NP-MRD: Showing NP-Card for 4alpha-Methyl-5alpha-cholesta-8-en-3-one (NP0091963)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 18:53:17 UTC

Updated at

2022-05-11 18:53:17 UTC

NP-MRD ID

NP0091963

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4alpha-Methyl-5alpha-cholesta-8-en-3-one

Description

4Alpha-methyl-5alpha-cholesta-8-en-3-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 4Alpha-methyl-5alpha-cholesta-8-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It can be generated from the enzymatic reduction of 4A-methyl-cholesta-8-enol or enzymatic oxidation of 4a-carboxy-4b-methyl-5a-cholesta-8-en-3b-ol. Alternate routes exist because reduction of the carbon 24,25 double bond on the hydrocarbon side chain of the sterol ring structure by sterol delta24-reductase can occur at multiple points in the pathway, giving rise to different intermediates.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203482D          

 29 32  0  0  1  0            999 V2000
   16.6729  -10.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6109  -11.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5959   -9.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2528  -10.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -11.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -10.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -10.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9549   -9.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -11.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -12.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -13.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -10.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8659  -10.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479  -10.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -10.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505  -14.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.1535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9650  -12.3910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2505  -13.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8216  -13.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 11  1  0  0  0  0
 11 21  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 24  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 26  1  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  2  0  0  0  0
 24 28  1  0  0  0  0
 28 25  1  6  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
   -7.8362    1.4844    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8423    0.9152   -0.6169 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1522   -0.5640   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4235    1.1203   -0.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4722    0.5603   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0302    0.6890   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7289   -0.0309    0.5513 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0457   -1.4827    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945    0.3137    1.1186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1915   -0.4606    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1458   -1.1786    2.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520   -0.1174    1.3922 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1117   -0.4413    0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813    0.3037   -0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7093    1.4900   -0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250    1.5653   -0.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906    0.2142    0.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1190   -0.7580   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7086    0.0072   -1.0563 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2250   -0.3791   -2.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5164    1.2782   -1.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8900    0.9537   -1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6231    0.2470   -0.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8437    0.3399   -0.5785 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8129   -0.5921    0.2068 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5611    0.0341    1.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739   -1.0625   -0.5246 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8389   -2.1279    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055   -1.5770    1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9318    2.5740    0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6125    1.1519    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8350    1.0559    0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0177    1.4170   -1.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1172   -0.8338   -0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1542   -0.9352   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3717   -1.1102   -0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2759    2.2118    0.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4101    0.6718    0.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6711    1.1058   -2.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7409   -0.5114   -1.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8474    1.7820   -0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    0.3912   -1.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4643    0.4049    1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029   -1.7157    1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047   -1.8103   -0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -2.1163    0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    1.3981    1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939   -1.1331    2.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9861    0.1935    3.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6346   -1.3652    3.1249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012   -2.1130    1.6035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9767    0.7637    2.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2927    2.3837   -0.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549    1.4840   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3105    2.2979    0.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3555    1.9556   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -1.4460   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709   -1.4423   -0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1616   -0.2508   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0476   -0.9470   -2.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0045    0.5318   -3.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399   -1.0329   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    1.9125   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0061    1.8755   -2.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3820    1.9129   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7659    0.2848   -2.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4216   -1.5310    0.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6901   -0.7315    2.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6507    0.6169    1.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125    0.7535    1.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9969   -1.6213   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -2.7256    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2934   -2.7637   -0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553   -2.3901    1.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3756   -1.3484    2.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  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  6
 14 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 17  9  1  0
 27 19  1  0
 17 12  1  0
 29 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  6 42  1  0
  7 43  1  1
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  1
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 20 60  1  0
 20 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 25 67  1  1
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
M  END


