NP-MRD: Showing NP-Card for 8-Dehydrocholesterol (NP0086845)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:32:37 UTC

Updated at

2022-05-11 16:32:37 UTC

NP-MRD ID

NP0086845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Dehydrocholesterol

Description

8-Dehydrocholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 8-dehydrocholesterol is considered to be a sterol lipid molecule. 8-Dehydrocholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In humans, 8-dehydrocholesterol is involved in the metabolic disorder called the child syndrome pathway. 8-Dehydrocholesterol is a potentially toxic compound. 8-Dehydrocholesterol was first documented in 1997 (PMID: 9266395). 8-Dehydrocholesterol (8-DHC) elevated concentration is one of the diagnostic biochemical hallmarks of classical Smith-Lemli-Opitz syndrome (SLOS) (PMID: 16435228) (PMID: 16761297) (PMID: 16231320).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219192D          

 30 33  0  0  1  0            999 V2000
   14.6941  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6941  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4085  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -11.2557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4085  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2664  -10.8431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2664  -10.0181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5519   -9.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511  -11.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5361  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511   -9.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9795  -12.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527   -9.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3061   -8.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1230  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527  -11.6636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7540   -8.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1130   -8.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3679   -8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -7.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4299   -7.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2369   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8778   -6.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8275   -9.6250    0.0000 H   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
  5 21  1  1  0  0  0
 11 22  1  6  0  0  0
 20 23  1  6  0  0  0
 24 20  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 27  1  0  0  0  0
 17 30  1  6  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
    6.5142    1.4129    2.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282    0.3520    1.5801 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5760   -1.0147    2.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652    0.3630    1.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -0.7465    0.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153   -0.8692   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    0.3579   -1.0780 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6277    0.8189   -2.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3463    0.3084   -1.6144 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0874   -0.6077   -2.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469   -0.7566   -2.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    0.2060   -1.7641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2233    0.1179   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305    0.1986    0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3688    0.5523    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820    0.9638    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -0.0035   -0.7045 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1460   -1.4449   -0.2763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -0.0789    0.5943 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0821   -1.5671    0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479    0.1943    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3799   -0.0519    2.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3984    0.5231    1.5302 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1390   -0.4799    0.8625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360    1.4260    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468    0.7043   -0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5730    0.7287   -1.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3986   -0.0544   -2.1126 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398    1.0900    3.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6097    1.6483    2.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9831    2.3340    2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8909    0.5397    0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7754   -1.7104    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6563   -1.4108    2.6339 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4327   -0.9623    2.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441    1.3404    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1837    0.1423    2.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8142   -1.7005    0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943   -0.7018   -0.6466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.7644   -1.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790   -1.1160    0.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511    1.1902   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138   -0.0234   -2.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711    1.5354   -2.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969    1.3829   -1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217    1.3463   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4089   -0.1369   -3.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5778   -1.5768   -2.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495   -1.7939   -2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -0.4268   -3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    1.2397   -2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475   -0.3539    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    1.3942    1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211    0.9407    1.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    1.9718   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486   -1.5706    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8447   -2.0500   -0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.8753   -0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -2.0629   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2669   -2.1095    1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -1.7137   -0.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3373   -0.5790    2.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294    1.1968    2.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5544   -1.1574    2.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5062    0.3271    3.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1544    1.0693    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6197   -0.0291    0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6768    1.6827   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4591    2.3392    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2519    1.2887   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2335    0.3644   -3.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7221   -1.0918   -2.2252 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 14 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
 17  9  1  0
 26 19  1  0
 17 12  1  0
 28 13  1  0
  9 46  1  6
 10 47  1  0
 10 48  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 15 52  1  0
 15 53  1  0
 16 54  1  0
 16 55  1  0
 18 56  1  0
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  0
 22 65  1  0
 23 66  1  1
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 28 71  1  0
 28 72  1  0
  7 42  1  1
  8 43  1  0
  8 44  1  0
  8 45  1  0
  6 40  1  0
  6 41  1  0
  5 38  1  0
  5 39  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


