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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 02:31:31 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003648

Secondary Accession Numbers

HMDB03648

Metabolite Identification

Common Name

Retinyl palmitate

Description

Retinyl palmitate, or vitamin A palmitate, is a common vitamin supplement, with formula C36H60O2. It is available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol and Palmitate. Retinyl palmitate is an alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231219462D          

 38 38  0  0  0  0            999 V2000
   17.9274  -15.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6553  -14.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3619  -15.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6429  -15.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0718  -15.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9329  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7908  -15.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2140  -15.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5007  -15.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5041  -15.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2196  -15.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7852  -15.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9296  -15.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0752  -15.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6485  -15.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3563  -15.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2174  -15.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3585  -15.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4931  -14.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6682  -14.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7975  -14.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9396  -14.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4840  -16.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0730  -14.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3541  -15.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3451  -16.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0551  -16.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6463  -15.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7885  -15.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9307  -15.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4985  -15.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6407  -15.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0696  -15.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3597  -15.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2118  -15.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5018  -14.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7740  -16.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7829  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 28  1  0  0  0  0
  2 28  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 28  1  0  0  0  0
 17 31  1  0  0  0  0
 19 24  1  0  0  0  0
 20 24  1  0  0  0  0
 21 29  1  0  0  0  0
 22 30  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  1  0  0  0  0
 24 38  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 37  1  0  0  0  0
 29 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 30 35  1  0  0  0  0
 32 34  1  0  0  0  0
 33 34  2  0  0  0  0
 35 36  2  0  0  0  0
 36 38  1  0  0  0  0
 37 38  2  0  0  0  0
M  END

HMDB0003648
     RDKit          3D
Retinyl palmitate
 98 98  0  0  0  0  0  0  0  0999 V2000
   13.1048    3.9892   -0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7911    2.5933   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3171    2.2728   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3407   -2.3992    1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2629   -2.7229    2.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1122   -1.9373    3.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2514   -1.9981    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520   -1.4219    1.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -1.4603    2.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.7853    0.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232   -0.2769    1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723    0.3568    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4303    0.5522    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3935    0.1198   -0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.0798    0.5890   -2.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7697    1.1875   -3.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9958    1.6934   -2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9559    2.6266   -1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6727    4.1107    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38 98  1  0
M  END


  Mrv0541 02231219462D          

 38 38  0  0  0  0            999 V2000
   17.9274  -15.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6553  -14.2465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3619  -15.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6429  -15.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0718  -15.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9329  -15.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7908  -15.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2140  -15.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5007  -15.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5041  -15.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.9296  -15.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0752  -15.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6485  -15.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3563  -15.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2174  -15.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3585  -15.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4931  -14.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6682  -14.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7975  -14.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9396  -14.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4840  -16.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0730  -14.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3541  -15.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3451  -16.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0551  -16.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6463  -15.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7885  -15.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9307  -15.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4985  -15.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6407  -15.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0696  -15.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3597  -15.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2118  -15.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5018  -14.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7740  -16.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7829  -15.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  1 28  1  0  0  0  0
  2 28  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
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 16 28  1  0  0  0  0
 17 31  1  0  0  0  0
 19 24  1  0  0  0  0
 20 24  1  0  0  0  0
 21 29  1  0  0  0  0
 22 30  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  1  0  0  0  0
 24 38  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 37  1  0  0  0  0
 29 31  2  0  0  0  0
 29 33  1  0  0  0  0
 30 32  2  0  0  0  0
 30 35  1  0  0  0  0
 32 34  1  0  0  0  0
 33 34  2  0  0  0  0
 35 36  2  0  0  0  0
 36 38  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003648

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

> <INCHI_KEY>
VYGQUTWHTHXGQB-FFHKNEKCSA-N

> <FORMULA>
C36H60O2

> <MOLECULAR_WEIGHT>
524.8604

> <EXACT_MASS>
524.459331164

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
70.50311302463982

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate

> <ALOGPS_LOGP>
10.12

> <JCHEM_LOGP>
11.615147075333335

> <ALOGPS_LOGS>
-6.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.04338460696517