  Mrv0541 02241203482D          

 29 32  0  0  1  0            999 V2000
   16.6729  -10.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6109  -11.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5959   -9.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2528  -10.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -11.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5069  -10.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -10.3840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9549   -9.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3779  -11.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -12.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -13.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -10.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8659  -10.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479  -10.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3939  -12.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8930  -10.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6794  -11.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9650  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5360  -13.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2505  -14.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1083  -11.1535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9650  -12.3910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2505  -13.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8216  -13.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 17  1  0  0  0  0
  3 18  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 12  1  0  0  0  0
 10 20  1  0  0  0  0
 10 11  1  0  0  0  0
 11 21  1  0  0  0  0
 12 23  1  0  0  0  0
 13 22  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 24  1  0  0  0  0
 15 26  1  0  0  0  0
 16 27  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 26  1  0  0  0  0
 21 26  1  0  0  0  0
 22 27  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  1  0  0  0  0
 24 29  2  0  0  0  0
 24 28  1  0  0  0  0
 28 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0091963

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24H,7-17H2,1-6H3/t19?,20-,22?,23?,24?,27+,28-/m0/s1

> <INCHI_KEY>
SDZUXFFGOQZLPK-RJBGAFQBSA-N

> <FORMULA>
C28H46O

> <MOLECULAR_WEIGHT>
398.6642

> <EXACT_MASS>
398.354866094

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
51.3825266453277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6S,15R)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
7.8197182860000005

> <ALOGPS_LOGS>
-6.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.826726067146463

> <JCHEM_PKA_STRONGEST_BASIC>
-7.412274411747466

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
123.89629999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6S,15R)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      31.123 -20.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.140 -21.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.512 -17.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.872 -19.304   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.601 -21.590   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.080 -19.704   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.586 -19.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.049 -18.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.269 -24.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.972 -21.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.067 -22.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.935 -25.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.935 -20.820   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.934 -23.130   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.269 -20.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.268 -22.360   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.616 -20.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.543 -18.879   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.269 -23.130   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.067 -20.344   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.602 -22.360   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.935 -22.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.601 -24.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.934 -24.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.268 -26.980   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      22.602 -20.820   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.601 -23.130   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.268 -25.440   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.600 -25.440   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7    8                                                       
CONECT    7    6   17                                                       
CONECT    8    6   18                                                       
CONECT    9   19   12                                                       
CONECT   10   20   11                                                       
CONECT   11   10   21                                                       
CONECT   12    9   23                                                       
CONECT   13   22   15                                                       
CONECT   14   16   24                                                       
CONECT   15   13   26                                                       
CONECT   16   14   27                                                       
CONECT   17    1    2    7                                                  
CONECT   18    3    8   20                                                  
CONECT   19    9   21   22                                                  
CONECT   20   10   18   26                                                  
CONECT   21   11   19   26                                                  
CONECT   22   13   19   27                                                  
CONECT   23   12   27   28                                                  
CONECT   24   14   29   28                                                  
CONECT   25   28                                                            
CONECT   26    4   15   20   21                                             
CONECT   27    5   16   22   23                                             
CONECT   28   23   24   25                                                  
CONECT   29   24                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
4a-Methyl-5a-cholesta-8-en-3-one	Generator
4Α-methyl-5α-cholesta-8-en-3-one	Generator

Chemical Formula

C₂₈H₄₆O

Average Mass

398.6642 Da

Monoisotopic Mass

398.35487 Da

IUPAC Name

(2S,6S,15R)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

Traditional Name

(2S,6S,15R)-2,6,15-trimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one

CAS Registry Number

Not Available

SMILES

CC(C)CCCC(C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)[C@@H](C)C1CC3

InChI Identifier

InChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h18-20,22-24H,7-17H2,1-6H3/t19?,20-,22?,23?,24?,27+,28-/m0/s1

InChI Key

SDZUXFFGOQZLPK-RJBGAFQBSA-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
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.22	ALOGPS
logP	7.82	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.9 m³·mol⁻¹	ChemAxon
Polarizability	51.38 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

HMDB0012174

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028828

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

25202835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4alpha-Methyl-5alpha-cholesta-8-en-3-one (NP0091963)

MOL for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

3D MOL for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

3D SDF for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

3D-SDF for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

PDB for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

3D PDB for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

SMILES for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

INCHI for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

Structure for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)

3D Structure for NP0091963 (4alpha-Methyl-5alpha-cholesta-8-en-3-one)