  Mrv0541 02231219192D          

 30 33  0  0  1  0            999 V2000
   14.6941  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6941  -12.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.4085  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1230  -11.2557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4085  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -12.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -12.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -11.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2664  -10.8431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2664  -10.0181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.5519   -9.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -10.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511  -11.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5361  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0511   -9.7632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9795  -12.4932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527   -9.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3061   -8.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1230  -10.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3527  -11.6636    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7540   -8.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1130   -8.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3679   -8.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1750   -7.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4299   -7.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2369   -6.8947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8778   -6.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8275   -9.6250    0.0000 H   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  1  1  0  0  0
 12 19  1  1  0  0  0
 17 20  1  1  0  0  0
  5 21  1  1  0  0  0
 11 22  1  6  0  0  0
 20 23  1  6  0  0  0
 24 20  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 27  1  0  0  0  0
 17 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O/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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
VUKORTMHZDZZFR-BXAZICILSA-N

> <FORMULA>
C27H44O

> <MOLECULAR_WEIGHT>
384.6377

> <EXACT_MASS>
384.33921603

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
50.1424205903791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

> <ALOGPS_LOGP>
6.91

> <JCHEM_LOGP>
6.663651724666668

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.27040487190894

> <JCHEM_PKA_STRONGEST_BASIC>
-1.368324909027029

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
121.19989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-dehydrocholesterol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      27.429 -21.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.429 -22.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.763 -23.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.096 -22.551   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.096 -21.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.763 -20.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.430 -23.321   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.764 -22.551   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.764 -21.011   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.430 -20.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.097 -20.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.097 -18.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.764 -17.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.430 -18.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      35.562 -20.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.467 -19.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.562 -18.225   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.095 -23.321   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.258 -17.169   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.038 -16.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.096 -19.470   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      34.258 -21.772   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      35.007 -15.615   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.544 -16.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      38.020 -14.975   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.527 -14.655   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      40.002 -13.190   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.509 -12.870   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.972 -12.046   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      37.011 -17.967   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5   14                                                  
CONECT   11    9   12   15   22                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20   30                                             
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17   23   24                                                  
CONECT   21    5                                                            
CONECT   22   11                                                            
CONECT   23   20                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   17                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
3b-Cholesta-5,8-dien-3-ol	HMDB
Cholesta-5,8-dien-3 beta-ol	HMDB

Chemical Formula

C₂₇H₄₄O

Average Mass

384.6377 Da

Monoisotopic Mass

384.33922 Da

IUPAC Name

(2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),7-dien-5-ol

Traditional Name

8-dehydrocholesterol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C27H44O/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/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

InChI Key

VUKORTMHZDZZFR-BXAZICILSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
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 (LMST01010242 )

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	6.91	ALOGPS
logP	6.66	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.27	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	5	ChemAxon
Refractivity	121.2 m³·mol⁻¹	ChemAxon
Polarizability	50.14 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

HMDB0002027

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022805

KNApSAcK ID

Not Available

Chemspider ID

114943

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129846

PDB ID

Not Available

ChEBI ID

89982

Good Scents ID

Not Available

References

General References

van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. [PubMed:9266395 ]
Haas D, Armbrust S, Haas JP, Zschocke J, Muhlmann K, Fusch C, Neumann LM: Smith-Lemli-Opitz syndrome with a classical phenotype, oesophageal achalasia and borderline plasma sterol concentrations. J Inherit Metab Dis. 2005;28(6):1191-6. doi: 10.1007/s10545-005-0168-9. [PubMed:16435228 ]
Sikora DM, Pettit-Kekel K, Penfield J, Merkens LS, Steiner RD: The near universal presence of autism spectrum disorders in children with Smith-Lemli-Opitz syndrome. Am J Med Genet A. 2006 Jul 15;140(14):1511-8. doi: 10.1002/ajmg.a.31294. [PubMed:16761297 ]
Chevy F, Humbert L, Wolf C: Sterol profiling of amniotic fluid: a routine method for the detection of distal cholesterol synthesis deficit. Prenat Diagn. 2005 Nov;25(11):1000-6. doi: 10.1002/pd.1254. [PubMed:16231320 ]

Showing NP-Card for 8-Dehydrocholesterol (NP0086845)

MOL for NP0086845 (8-Dehydrocholesterol)

3D MOL for NP0086845 (8-Dehydrocholesterol)

3D SDF for NP0086845 (8-Dehydrocholesterol)

3D-SDF for NP0086845 (8-Dehydrocholesterol)

PDB for NP0086845 (8-Dehydrocholesterol)

3D PDB for NP0086845 (8-Dehydrocholesterol)

SMILES for NP0086845 (8-Dehydrocholesterol)

INCHI for NP0086845 (8-Dehydrocholesterol)

Structure for NP0086845 (8-Dehydrocholesterol)

3D Structure for NP0086845 (8-Dehydrocholesterol)