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
171.5148

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.07e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitamin a palmitate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003648
     RDKit          3D
Retinyl palmitate
 98 98  0  0  0  0  0  0  0  0999 V2000
   13.1048    3.9892   -0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7911    2.5933   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3171    2.2728   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0022    0.8820   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5449    0.5101   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2126    0.5379    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    0.1858    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4230   -1.1777   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2450   -2.2269    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -2.3992    1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1122   -1.9373    3.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4986   -1.2828    1.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303    0.5522    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4659   -0.5343   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3946    1.5901    0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0835    0.9678   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3447   -1.3929   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9767   -3.2621    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544   -1.4440    2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2283   -3.1404    2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9261   -3.8049    2.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7900   -3.0483    3.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -0.9555    3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6356   -2.4209    4.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3026   -0.6325    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -0.9860    2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0495   -3.0699    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -3.2755    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.1563    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -2.7668    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832    0.5404    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -1.0475    2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    1.2176    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4561   -1.7759    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -2.0730    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9961   -1.6429    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.4115   -0.8114   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 38 98  1  0
M  END

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      33.464 -28.889   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      34.823 -26.593   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      45.476 -28.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      44.133 -29.005   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      46.801 -29.033   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.808 -28.220   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      48.143 -28.278   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.466 -28.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.468 -29.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.141 -28.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      50.810 -28.307   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.799 -28.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.135 -29.091   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.474 -28.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      53.477 -28.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.132 -28.918   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.139 -28.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      54.803 -29.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.587 -26.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.047 -26.618   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.489 -26.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.154 -26.478   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.437 -31.069   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.803 -27.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.461 -28.715   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.444 -30.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.770 -31.040   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.806 -28.133   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      29.472 -28.076   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.137 -28.018   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.797 -28.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.463 -28.802   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.130 -28.831   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.805 -28.047   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.795 -28.773   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.470 -27.989   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      20.111 -30.284   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      20.128 -28.744   0.000  0.00  0.00           C+0
CONECT    1   17   28                                                       
CONECT    2   28                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   18                                                       
CONECT   16   14   28                                                       
CONECT   17    1   31                                                       
CONECT   18   15                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21   29                                                            
CONECT   22   30                                                            
CONECT   23   37                                                            
CONECT   24   19   20   25   38                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   37                                                       
CONECT   28    1    2   16                                                  
CONECT   29   21   31   33                                                  
CONECT   30   22   32   35                                                  
CONECT   31   17   29                                                       
CONECT   32   30   34                                                       
CONECT   33   29   34                                                       
CONECT   34   32   33                                                       
CONECT   35   30   36                                                       
CONECT   36   35   38                                                       
CONECT   37   23   27   38                                                  
CONECT   38   24   36   37                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   76    0
END

