NP-MRD: Showing NP-Card for (7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate (NP0299018)

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Record Information

Version

1.0

Created at

2022-09-10 10:36:47 UTC

Updated at

2022-09-10 10:36:47 UTC

NP-MRD ID

NP0299018

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate

Description

CE(22:2(13Z,16Z)), also known as ce(22:2/0:0), Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. A cholesteryl ester is an ester of cholesterol. CE(22:2(13Z,16Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). Ce(22:2(13Z,16Z)) can be converted into cholesterol and palmitic acid through its interaction with the enzyme lysosomal acid lipase/cholesteryl ester hydrolase. In humans, ce(22:2(13Z,16Z)) is involved in the metabolic disorder called familial hypercholanemia (fhca). 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. Atherosclerosis is a disease affecting arterial blood vessels. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. 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). 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. (7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate is found in Apis cerana. CE(22:2(13Z,16Z)) is a cholesteryl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220502D          

 51 54  0  0  1  0            999 V2000
   16.4404   -8.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8900   -5.6779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8900   -6.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1755   -6.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4610   -6.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6707   -5.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1755   -5.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7102   -6.9211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.6707   -6.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4610   -5.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1522   -6.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1888   -7.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9270   -4.6423    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8900   -4.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7035   -7.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9455   -6.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4478   -8.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7166   -6.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9318   -8.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1634   -6.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7344   -4.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1566   -7.7865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3761   -4.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9907   -3.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7979   -3.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0542   -2.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5033   -2.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8616   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7224   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1513   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8658   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4381   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1525   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8669   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5815   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2959   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0104   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7248   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4392   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1536   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8681   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5827   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2971   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0115   -8.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7259   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7259   -6.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 14  1  1  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  1  0  0  0  0
  7 10  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 18  1  1  0  0  0
  9 11  1  0  0  0  0
 12 17  1  0  0  0  0
 13 21  1  0  0  0  0
 13 23  1  6  0  0  0
 15 17  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50  1  1  0  0  0  0
 50 51  2  0  0  0  0
M  END

     RDKit          3D

135138  0  0  0  0  0  0  0  0999 V2000
  -16.1761   -3.2500    0.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6521   -3.2101   -0.6328 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5939   -2.0846   -0.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0646   -0.7175   -0.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8411   -0.4536   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3072    0.8894   -1.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0957    1.1393   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -12.7010    0.1339    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4272    0.2863    1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4979    1.6825   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6622    2.9133   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9259    3.2753    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9466    2.2143    0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3105    2.7952    2.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3053    1.8805    2.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1591    1.5424    1.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361    2.7817    1.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2994    2.4619    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2856    1.6269    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    1.3181    2.2844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8137    1.1152    0.3694 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8071   -1.0827    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1447   -1.6978    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0456   -0.8410   -0.5900 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.1121    0.5106    0.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0941    1.3061   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2074   -1.2682    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6101    0.2257   -1.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3176   -0.5253   -0.5052 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6405   -0.9576    0.0400 C   0  0  2  0  0  0  0  0  0  0  0  0
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   12.7688    0.1165    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6298   -0.7204   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1330    0.9893    1.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4906   -4.1422    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3819   -0.9477   -2.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
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 50132  1  0
 50133  1  0
M  END


  Mrv0541 02231220502D          

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   15.7259   -6.9588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
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 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
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 50 51  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C49H84O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h11-12,14-15,30,39-40,42-46H,7-10,13,16-29,31-38H2,1-6H3/b12-11-,15-14-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1

> <INCHI_KEY>
YSGVSTJGBYXXIM-OVUVNFMNSA-N

> <FORMULA>
C49H84O2

> <MOLECULAR_WEIGHT>
705.1901

> <EXACT_MASS>
704.647131932

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
94.6350235701685

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (13Z,16Z)-docosa-13,16-dienoate

> <ALOGPS_LOGP>
10.94

> <JCHEM_LOGP>
15.977511609666667

> <ALOGPS_LOGS>
-8.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0421985486871135

