NP-MRD: Showing NP-Card for CE(20:4(5Z,8Z,11Z,14Z) (NP0334210)

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Record Information

Version

2.0

Created at

2024-09-09 22:39:10 UTC

Updated at

2024-09-09 22:39:10 UTC

NP-MRD ID

NP0334210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CE(20:4(5Z,8Z,11Z,14Z)

Description

CE(20:4(5Z,8Z,11Z,14Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:Cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. [HMDB]

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252301112D          

 55 58  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0882   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3853   -3.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2615   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0431   -3.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7714   -3.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0263   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9644   -3.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5670   -5.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7465   -5.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8333   -2.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7095   -4.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9025   -4.6770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5749   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2894   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5165   -4.3340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4217   -5.3182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9075   -5.0224    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 37  1  0  0  0  0
  3 37  1  0  0  0  0
 38  4  1  0  0  0  0
 46  5  1  6  0  0  0
 47  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 37  1  0  0  0  0
 38 26  1  0  0  0  0
 27 45  1  0  0  0  0
 28 29  1  0  0  0  0
 28 39  2  0  0  0  0
 41 29  1  0  0  0  0
 30 31  1  0  0  0  0
 42 30  1  0  0  0  0
 43 31  1  0  0  0  0
 32 34  1  0  0  0  0
 40 32  1  0  0  0  0
 33 35  1  0  0  0  0
 44 33  1  0  0  0  0
 46 34  1  0  0  0  0
 47 35  1  0  0  0  0
 36 39  1  0  0  0  0
 40 36  1  0  0  0  0
 38 50  1  6  0  0  0
 42 38  1  1  0  0  0
 46 39  1  0  0  0  0
 40 51  1  6  0  0  0
 40 49  1  0  0  0  0
 41 52  1  1  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 42 53  1  6  0  0  0
 47 42  1  0  0  0  0
 43 54  1  6  0  0  0
 43 47  1  0  0  0  0
 44 55  1  6  0  0  0
 44 46  1  0  0  0  0
 45 48  2  0  0  0  0
 45 49  1  0  0  0  0
M  END


  Mrv2104 05252301112D          

 55 58  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0882   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3853   -3.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2615   -5.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0431   -3.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7714   -3.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0263   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9644   -3.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5670   -5.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7465   -5.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8333   -2.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7095   -4.5055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9025   -4.6770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5749   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2894   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5165   -4.3340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4217   -5.3182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9075   -5.0224    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 37  1  0  0  0  0
  3 37  1  0  0  0  0
 38  4  1  0  0  0  0
 46  5  1  6  0  0  0
 47  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 27  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 37  1  0  0  0  0
 38 26  1  0  0  0  0
 27 45  1  0  0  0  0
 28 29  1  0  0  0  0
 28 39  2  0  0  0  0
 41 29  1  0  0  0  0
 30 31  1  0  0  0  0
 42 30  1  0  0  0  0
 43 31  1  0  0  0  0
 32 34  1  0  0  0  0
 40 32  1  0  0  0  0
 33 35  1  0  0  0  0
 44 33  1  0  0  0  0
 46 34  1  0  0  0  0
 47 35  1  0  0  0  0
 36 39  1  0  0  0  0
 40 36  1  0  0  0  0
 38 50  1  6  0  0  0
 42 38  1  1  0  0  0
 46 39  1  0  0  0  0
 40 51  1  6  0  0  0
 40 49  1  0  0  0  0
 41 52  1  1  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 42 53  1  6  0  0  0
 47 42  1  0  0  0  0
 43 54  1  6  0  0  0
 43 47  1  0  0  0  0
 44 55  1  6  0  0  0
 44 46  1  0  0  0  0
 45 48  2  0  0  0  0
 45 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@@]4(C)[C@@]3([H])CC[C@@]12C)OC(=O)CCC\C=C\C\C=C\C\C=C\C\C=C\CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C47H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11+,15-14+,18-17+,21-20+/t38-,40+,41+,42-,43+,44+,46-,47+/m1/s1