COMPND    HMDB0003648
HETATM    1  C1  UNL     1      13.105   3.989  -0.897  1.00  0.00           C  
HETATM    2  C2  UNL     1      12.791   2.593  -1.377  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.317   2.273  -1.104  1.00  0.00           C  
HETATM    4  C4  UNL     1      11.002   0.882  -1.584  1.00  0.00           C  
HETATM    5  C5  UNL     1       9.545   0.510  -1.332  1.00  0.00           C  
HETATM    6  C6  UNL     1       9.213   0.538   0.121  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.789   0.186   0.385  1.00  0.00           C  
HETATM    8  C8  UNL     1       7.423  -1.178  -0.103  1.00  0.00           C  
HETATM    9  C9  UNL     1       8.245  -2.227   0.504  1.00  0.00           C  
HETATM   10  C10 UNL     1       8.341  -2.399   1.943  1.00  0.00           C  
HETATM   11  C11 UNL     1       7.263  -2.723   2.848  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.112  -1.937   3.207  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.050  -1.472   2.308  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.351  -2.549   1.541  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.251  -1.998   0.685  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.152  -1.422   1.481  1.00  0.00           C  
HETATM   17  O1  UNL     1       2.107  -1.460   2.744  1.00  0.00           O  
HETATM   18  O2  UNL     1       1.060  -0.785   0.846  1.00  0.00           O  
HETATM   19  C17 UNL     1       0.023  -0.277   1.672  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.072   0.357   0.944  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.342  -0.100   1.020  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.499  -1.283   1.891  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.430   0.552   0.320  1.00  0.00           C  
HETATM   24  C22 UNL     1      -4.641   0.089   0.399  1.00  0.00           C  
HETATM   25  C23 UNL     1      -5.821   0.646  -0.248  1.00  0.00           C  
HETATM   26  C24 UNL     1      -7.018   0.069  -0.105  1.00  0.00           C  
HETATM   27  C25 UNL     1      -7.033  -1.140   0.735  1.00  0.00           C  
HETATM   28  C26 UNL     1      -8.207   0.654  -0.753  1.00  0.00           C  
HETATM   29  C27 UNL     1      -9.393   0.120  -0.647  1.00  0.00           C  
HETATM   30  C28 UNL     1     -10.652   0.535  -1.195  1.00  0.00           C  
HETATM   31  C29 UNL     1     -11.747  -0.248  -0.913  1.00  0.00           C  
HETATM   32  C30 UNL     1     -11.522  -1.447  -0.070  1.00  0.00           C  
HETATM   33  C31 UNL     1     -13.086   0.100  -1.432  1.00  0.00           C  
HETATM   34  C32 UNL     1     -13.080   0.589  -2.844  1.00  0.00           C  
HETATM   35  C33 UNL     1     -11.770   1.187  -3.240  1.00  0.00           C  
HETATM   36  C34 UNL     1     -10.996   1.693  -2.007  1.00  0.00           C  
HETATM   37  C35 UNL     1     -11.956   2.627  -1.241  1.00  0.00           C  
HETATM   38  C36 UNL     1      -9.895   2.531  -2.525  1.00  0.00           C  
HETATM   39  H1  UNL     1      12.673   4.111   0.115  1.00  0.00           H  
HETATM   40  H2  UNL     1      14.197   4.149  -0.882  1.00  0.00           H  
HETATM   41  H3  UNL     1      12.674   4.772  -1.558  1.00  0.00           H  
HETATM   42  H4  UNL     1      13.410   1.902  -0.757  1.00  0.00           H  
HETATM   43  H5  UNL     1      12.967   2.486  -2.449  1.00  0.00           H  
HETATM   44  H6  UNL     1      11.161   2.352  -0.020  1.00  0.00           H  
HETATM   45  H7  UNL     1      10.713   2.989  -1.698  1.00  0.00           H  
HETATM   46  H8  UNL     1      11.182   0.758  -2.667  1.00  0.00           H  
HETATM   47  H9  UNL     1      11.609   0.135  -0.991  1.00  0.00           H  
HETATM   48  H10 UNL     1       8.897   1.192  -1.909  1.00  0.00           H  
HETATM   49  H11 UNL     1       9.466  -0.534  -1.732  1.00  0.00           H  
HETATM   50  H12 UNL     1       9.395   1.590   0.466  1.00  0.00           H  
HETATM   51  H13 UNL     1       9.907  -0.165   0.667  1.00  0.00           H  
HETATM   52  H14 UNL     1       7.607   0.208   1.501  1.00  0.00           H  
HETATM   53  H15 UNL     1       7.084   0.968  -0.007  1.00  0.00           H  
HETATM   54  H16 UNL     1       6.345  -1.393  -0.176  1.00  0.00           H  
HETATM   55  H17 UNL     1       7.705  -1.164  -1.253  1.00  0.00           H  
