MiMeDB: Showing metabocard for CE(18:1(9Z)) (MMDBc0048100)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:50:44 UTC

Update Date

2024-04-30 20:35:38 UTC

Metabolite ID

MMDBc0048100

Metabolite Identification

Common Name

CE(18:1(9Z))

Description

CE(18:1(9Z)), also known as cholesteryl oleate, is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Cholesteryl esters, formed by the esterification of cholesterol with long-chain fatty acids, on one hand, are the means by which cholesterol is transported through the blood by lipoproteins, on the other, the way cholesterol itself can be accumulated in the cells. (PMID: 15939411 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310061800272D          

 55 58  0  0  1  0            999 V2000
  -12.8605    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3993   -3.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403   -3.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    2.4750    0.0000 C   0  0  0  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
   -8.5737    2.4750    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
   -7.1447    2.4750    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
   -5.7158    2.4750    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
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    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
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  2  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
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -1.8242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0284   -0.3840    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 21  1  0  0  0  0
 27 26  1  0  0  0  0
 29 28  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 35  2  1  0  0  0  0
 35  3  1  0  0  0  0
 35 23  1  0  0  0  0
 36  4  1  1  0  0  0
 36 24  1  0  0  0  0
 37 26  2  0  0  0  0
 37 34  1  0  0  0  0
 38 30  1  0  0  0  0
 38 34  1  0  0  0  0
 39 27  1  0  0  0  0
 40 28  1  0  0  0  0
 40 36  1  6  0  0  0
 41 29  1  0  0  0  0
 41 39  1  0  0  0  0
 42 31  1  0  0  0  0
 42 39  1  0  0  0  0
 43 25  1  0  0  0  0
 44  5  1  6  0  0  0
 44 32  1  0  0  0  0
 44 37  1  0  0  0  0
 44 42  1  0  0  0  0
 45  6  1  6  0  0  0
 45 33  1  0  0  0  0
 45 40  1  0  0  0  0
 45 41  1  0  0  0  0
 46 43  2  0  0  0  0
 38 47  1  6  0  0  0
 47 43  1  0  0  0  0
 48 14  1  0  0  0  0
 49 15  1  0  0  0  0
 36 50  1  6  0  0  0
 38 51  1  1  0  0  0
 39 52  1  6  0  0  0
 40 53  1  1  0  0  0
 41 54  1  1  0  0  0
 42 55  1  1  0  0  0
M  END


  Mrv1652310061800272D          

 55 58  0  0  1  0            999 V2000
  -12.8605    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3993   -3.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0403   -3.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9165   -1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    2.4750    0.0000 C   0  0  0  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
   -8.5737    2.4750    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
   -7.1447    2.4750    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
   -5.7158    2.4750    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
    3.5304   -1.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    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
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.0396    0.0000 C   0  0  2  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
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234   -1.8242    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0284   -0.3840    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  1  0  0  0  0
 25 21  1  0  0  0  0
 27 26  1  0  0  0  0
 29 28  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
 35  2  1  0  0  0  0
 35  3  1  0  0  0  0
 35 23  1  0  0  0  0
 36  4  1  1  0  0  0
 36 24  1  0  0  0  0
 37 26  2  0  0  0  0
 37 34  1  0  0  0  0
 38 30  1  0  0  0  0
 38 34  1  0  0  0  0
 39 27  1  0  0  0  0
 40 28  1  0  0  0  0
 40 36  1  6  0  0  0
 41 29  1  0  0  0  0
 41 39  1  0  0  0  0
 42 31  1  0  0  0  0
 42 39  1  0  0  0  0
 43 25  1  0  0  0  0
 44  5  1  6  0  0  0
 44 32  1  0  0  0  0
 44 37  1  0  0  0  0
 44 42  1  0  0  0  0
 45  6  1  6  0  0  0
 45 33  1  0  0  0  0
 45 40  1  0  0  0  0
 45 41  1  0  0  0  0
 46 43  2  0  0  0  0
 38 47  1  6  0  0  0
 47 43  1  0  0  0  0
 48 14  1  0  0  0  0
 49 15  1  0  0  0  0
 36 50  1  6  0  0  0
 38 51  1  1  0  0  0
 39 52  1  6  0  0  0
 40 53  1  1  0  0  0
 41 54  1  1  0  0  0
 42 55  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048100

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C45H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

