NP-MRD: Showing NP-Card for lichesterol (NP0231759)

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Record Information

Version

2.0

Created at

2022-09-06 12:45:24 UTC

Updated at

2022-09-06 12:45:24 UTC

NP-MRD ID

NP0231759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lichesterol

Description

Lichesterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, lichesterol is considered to be a sterol. lichesterol is found in Botrytis cinerea and Conium maculatum. lichesterol was first documented in 1994 (PMID: 7985380). Based on a literature review very few articles have been published on Lichesterol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309062214452D          

 29 32  0  0  1  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    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
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -7.1902   -0.1570    0.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9999   -0.2257   -0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2102    0.3244   -1.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287    0.4852   -1.2866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7226    1.9256   -0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5187   -0.2318   -0.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853    0.4052   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274   -0.2710    0.3335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4461   -1.7470   -0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1095    0.3603   -0.2394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0277    1.8188    0.1426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2457    1.8822    0.9593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839    0.9897    0.1059 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3936    0.6405    0.5877 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997   -0.3824   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2728   -1.0264   -1.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913   -1.1476   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2041   -0.2722    0.1355 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2390   -0.9483    1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3462   -0.7699    0.4677 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1755   -1.6743    1.6656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1852   -1.4587   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9508   -0.4141   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1202    0.0128   -0.5125 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9324   -1.0853   -0.2004 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5870    0.5563    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1119    0.4299    0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4922    1.4698    1.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0173    1.4122    1.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3640    0.8701    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2799   -0.5397    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0334   -0.7885    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9115   -1.2985   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5134   -0.3197   -2.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0994    1.3418   -2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0972    0.3311   -0.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6916    0.4759   -2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8337    2.4598   -1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6069    2.4629   -1.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    1.9570    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117   -1.2733   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6926    1.4651    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -0.2250    1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -2.1934    0.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642   -1.9043   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818   -2.2632    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2183    0.2730   -1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8275    2.4003   -0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9018    2.1902    0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    2.9114    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.4405    1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0735    1.3721   -0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -0.3880   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6487   -2.0262   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205   -2.2266   -0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2734   -0.9373   -1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -0.8634    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691   -0.4613    2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6058   -1.9858    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8999   -1.4099    2.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -2.7287    1.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -1.6036    2.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6720   -2.1393   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9626   -2.0498   -0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3299    0.4776   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3355   -0.8930   -2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7757    0.7433   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1309   -1.1416    0.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8795    1.6402    0.7994 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0893    0.1206    1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0499    2.3465    1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814    1.0181    2.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6537    2.4620    1.6779 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 15 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 18 10  1  0
 27 20  1  0
 18 13  1  0
 29 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  6
  5 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  1
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  6
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  6
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 19 57  1  0
 19 58  1  0
 19 59  1  0
 21 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 26 69  1  0
 26 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
M  END

  Mrv1652309062214452D          

 29 32  0  0  1  0            999 V2000
    8.7583   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6302   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    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
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
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 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231759

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22,24-25,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

> <INCHI_KEY>
VILFZDAFELACSG-CMNOFMQQSA-N

> <FORMULA>
C28H44O

> <MOLECULAR_WEIGHT>
396.659

> <EXACT_MASS>
396.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.03399035132985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-5-ol

> <JCHEM_LOGP>
6.588749164333333

> <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>
126.8651

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.458  -0.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   10   19                                             
CONECT   19   18                                                            
CONECT   20   15   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   14                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3beta,22E)-Ergosta-5,8,22-trien-3-ol	Kegg
(3b,22E)-Ergosta-5,8,22-trien-3-ol	Generator
(3Β,22E)-ergosta-5,8,22-trien-3-ol	Generator

Chemical Formula

C₂₈H₄₄O

Average Mass

396.6590 Da

Monoisotopic Mass

396.33922 Da

IUPAC Name

(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-5-ol

Traditional Name

(2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),7-dien-5-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22,24-25,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

InChI Key

VILFZDAFELACSG-CMNOFMQQSA-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
Botrytis cinerea	LOTUS Database	35616633
Conium maculatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-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

ergostanoid (CHEBI:6453 )
Ergosterols and C24-methyl derivatives (LMST01031026 )

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	6.59	ChemAxon
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	4	ChemAxon
Refractivity	126.87 m³·mol⁻¹	ChemAxon
Polarizability	51.03 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

C00003658

Chemspider ID

4444706

KEGG Compound ID

C08823

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lichesterol

METLIN ID

Not Available

PubChem Compound

5281329

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uchida Y, Onodera S, Nakade T, Otomo K: Sterol composition in polyene antibiotic-sensitive and resistant strains of Malassezia pachydermatis. Vet Res Commun. 1994;18(3):183-7. doi: 10.1007/BF01839267. [PubMed:7985380 ]
LOTUS database [Link]

Showing NP-Card for lichesterol (NP0231759)

MOL for NP0231759 (lichesterol)

3D MOL for NP0231759 (lichesterol)

3D SDF for NP0231759 (lichesterol)

3D-SDF for NP0231759 (lichesterol)

PDB for NP0231759 (lichesterol)

3D PDB for NP0231759 (lichesterol)

SMILES for NP0231759 (lichesterol)

INCHI for NP0231759 (lichesterol)

Structure for NP0231759 (lichesterol)

3D Structure for NP0231759 (lichesterol)