HETATM   56  H18 UNL     1       9.332  -2.048   0.126  1.00  0.00           H  
HETATM   57  H19 UNL     1       7.977  -3.262   0.025  1.00  0.00           H  
HETATM   58  H20 UNL     1       8.854  -1.444   2.401  1.00  0.00           H  
HETATM   59  H21 UNL     1       9.228  -3.140   2.160  1.00  0.00           H  
HETATM   60  H22 UNL     1       6.926  -3.805   2.541  1.00  0.00           H  
HETATM   61  H23 UNL     1       7.790  -3.048   3.862  1.00  0.00           H  
HETATM   62  H24 UNL     1       6.529  -0.956   3.693  1.00  0.00           H  
HETATM   63  H25 UNL     1       5.636  -2.421   4.155  1.00  0.00           H  
HETATM   64  H26 UNL     1       5.303  -0.632   1.649  1.00  0.00           H  
HETATM   65  H27 UNL     1       4.246  -0.986   2.995  1.00  0.00           H  
HETATM   66  H28 UNL     1       5.050  -3.070   0.857  1.00  0.00           H  
HETATM   67  H29 UNL     1       3.931  -3.275   2.291  1.00  0.00           H  
HETATM   68  H30 UNL     1       3.644  -1.156   0.053  1.00  0.00           H  
HETATM   69  H31 UNL     1       2.798  -2.767   0.030  1.00  0.00           H  
HETATM   70  H32 UNL     1       0.483   0.540   2.311  1.00  0.00           H  
HETATM   71  H33 UNL     1      -0.268  -1.047   2.385  1.00  0.00           H  
HETATM   72  H34 UNL     1      -0.929   1.218   0.313  1.00  0.00           H  
HETATM   73  H35 UNL     1      -2.230  -1.082   2.962  1.00  0.00           H  
HETATM   74  H36 UNL     1      -3.456  -1.776   1.886  1.00  0.00           H  
HETATM   75  H37 UNL     1      -1.768  -2.073   1.509  1.00  0.00           H  
HETATM   76  H38 UNL     1      -3.290   1.438  -0.291  1.00  0.00           H  
HETATM   77  H39 UNL     1      -4.810  -0.796   1.008  1.00  0.00           H  
HETATM   78  H40 UNL     1      -5.729   1.541  -0.842  1.00  0.00           H  
HETATM   79  H41 UNL     1      -7.996  -1.643   0.833  1.00  0.00           H  
HETATM   80  H42 UNL     1      -6.736  -0.845   1.770  1.00  0.00           H  
HETATM   81  H43 UNL     1      -6.336  -1.922   0.332  1.00  0.00           H  
HETATM   82  H44 UNL     1      -8.099   1.541  -1.320  1.00  0.00           H  
HETATM   83  H45 UNL     1      -9.412  -0.811  -0.010  1.00  0.00           H  
HETATM   84  H46 UNL     1     -12.469  -2.000   0.120  1.00  0.00           H  
HETATM   85  H47 UNL     1     -10.802  -2.099  -0.605  1.00  0.00           H  
HETATM   86  H48 UNL     1     -11.147  -1.142   0.919  1.00  0.00           H  
HETATM   87  H49 UNL     1     -13.695   0.708  -0.727  1.00  0.00           H  
HETATM   88  H50 UNL     1     -13.643  -0.891  -1.455  1.00  0.00           H  
HETATM   89  H51 UNL     1     -13.396  -0.225  -3.564  1.00  0.00           H  
HETATM   90  H52 UNL     1     -13.892   1.344  -2.939  1.00  0.00           H  
HETATM   91  H53 UNL     1     -11.116   0.431  -3.718  1.00  0.00           H  
HETATM   92  H54 UNL     1     -11.916   2.001  -3.976  1.00  0.00           H  
HETATM   93  H55 UNL     1     -12.895   2.680  -1.787  1.00  0.00           H  
HETATM   94  H56 UNL     1     -11.544   3.670  -1.227  1.00  0.00           H  
HETATM   95  H57 UNL     1     -12.012   2.313  -0.191  1.00  0.00           H  
HETATM   96  H58 UNL     1      -9.207   2.015  -3.203  1.00  0.00           H  
HETATM   97  H59 UNL     1     -10.431   3.259  -3.271  1.00  0.00           H  
HETATM   98  H60 UNL     1      -9.474   3.235  -1.807  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   42   43
CONECT    3    4   44   45
CONECT    4    5   46   47
CONECT    5    6   48   49
CONECT    6    7   50   51
CONECT    7    8   52   53
CONECT    8    9   54   55
CONECT    9   10   56   57
CONECT   10   11   58   59
CONECT   11   12   60   61
CONECT   12   13   62   63
CONECT   13   14   64   65
CONECT   14   15   66   67
CONECT   15   16   68   69
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   70   71
CONECT   20   21   21   72
CONECT   21   22   23
CONECT   22   73   74   75
CONECT   23   24   24   76
CONECT   24   25   77
CONECT   25   26   26   78
CONECT   26   27   28
CONECT   27   79   80   81
CONECT   28   29   29   82
CONECT   29   30   83
CONECT   30   31   31   36
CONECT   31   32   33
CONECT   32   84   85   86
CONECT   33   34   87   88
CONECT   34   35   89   90
CONECT   35   36   91   92
CONECT   36   37   38
CONECT   37   93   94   95
CONECT   38   96   97   98
END