> <INCHI_KEY>
RJECHNNFRHZQKU-RMUVNZEASA-N

> <FORMULA>
C45H78O2

> <MOLECULAR_WEIGHT>
651.0996

> <EXACT_MASS>
650.60018174

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
86.81092553558278

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate

> <ALOGPS_LOGP>
10.68

> <JCHEM_LOGP>
14.561158606333336

> <ALOGPS_LOGS>
-8.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042198548687182

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
204.52650000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.33e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-OCT-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-OCT-18         0                                  
HETATM    1  C   UNK     0     -24.006  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.079  -5.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.542  -6.655   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.577  -3.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.828  -1.532   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -22.673  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -22.673  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -21.339  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -21.339   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -20.005   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -20.005   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -18.672   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -18.672   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -17.338   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.096  -4.046   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.114  -2.261   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.608  -1.941   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   48  H   UNK     0     -20.005   3.850   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0     -17.338   2.310   0.000  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.084  -3.405   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.001   5.390   0.000  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.653  -0.717   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.000   3.080   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   35                                                            
CONECT    3   35                                                            
CONECT    4   36                                                            
CONECT    5   44                                                            
CONECT    6   45                                                            
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   48                                                  
CONECT   15   14   16   49                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   25                                                       
CONECT   22   23   24                                                       
CONECT   23   22   35                                                       
CONECT   24   22   36                                                       
CONECT   25   21   43                                                       
CONECT   26   27   37                                                       
CONECT   27   26   39                                                       
CONECT   28   29   40                                                       
CONECT   29   28   41                                                       
CONECT   30   32   38                                                       
CONECT   31   33   42                                                       
CONECT   32   30   44                                                       
CONECT   33   31   45                                                       
CONECT   34   37   38                                                       
CONECT   35    2    3   23                                                  
CONECT   36    4   24   40   50                                             
CONECT   37   26   34   44                                                  
CONECT   38   30   34   47   51                                             
CONECT   39   27   41   42   52                                             
CONECT   40   28   36   45   53                                             
CONECT   41   29   39   45   54                                             
CONECT   42   31   39   44   55                                             
CONECT   43   25   46   47                                                  
CONECT   44    5   32   37   42                                             
CONECT   45    6   33   40   41                                             
CONECT   46   43                                                            
CONECT   47   38   43                                                       
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   36                                                            
CONECT   51   38                                                            
CONECT   52   39                                                            
CONECT   53   40                                                            
CONECT   54   41                                                            
CONECT   55   42                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

Synonyms

Value	Source
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoate	ChEBI
18:1 Cholesteryl ester	ChEBI
CE(18:1)	ChEBI
Cholest-5-en-3-beta-yl oleate	ChEBI
Cholest-5-en-3-yl (9Z)-9-octadecenoate	ChEBI
Cholesteryl (9Z-octadecenoate)	ChEBI
Cholesteryl cis-9-octadecenoate	ChEBI
Oleoylcholesterol	ChEBI
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoate	Generator
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acid	Generator
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acid	Generator
(3Β)-cholest-5-en-3-ol, (Z)-9-octadecenoate	Generator
(3Β)-cholest-5-en-3-ol, (Z)-9-octadecenoic acid	Generator
Cholest-5-en-3-b-yl oleate	Generator
Cholest-5-en-3-b-yl oleic acid	Generator
Cholest-5-en-3-beta-yl oleic acid	Generator
Cholest-5-en-3-β-yl oleate	Generator
Cholest-5-en-3-β-yl oleic acid	Generator
Cholest-5-en-3-yl (9Z)-9-octadecenoic acid	Generator
Cholesteryl (9Z-octadecenoic acid)	Generator
Cholesteryl cis-9-octadecenoic acid	Generator
1-Oleoyl-cholesterol	HMDB
18:1(9Z) Cholesterol ester	HMDB
3beta-Hydroxy-5-cholestene 3-oleate	HMDB
5-Cholesten-3b-ol 3-oleate	HMDB
CE(18:1/0:0)	HMDB
CE(18:1n9/0:0)	HMDB
CE(18:1W9/0:0)	HMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoate	HMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acid	HMDB
Cholest-5-en-3b-yl	HMDB
Cholesterol 1-(9Z-octadecenoate	HMDB
Cholesterol 1-(9Z-octadecenoate)	HMDB
Cholesterol 1-(9Z-octadecenoic acid	HMDB
Cholesterol 1-(9Z-octadecenoic acid)	HMDB
Cholesterol 3beta-oleate	HMDB
Cholesterol ester(18:1)	HMDB
Cholesterol ester(18:1/0:0)	HMDB
Cholesterol ester(18:1n9/0:0)	HMDB
Cholesterol ester(18:1W9/0:0)	HMDB
Cholesteroyl-oleate	HMDB
Cholesteryl 1-oleoate	HMDB
Cholesteryl 1-oleoic acid	HMDB
Cholesteryl oleate	HMDB, MeSH
Cholesteryl oleate-9,10-3H	HMDB
Cholesteryl oleate-9,10-t2	HMDB
Cholesteryl oleic ester	HMDB
Cholesteryl [9,10-3H]oleate	HMDB
Cholesteryl-beta-D-glucoside	HMDB
Cholesteryl-beta-delta-glucoside	HMDB
Oleic acid cholesteryl ester	HMDB
Cholesteryl oleate, (e)-isomer	MeSH
Cholesterol oleate	MeSH
CE(18:1(9Z))	ChEBI
Cholesteryl oleic acid	Generator