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
224.0471

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (13Z,16Z)-docosa-13,16-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.689 -15.300   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      38.995 -10.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      38.995 -12.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      37.661 -12.909   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      36.327 -12.139   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      40.452 -10.129   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.661  -9.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.926 -12.919   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.452 -12.608   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.327 -10.599   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.351 -11.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.686 -14.513   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.930  -8.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.995  -9.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.913 -14.524   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.498 -12.051   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.303 -15.326   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.938 -11.379   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.473 -15.370   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.038 -12.864   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      42.438  -8.348   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.026 -14.535   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      39.902  -7.519   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.916  -6.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      44.423  -6.567   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      44.901  -5.103   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      43.873  -3.956   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      46.408  -4.785   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.348 -15.300   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.682 -14.530   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.016 -15.300   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.349 -14.530   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.683 -15.300   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.017 -14.530   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.351 -14.530   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.684 -15.300   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.018 -14.530   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.351 -14.530   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.685 -15.300   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.019 -14.530   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.352 -15.300   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.686 -14.530   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      20.020 -15.300   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.353 -14.530   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      22.687 -15.300   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      24.020 -14.530   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      25.354 -15.300   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      26.688 -14.530   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      28.021 -15.300   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      29.355 -14.530   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      29.355 -12.990   0.000  0.00  0.00           O+0
CONECT    1   22   50                                                       
CONECT    2    3    6    7   14                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    8   10                                                  
CONECT    6    2   11   13                                                  
CONECT    7    2   10                                                       
CONECT    8    5   15   16   18                                             
CONECT    9    3   11                                                       
CONECT   10    5    7                                                       
CONECT   11    6    9                                                       
CONECT   12    4   17                                                       
CONECT   13    6   21   23                                                  
CONECT   14    2                                                            
CONECT   15    8   17   19                                                  
CONECT   16    8   20                                                       
CONECT   17   12   15                                                       
CONECT   18    8                                                            
CONECT   19   15   22                                                       
CONECT   20   16   22                                                       
CONECT   21   13   24                                                       
CONECT   22    1   19   20                                                  
CONECT   23   13                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   30                                                            
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49    1   51                                                  
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

View in JSmol

Synonyms

Value	Source
22:2 Cholesterol ester	HMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoate	HMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoate)	HMDB
Cholest-5-en-3beta-yl (13Z,16Z-docosadienoic acid	HMDB
Cholesteryl docosadienoate	HMDB
Cholesteryl docosadienoic acid	HMDB
Cholesteryl 1-(13Z,16Z-docosadienoic acid)	HMDB
Cholesterol 1-docosadienoic acid	HMDB
CE(22:2/0:0)	HMDB
CE(22:2)	HMDB
Cholesterol 1-(13Z,16Z-docosadienoate)	HMDB
Cholesteryl 1-docosadienoic acid	HMDB
Cholesterol 1-docosadienoate	HMDB
1-Docosadienoyl-cholesterol	HMDB
22:2(13Z,16Z) Cholesterol ester	HMDB
Cholesterol ester(22:2)	HMDB
Cholesteryl 1-docosadienoate	HMDB
Cholesteryl 1-(13Z,16Z-docosadienoate)	HMDB
Cholesterol ester(22:2/0:0)	HMDB
1-(13Z,16Z-Docosadienoyl)-cholesterol	HMDB
Cholesterol 1-(13Z,16Z-docosadienoic acid)	HMDB
CE(22:2(13Z,16Z))	Lipid Annotator

Chemical Formula

C₄₉H₈₄O₂

Average Mass

705.1901 Da

Monoisotopic Mass

704.64713 Da

IUPAC Name

(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (13Z,16Z)-docosa-13,16-dienoate

Traditional Name

(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (13Z,16Z)-docosa-13,16-dienoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C49H84O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h11-12,14-15,30,39-40,42-46H,7-10,13,16-29,31-38H2,1-6H3/b12-11-,15-14-/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1

InChI Key

YSGVSTJGBYXXIM-OVUVNFMNSA-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
Apis cerana	LOTUS Database	35616633

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	10.94	ALOGPS
logP	15.98	ChemAxon
logS	-8.1	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	25	ChemAxon
Refractivity	224.05 m³·mol⁻¹	ChemAxon
Polarizability	94.64 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

HMDB0006737

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024051

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02530

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477893

PDB ID

Not Available

ChEBI ID

88774

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate (NP0299018)

MOL for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

3D MOL for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

3D SDF for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

3D-SDF for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

PDB for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

3D PDB for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

SMILES for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

INCHI for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

Structure for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)

3D Structure for NP0299018 ((7s,9ar,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl (13z,16z)-docosa-13,16-dienoate)