HMDB0003648
     RDKit          3D
Retinyl palmitate
 98 98  0  0  0  0  0  0  0  0999 V2000
   13.1048    3.9892   -0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7911    2.5933   -1.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3171    2.2728   -1.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0022    0.8820   -1.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5449    0.5101   -1.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2126    0.5379    0.1209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7890    0.1858    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4230   -1.1777   -0.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2450   -2.2269    0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407   -2.3992    1.9432 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2629   -2.7229    2.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1122   -1.9373    3.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0502   -1.4723    2.3085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.5494    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2514   -1.9981    0.6848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520   -1.4219    1.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1074   -1.4603    2.7437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0602   -0.7853    0.8459 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232   -0.2769    1.6717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723    0.3568    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3416   -0.0998    1.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986   -1.2828    1.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4303    0.5522    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6410    0.0890    0.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8214    0.6458   -0.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0176    0.0688   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0329   -1.1397    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2065    0.6539   -0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3935    0.1198   -0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6521    0.5354   -1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7467   -0.2478   -0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5220   -1.4466   -0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0860    0.1003   -1.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0798    0.5890   -2.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7697    1.1875   -3.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9958    1.6934   -2.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9559    2.6266   -1.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8949    2.5310   -2.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6727    4.1107    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1970    4.1487   -0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740    4.7720   -1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4101    1.9023   -0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9671    2.4855   -2.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1610    2.3521   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7125    2.9892   -1.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1818    0.7581   -2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6090    0.1348   -0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8969    1.1919   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4659   -0.5343   -1.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3946    1.5901    0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9071   -0.1647    0.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6072    0.2083    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0835    0.9678   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3447   -1.3929   -0.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7045   -1.1635   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3321   -2.0478    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9767   -3.2621    0.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8544   -1.4440    2.4012 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2283   -3.1404    2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9261   -3.8049    2.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7900   -3.0483    3.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5288   -0.9555    3.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6356   -2.4209    4.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3026   -0.6325    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458   -0.9860    2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0495   -3.0699    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9313   -3.2755    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.1563    0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -2.7668    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4832    0.5404    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -1.0475    2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286    1.2176    0.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304   -1.0820    2.9622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.7759    1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683   -2.0730    1.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2902    1.4378   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -0.7958    1.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7291    1.5412   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9961   -1.6429    0.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7363   -0.8448    1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3363   -1.9223    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0988    1.5408   -1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4115   -0.8114   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4690   -1.9999    0.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8020   -2.0994   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1473   -1.1424    0.9193 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6946    0.7084   -0.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6432   -0.8911   -1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3960   -0.2254   -3.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8919    1.3436   -2.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1156    0.4308   -3.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9165    2.0006   -3.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8955    2.6798   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5436    3.6699   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0117    2.3134   -0.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2066    2.0150   -3.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4308    3.2588   -3.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4743    3.2349   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6  7  1  0
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 38 98  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoate	ChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoic acid ester	ChEBI
Afaxin	ChEBI
all-trans-Retinol palmitate	ChEBI
all-trans-Retinyl hexadecanoate	ChEBI
Alphalin	ChEBI
Aquasol a	ChEBI
Arovit	ChEBI
Chocola a	ChEBI
O(15)-Hexadecanoylretinol	ChEBI
Optovit-a	ChEBI
Retinol hexadecanoate	ChEBI
Retinol palmitate	ChEBI
Retinyl hexadecanoate	ChEBI
trans-Retinol palmitate	ChEBI
trans-Retinyl palmitate	ChEBI
Vitamin a palmitate	ChEBI
all-trans-Retinyl palmitate	Kegg
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl hexadecanoic acid	Generator
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8,tetraenyl hexadecanoate ester	Generator
all-trans-Retinol palmitic acid	Generator
all-trans-Retinyl hexadecanoic acid	Generator
Retinol hexadecanoic acid	Generator
Retinol palmitic acid	Generator
Retinyl hexadecanoic acid	Generator
trans-Retinol palmitic acid	Generator
trans-Retinyl palmitic acid	Generator
Vitamin a palmitic acid	Generator
all-trans-Retinyl palmitic acid	Generator
Retinyl palmitic acid	Generator
all-trans-Vitamin a palmitate	HMDB
Aquapalm	HMDB
Axerophthol palmitate	HMDB
Dispatabs tabs	HMDB
Ester found in fish liver oils	HMDB
Lutavit a 500 plus	HMDB
Myvak	HMDB
Myvax	HMDB
Optovit a	HMDB
Testavol S	HMDB
Vitazyme a	HMDB