Molecular Formula

C₄₅H₇₈O₂

Average Mass

651.0996

Monoisotopic Mass

650.60018174

IUPAC Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate

Traditional Name

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-octadec-9-enoate

CAS Registry Number

303-43-5

SMILES

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@@]1([H])CC[C@@]2(C)C(C1)=CC[C@@]1([H])[C@]3([H])CC[C@]([H])([C@]([H])(C)CCCC(C)C)[C@@]3(C)CC[C@]21[H]

InChI Identifier

InChI=1S/C45H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

InChI Key

RJECHNNFRHZQKU-RMUVNZEASA-N

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

cholesteryl octadec-9-enoate (CHEBI:46898 )
Steryl esters (LMST01020003 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.3e-06 g/L	ALOGPS
logP	10.68	ALOGPS
logP	14.56	ChemAxon
logS	-8	ALOGPS
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	22	ChemAxon
Refractivity	204.53 m³·mol⁻¹	ChemAxon
Polarizability	86.81 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-5359047000-b0786012be7d0cac7c83	2017-09-01	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0000009000-21a92605782172dbfd15	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0000009000-06ae92b73dd60f6a7e36	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002o-0800980000-fc08d63d7e4e8b45f921	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-1165029000-1ce7930cf3150163fd8d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-5379031000-e18668a49f8d8d48ee71	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0629-6369130000-9782f8bcc5e881bea861	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0024009000-dccc63058b1b8d7cddc9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0049003000-755458c70f1eed13712d	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-2029000000-170f3ca0c9bd97272276	2017-09-01	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Blood
Epidermis
Feces
Fibroblasts
Intestine
Liver
Neuron
Platelet
Spleen
Testis

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002874	Cholesterol	CE(18:1(9Z))	sterol O-acyltransferase 1	VMH	2760547 7822296 9242919
MMDBr0002883	CE(18:1(9Z))	Cholesterol	carboxyl ester lipase	VMH	11230747 8112342
MMDBr0002884	CE(18:1(9Z))	Cholesterol	carboxyl ester lipase	VMH	11230747 8112342

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	533	13	uM	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human Blood	Detected and Quantified	704.47	129.59	uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	704.47	129.59	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Adipose tissue	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal cortex	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Spleen	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14641

