167    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183    0.2336    0.6705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1909   -0.4196    2.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1864    0.1441   -0.1658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1184    1.1099    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0170    0.9324   -0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -0.4330   -0.5937 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0297   -0.5561    0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6227    1.1351    3.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8563    0.3411    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7510    2.1084    2.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6934    0.7796    0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8887    2.9814    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6040    3.3941    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6387    2.7396   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1357   -0.6046    1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    0.8375    2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371    1.6707    0.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9764   -1.3363   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7260    0.8803   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165   -0.4355   -3.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -0.3315   -2.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578   -1.8749   -2.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1282   -0.6976   -2.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -2.9185   -2.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128   -2.6594   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -3.0275    0.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998   -3.5168   -1.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473   -1.2364   -2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508   -1.6662    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5029   -3.2577   -0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7261   -2.1155   -1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8725   -2.3774   -1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4407   -2.5128    0.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4023   -0.0676   -1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9890   -0.3482    1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5771   -0.8219   -0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7303    1.3222   -0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3490    2.6576    0.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156    3.1336    0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    1.9707   -1.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762    1.5568    1.8402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1743    2.3698    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563   -1.5043    2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9682   -0.0639    2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745   -0.0852    2.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877    0.3241   -1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4903    2.1270    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7634    0.9194    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277    1.0067   -1.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092    1.6934   -0.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.4810    1.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2047   -0.8458    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8398   -1.2726    1.0057 H   0  0  0  0  0  0  0  0  0  0  0  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  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
 27  9  1  0
 27 12  1  0
 24 13  1  0
 22 16  1  0
  9 44  1  6
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  6
 13 50  1  1
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  0
 17 57  1  0
 18 58  1  6
 19 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
  7 40  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
  6 39  1  0
  5 38  1  0
  4 36  1  0
  4 37  1  0
  2 32  1  6
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
M  END


  Mrv1652304292208122D          

 33 36  0  0  1  0            999 V2000
    8.3674   -0.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5501   -0.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2392    0.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4220    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111    1.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    1.6179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5977    0.8111    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1508    0.8481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584   -0.0730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -0.5585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9660   -0.9941    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830    2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0438   -0.7875    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  1  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  1  0  0  0
  6 32  1  6  0  0  0
  2 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085721

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8,18-25,28H,7,9-17H2,1-5H3/b8-6+/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
BWGQUGBECNWWDB-PNAUCWDRSA-N

> <FORMULA>
C27H46O

> <MOLECULAR_WEIGHT>
386.664

> <EXACT_MASS>
386.354866101

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.37967606137413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <ALOGPS_LOGP>
6.76

> <JCHEM_LOGP>
7.156546855333335

> <ALOGPS_LOGS>
-7.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491413656

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
120.8831

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      15.619  -0.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.094  -0.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.513   1.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.988   1.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.407   2.809   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0      10.449   1.514   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       5.882   1.583   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       3.842  -0.136   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       6.351  -1.043   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       1.803  -1.856   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.302   4.447   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.148  -1.470   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14   20   21                                             
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    7   11   19                                             
CONECT   19   18                                                            
CONECT   20   13                                                            
CONECT   21   13   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   23   14   31                                             
CONECT   31   30                                                            
CONECT   32    6                                                            
CONECT   33    2                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
5a-Cholest-22E-en-3b-ol	Generator
5Α-cholest-22E-en-3β-ol	Generator

Chemical Formula

C₂₇H₄₆O

Average Mass

386.6640 Da

Monoisotopic Mass

386.35487 Da

IUPAC Name

(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

Traditional Name

(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R,3E)-6-methylhept-3-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h6,8,18-25,28H,7,9-17H2,1-5H3/b8-6+/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

BWGQUGBECNWWDB-PNAUCWDRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Amphilectus fucorum	LOTUS Database	35616633
Axinella aruensis	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Halocynthia aurantium	LOTUS Database	35616633
Hymeniacidon perlevis	LOTUS Database	35616633
Petrosia ficiformis	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633
Posidonia oceanica	Plant	KNApSAcK
Pyrocystis lunula	LOTUS Database	35616633
Salpa thompsoni	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Cholesterol and derivatives (LMST01010099 )

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	6.76	ALOGPS
logP	7.16	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	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	4	ChemAxon
Refractivity	120.88 m³·mol⁻¹	ChemAxon
Polarizability	50.38 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

C00055693

Chemspider ID

4446758

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283666

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vandergrift SL, Elkins LC, Alves-de-Souza C, Leblond JD: First examination of sterols in the marine dinoflagellate genus Vulcanodinium. J Eukaryot Microbiol. 2021 Nov;68(6):e12863. doi: 10.1111/jeu.12863. Epub 2021 Jul 11. [PubMed:34142408 ]
Kaku K, Hiraga Y: Sterol composition of a cultured marine dinoflagellate, Heterocapsa circularisquama. Nat Prod Res. 2003 Aug;17(4):263-7. doi: 10.1080/1057563021000060130. [PubMed:12822905 ]

Showing NP-Card for 5alpha-cholest-22E-en-3-ol (NP0085721)

MOL for NP0085721 (5alpha-cholest-22E-en-3-ol)

3D MOL for NP0085721 (5alpha-cholest-22E-en-3-ol)

3D SDF for NP0085721 (5alpha-cholest-22E-en-3-ol)

3D-SDF for NP0085721 (5alpha-cholest-22E-en-3-ol)

PDB for NP0085721 (5alpha-cholest-22E-en-3-ol)

3D PDB for NP0085721 (5alpha-cholest-22E-en-3-ol)

SMILES for NP0085721 (5alpha-cholest-22E-en-3-ol)

INCHI for NP0085721 (5alpha-cholest-22E-en-3-ol)

Structure for NP0085721 (5alpha-cholest-22E-en-3-ol)

3D Structure for NP0085721 (5alpha-cholest-22E-en-3-ol)