Chemical Formula

C₃₆H₆₀O₂

Average Molecular Weight

524.8604

Monoisotopic Molecular Weight

524.459331164

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl hexadecanoate

Traditional Name

vitamin a palmitate

CAS Registry Number

79-81-2

SMILES

CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

InChI Key

VYGQUTWHTHXGQB-FFHKNEKCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as wax monoesters. These are waxes bearing an ester group at exactly one position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Wax monoesters

Alternative Parents

Substituents

Wax monoester skeleton
Retinoid skeleton
Diterpenoid
Fatty alcohol ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinyl palmitate (CHEBI:17616 )
Retinoids (C02588 )
Retinoids (LMPR01090013 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	28.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.8e-11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.1e-05 g/L	ALOGPS
logP	10.12	ALOGPS
logP	11.62	ChemAxon
logS	-6.8	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	21	ChemAxon
Refractivity	171.51 m³·mol⁻¹	ChemAxon
Polarizability	70.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	238.683	31661259
DarkChem	[M-H]-	239.919	31661259
DeepCCS	[M+H]+	244.817	30932474
DeepCCS	[M-H]-	242.421	30932474
DeepCCS	[M-2H]-	275.304	30932474
DeepCCS	[M+Na]+	251.434	30932474
AllCCS	[M+H]+	240.9	32859911
AllCCS	[M+H-H2O]+	239.9	32859911
AllCCS	[M+NH4]+	241.9	32859911
AllCCS	[M+Na]+	242.2	32859911
AllCCS	[M-H]-	215.6	32859911
AllCCS	[M+Na-2H]-	220.4	32859911
AllCCS	[M+HCOO]-	225.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retinyl palmitate	CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	4434.3	Standard polar	33892256
Retinyl palmitate	CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3730.3	Standard non polar	33892256
Retinyl palmitate	CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3967.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl palmitate GC-MS (Non-derivatized) - 70eV, Positive	splash10-07vr-6590330000-c4a001ec8772bbd8b673	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 10V, Positive-QTOF	splash10-00n0-0391040000-4bcb419b1aa363c5a184	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 20V, Positive-QTOF	splash10-00kr-3890000000-13b63fb441c04d797a5a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 40V, Positive-QTOF	splash10-053i-4910200000-ec9d8c6e06e67e406eae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 10V, Negative-QTOF	splash10-00dr-0090050000-063ec803b899247ff625	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 20V, Negative-QTOF	splash10-0a4r-0090000000-ceacddaa1af7bfe01b93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 40V, Negative-QTOF	splash10-052u-2090000000-010cffd7fdb5e0c0ae62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 10V, Positive-QTOF	splash10-00or-0970350000-ae98e4da36c7fef49b01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 20V, Positive-QTOF	splash10-00kr-1960010000-e463420790c3679b3761	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 40V, Positive-QTOF	splash10-01b9-3930000000-2209374e0a45d158da93	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 10V, Negative-QTOF	splash10-00di-0060090000-71bf924b1d2a2be5b8a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 20V, Negative-QTOF	splash10-0a4i-0090010000-5bffb18764c70498c127	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl palmitate 40V, Negative-QTOF	splash10-0a4l-9870000000-8e1a1ac617c6db688b0b	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.105 +/- 0.109 uM	Adult (>18 years old)	Female	Normal	18813024	details
Blood	Detected and Quantified	0.0071 +/- 0.0048 uM	Adult (>18 years old)	Both	Normal	17009166	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DBSALT000855