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283632

PDB ID

Not Available

ChEBI ID

46898

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Albers JJ, Marcovina SM, Christenson RH: Lecithin cholesterol acyltransferase in human cerebrospinal fluid: reduced level in patients with multiple sclerosis and evidence of direct synthesis in the brain. Int J Clin Lab Res. 1992;22(3):169-72. doi: 10.1007/BF02591418. [PubMed:1387817 ]
Gwynne JT, Mahaffee DD: Rat adrenal uptake and metabolism of high density lipoprotein cholesteryl ester. J Biol Chem. 1989 May 15;264(14):8141-50. [PubMed:2542267 ]
Kuipers F, Nagelkerke JF, Bakkeren H, Havinga R, Van Berkel TJ, Vonk RJ: Processing of cholesteryl ester from low-density lipoproteins in the rat. Hepatic metabolism and biliary secretion after uptake by different hepatic cell types. Biochem J. 1989 Feb 1;257(3):699-704. doi: 10.1042/bj2570699. [PubMed:2930479 ]
Tall A, Granot E, Brocia R, Tabas I, Hesler C, Williams K, Denke M: Accelerated transfer of cholesteryl esters in dyslipidemic plasma. Role of cholesteryl ester transfer protein. J Clin Invest. 1987 Apr;79(4):1217-25. doi: 10.1172/JCI112940. [PubMed:3558822 ]
Busch SJ, Stuart WD, Hug B, Mao SJ, Harmony JA: Plasma cholesteryl ester-triglyceride transfer protein. The catalytic domain is a low molecular weight proteolipid. J Biol Chem. 1987 Dec 25;262(36):17563-71. [PubMed:3693366 ]
Sklar LA, Craig IF, Pownall HJ: Induced circular dichroism of incorporated fluorescent cholesteryl esters and polar lipids as a probe of human serum low density lipoprotein structure and melting. J Biol Chem. 1981 May 10;256(9):4286-92. [PubMed:7217083 ]
Matsuda K: ACAT inhibitors as antiatherosclerotic agents: compounds and mechanisms. Med Res Rev. 1994 May;14(3):271-305. doi: 10.1002/med.2610140302. [PubMed:8007738 ]
Oliveira HC, Nilausen K, Meinertz H, Quintao EC: Cholesteryl esters in lymph chylomicrons: contribution from high density lipoprotein transferred from plasma into intestinal lymph. J Lipid Res. 1993 Oct;34(10):1729-36. [PubMed:8245723 ]
Benoist F, Lau P, McDonnell M, Doelle H, Milne R, McPherson R: Cholesteryl ester transfer protein mediates selective uptake of high density lipoprotein cholesteryl esters by human adipose tissue. J Biol Chem. 1997 Sep 19;272(38):23572-7. doi: 10.1074/jbc.272.38.23572. [PubMed:9295295 ]
Katan MB, Deslypere JP, van Birgelen AP, Penders M, Zegwaard M: Kinetics of the incorporation of dietary fatty acids into serum cholesteryl esters, erythrocyte membranes, and adipose tissue: an 18-month controlled study. J Lipid Res. 1997 Oct;38(10):2012-22. [PubMed:9374124 ]
Ceryak S, Bouscarel B, Malavolti M, Robins SJ, Caslow KL, Fromm H: Effect of ursodeoxycholic acid on hepatic LDL binding and uptake in dietary hypercholesterolemic hamsters. Atherosclerosis. 2000 Nov;153(1):59-67. doi: 10.1016/s0021-9150(00)00396-8. [PubMed:11058700 ]
Adam O, Wolfram G, Zollner N: Influence of dietary linoleic acid intake with different fat intakes on arachidonic acid concentrations in plasma and platelet lipids and eicosanoid biosynthesis in female volunteers. Ann Nutr Metab. 2003;47(1):31-6. doi: 10.1159/000068906. [PubMed:12624485 ]
Tosi MR, Tugnoli V: Cholesteryl esters in malignancy. Clin Chim Acta. 2005 Sep;359(1-2):27-45. doi: 10.1016/j.cccn.2005.04.003. [PubMed:15939411 ]
Seo T, Qi K, Chang C, Liu Y, Worgall TS, Ramakrishnan R, Deckelbaum RJ: Saturated fat-rich diet enhances selective uptake of LDL cholesteryl esters in the arterial wall. J Clin Invest. 2005 Aug;115(8):2214-22. doi: 10.1172/JCI24327. Epub 2005 Jul 21. [PubMed:16041409 ]
Hui SP, Murai T, Yoshimura T, Chiba H, Nagasaka H, Kurosawa T: Improved HPLC assay for lipid peroxides in human plasma using the internal standard of hydroperoxide. Lipids. 2005 May;40(5):515-22. doi: 10.1007/s11745-005-1412-2. [PubMed:16094862 ]

Showing metabocard for CE(18:1(9Z)) (MMDBc0048100)

MOL for #<Metabolite:0x00007fecd802c6d8>

3D MOL for #<Metabolite:0x00007fecd802c6d8>

3D SDF for #<Metabolite:0x00007fecd802c6d8>

3D-SDF for #<Metabolite:0x00007fecd802c6d8>

PDB for #<Metabolite:0x00007fecd802c6d8>

3D PDB for #<Metabolite:0x00007fecd802c6d8>

SMILES for #<Metabolite:0x00007fecd802c6d8>

INCHI for #<Metabolite:0x00007fecd802c6d8>

Structure for #<Metabolite:0x00007fecd802c6d8>

3D Structure for #<Metabolite:0x00007fecd802c6d8>