> <INCHI_KEY>
IMXSFYNMSOULQS-VZGLVKIESA-N

> <FORMULA>
C47H76O2

> <MOLECULAR_WEIGHT>
673.123

> <EXACT_MASS>
672.584531687

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
85.37739533963362

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3aS,3bS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate

> <JCHEM_LOGP>
14.364530966333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0423161829669185

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
217.07830000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
20:4 cholesterol ester

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.765  -3.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.319  -5.985   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.355  -9.555   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.006  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.080  -7.074   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.307  -6.625   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.782  -5.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.800  -6.946   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.673  -8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.192 -10.137   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.660  -9.976   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      22.673  -3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      26.674  -6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      33.289  -4.841   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      29.324  -8.410   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      21.339  -6.160   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.006  -7.700   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      27.818  -8.730   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      25.340  -8.470   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      24.006  -6.160   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.674  -7.700   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      18.672  -3.080   0.000  0.00  0.00           O+0
HETATM   50  H   UNK     0      30.831  -8.090   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      20.005  -2.310   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0      25.340  -6.930   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0      28.787  -9.927   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      24.094  -9.375   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      22.673  -6.930   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   37                                                            
CONECT    3   37                                                            
CONECT    4   38                                                            
CONECT    5   46                                                            
CONECT    6   47                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   27                                                       
CONECT   24   25   26                                                       
CONECT   25   24   37                                                       
CONECT   26   24   38                                                       
CONECT   27   23   45                                                       
CONECT   28   29   39                                                       
CONECT   29   28   41                                                       
CONECT   30   31   42                                                       
CONECT   31   30   43                                                       
CONECT   32   34   40                                                       
CONECT   33   35   44                                                       
CONECT   34   32   46                                                       
CONECT   35   33   47                                                       
CONECT   36   39   40                                                       
CONECT   37    2    3   25                                                  
CONECT   38    4   26   50   42                                             
CONECT   39   28   36   46                                                  
CONECT   40   32   36   51   49                                             
CONECT   41   29   52   43   44                                             
CONECT   42   30   38   53   47                                             
CONECT   43   31   41   54   47                                             
CONECT   44   33   41   55   46                                             
CONECT   45   27   48   49                                                  
CONECT   46    5   34   39   44                                             
CONECT   47    6   35   42   43                                             
CONECT   48   45                                                            
CONECT   49   40   45                                                       
CONECT   50   38                                                            
CONECT   51   40                                                            
CONECT   52   41                                                            
CONECT   53   42                                                            
CONECT   54   43                                                            
CONECT   55   44                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₆O₂

Average Mass

673.1230 Da

Monoisotopic Mass

672.58453 Da

IUPAC Name

(1R,3aS,3bS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate

Traditional Name

20:4 cholesterol ester

CAS Registry Number

Not Available

SMILES

[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@@]4(C)[C@@]3([H])CC[C@@]12C)OC(=O)CCC\C=C\C\C=C\C\C=C\C\C=C\CCCCC

InChI Identifier

InChI=1S/C47H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11+,15-14+,18-17+,21-20+/t38-,40+,41+,42-,43+,44+,46-,47+/m1/s1

InChI Key

IMXSFYNMSOULQS-VZGLVKIESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Cholesteryl esters

Alternative Parents

Substituents

Cholesteryl ester
Cholesterol
Cholestane-skeleton
Delta-5-steroid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	14.36	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	217.08 m³·mol⁻¹	ChemAxon
Polarizability	85.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for CE(20:4(5Z,8Z,11Z,14Z) (NP0334210)

MOL for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

3D MOL for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

3D SDF for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

3D-SDF for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

PDB for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

3D PDB for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

SMILES for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

INCHI for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

Structure for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))

3D Structure for NP0334210 (CE(20:4(5Z,8Z,11Z,14Z))