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030671

KNApSAcK ID

Not Available

Chemspider ID

4444162

KEGG Compound ID

C02588

BioCyc ID

CHOCOLA_A

BiGG ID

Not Available

Wikipedia Link

Retinyl_palmitate

METLIN ID

Not Available

PubChem Compound

5280531

PDB ID

Not Available

ChEBI ID

17616

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1302861

References

Synthesis Reference

Ajima, Ayako; Takahashi, Katsunobu; Matsushima, Ayako; Saito, Yuji; Inada, Yuji. Retinyl esters synthesis by polyethylene glycol-modified lipase in benzene. Biotechnology Letters (1986), 8(8), 547-52.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Gylling H, Relas H, Miettinen HE, Radhakrishnan R, Miettinen TA: Delayed postprandial retinyl palmitate and squalene removal in a patient heterozygous for apolipoprotein A-IFIN mutation (Leu 159-->Arg) and low HDL cholesterol level without coronary artery disease. Atherosclerosis. 1996 Dec 20;127(2):239-43. [PubMed:9125314 ]
Relas H, Gylling H, Miettinen TA: Effect of stanol ester on postabsorptive squalene and retinyl palmitate. Metabolism. 2000 Apr;49(4):473-8. [PubMed:10778871 ]
Antille C, Tran C, Sorg O, Carraux P, Didierjean L, Saurat JH: Vitamin A exerts a photoprotective action in skin by absorbing ultraviolet B radiation. J Invest Dermatol. 2003 Nov;121(5):1163-7. [PubMed:14708621 ]
Epler KS, Ziegler RG, Craft NE: Liquid chromatographic method for the determination of carotenoids, retinoids and tocopherols in human serum and in food. J Chromatogr. 1993 Sep 8;619(1):37-48. [PubMed:8245162 ]
Ribaya-Mercado JD, Blanco MC, Fox JG, Russell RM: High concentrations of vitamin A esters circulate primarily as retinyl stearate and are stored primarily as retinyl palmitate in ferret tissues. J Am Coll Nutr. 1994 Feb;13(1):83-6. [PubMed:8157860 ]
Thomas JB, Kline MC, Schiller SB, Ellerbe PM, Sniegoski LT, Duewer DL, Sharpless KE: Certification of fat-soluble vitamins, carotenoids, and cholesterol in human serum: Standard Reference Material 968b. Anal Bioanal Chem. 1996 Aug;356(1):1-9. [PubMed:15045249 ]
Fernandez-Miranda C, Cancelas P, Sanz M, Porres A, Gamez Gerique J: Influence of apolipoprotein-E phenotypes on postprandial lipoprotein metabolism after three different fat loads. Nutrition. 2001 Jul-Aug;17(7-8):529-33. [PubMed:11448569 ]
Weintraub M, Grosskopf I, Trostanesky Y, Charach G, Rubinstein A, Stern N: Thyroxine replacement therapy enhances clearance of chylomicron remnants in patients with hypothyroidism. J Clin Endocrinol Metab. 1999 Jul;84(7):2532-6. [PubMed:10404832 ]
Lindstrom MB, Sternby B, Borgstrom B: Concerted action of human carboxyl ester lipase and pancreatic lipase during lipid digestion in vitro: importance of the physicochemical state of the substrate. Biochim Biophys Acta. 1988 Mar 25;959(2):178-84. [PubMed:3349096 ]
Gimeno A, Zaragoza R, Vivo-Sese I, Vina JR, Miralles VJ: Retinol, at concentrations greater than the physiological limit, induces oxidative stress and apoptosis in human dermal fibroblasts. Exp Dermatol. 2004 Jan;13(1):45-54. [PubMed:15009115 ]
Kobayashi TK, Tsubota K, Takamura E, Sawa M, Ohashi Y, Usui M: Effect of retinol palmitate as a treatment for dry eye: a cytological evaluation. Ophthalmologica. 1997;211(6):358-61. [PubMed:9380354 ]
Foger B, Drexel H, Hopferwieser T, Miesenbock G, Ritsch A, Lechleitner M, Trobinger G, Patsch JR: Fenofibrate improves postprandial chylomicron clearance in II B hyperlipoproteinemia. Clin Investig. 1994 Mar;72(4):294-301. [PubMed:8043977 ]
Van Lieshout M, West CE, Van De Bovenkamp P, Wang Y, Sun Y, Van Breemen RB, Muhilal DP, Verhoeven MA, Creemers AF, Lugtenburg J: Extraction of carotenoids from feces, enabling the bioavailability of beta-carotene to be studied in Indonesian children. J Agric Food Chem. 2003 Aug 13;51(17):5123-30. [PubMed:12903979 ]
Zampelas A, Ah-Sing E, Chakraboraty J, Murphy M, Peel A, Wright J, Williams CM: The use of retinyl palmitate to measure clearance of chylomicrons and chylomicron remnants following meals of different fatty acid compositions. Biochem Soc Trans. 1993 May;21(2):137S. [PubMed:8359391 ]
Hartmann S, Froescheis O, Ringenbach F, Wyss R, Bucheli F, Bischof S, Bausch J, Wiegand UW: Determination of retinol and retinyl esters in human plasma by high-performance liquid chromatography with automated column switching and ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2001 Feb 25;751(2):265-75. [PubMed:11236082 ]
Tzimas G, Collins MD, Burgin H, Hummler H, Nau H: Embryotoxic doses of vitamin A to rabbits result in low plasma but high embryonic concentrations of all-trans-retinoic acid: risk of vitamin A exposure in humans. J Nutr. 1996 Sep;126(9):2159-71. [PubMed:8814204 ]
Guerci B, Paul JL, Hadjadj S, Durlach V, Verges B, Attia N, Girard-Globa A, Drouin P: Analysis of the postprandial lipid metabolism: use of a 3-point test. Diabetes Metab. 2001 Sep;27(4 Pt 1):449-57. [PubMed:11547218 ]
de Bruin TW, Brouwer CB, van Linde-Sibenius Trip M, Jansen H, Erkelens DW: Different postprandial metabolism of olive oil and soybean oil: a possible mechanism of the high-density lipoprotein conserving effect of olive oil. Am J Clin Nutr. 1993 Oct;58(4):477-83. [PubMed:8379502 ]
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Enzymes

Enzyme Details

1. Diacylglycerol O-acyltransferase 1

General function:: Involved in diacylglycerol O-acyltransferase activity
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:: DGAT1
Uniprot ID:: O75907
Molecular weight:: 55277.735

Reactions

Palmityl-CoA + Vitamin A → Coenzyme A + Retinyl palmitate	details

Enzyme Details

2. Lecithin retinol acyltransferase

General function:: Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:: Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:: LRAT
Uniprot ID:: O95237
Molecular weight:: 25702.635

Enzyme Details

3. Acyl-CoA wax alcohol acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:: AWAT1
Uniprot ID:: Q58HT5
Molecular weight:: 37758.815

Enzyme Details

4. Acyl-CoA wax alcohol acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:: AWAT2
Uniprot ID:: Q6E213
Molecular weight:: 38093.25

Reactions

Palmityl-CoA + Vitamin A → Coenzyme A + Retinyl palmitate	details

Showing metabocard for Retinyl palmitate (HMDB0003648)

MOL for HMDB0003648 (Retinyl palmitate)

3D MOL for HMDB0003648 (Retinyl palmitate)

3D SDF for HMDB0003648 (Retinyl palmitate)

3D-SDF for HMDB0003648 (Retinyl palmitate)

PDB for HMDB0003648 (Retinyl palmitate)

3D PDB for HMDB0003648 (Retinyl palmitate)

SMILES for HMDB0003648 (Retinyl palmitate)

INCHI for HMDB0003648 (Retinyl palmitate)

Structure for HMDB0003648 (Retinyl palmitate)

3D Structure for HMDB0003648 (Retinyl palmitate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions