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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 01:02:39 UTC

Update Date

2022-03-07 02:49:19 UTC

HMDB ID

HMDB0003598

Secondary Accession Numbers

HMDB03598

Metabolite Identification

Common Name

Retinyl ester

Description

Retinyl ester, also known as ester, retinyl, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Based on a literature review a significant number of articles have been published on Retinyl ester.

Structure

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

HMDB0003598
     RDKit          3D
Retinyl ester
 52 52  0  0  0  0  0  0  0  0999 V2000
    1.1688   -1.6762   -1.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.5107   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.0774   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -0.3997   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -0.0263   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147   -1.0520   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0317   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -1.2800    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592   -0.7042    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706    0.7898    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.1601    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    1.9193    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355    2.0847   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    0.0174   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -0.2239   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524    0.5342    0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227    0.1943    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.8875    1.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8049   -0.0503   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1737   -0.3795   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4355   -1.1115   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3516   -0.0212    0.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9174   -1.4718   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136   -2.2348   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481   -2.4089   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    1.0070    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873   -1.3843   -1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -0.6222    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -2.0680   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -1.9152   -2.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469   -0.1627   -2.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9662   -1.0788   -2.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495   -0.7546   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2551   -2.3370    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489   -1.1471    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -0.9050    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    1.2551    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    1.1497    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    2.6622    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    1.1852    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7042    2.5682    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    3.0448   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4933    2.3362   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1376    1.7590   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    0.7464    0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872   -0.9042   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.2613    1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443    0.1674    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.8296    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.6295    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3253   -1.2373   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2733   -0.1672   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 11  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 22 52  1  0
M  END


  Mrv0541 02231219462D          

 22 22  0  0  0  0            999 V2000
   17.7852  -15.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3562  -15.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857  -21.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6732  -21.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6417  -21.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2127  -19.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6417  -16.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4983  -21.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9273  -21.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2127  -21.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4983  -22.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9273  -22.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2127  -23.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0707  -15.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9273  -19.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3562  -16.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2127  -20.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0707  -16.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9273  -20.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6417  -19.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3562  -17.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6417  -18.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 14  2  0  0  0  0
  3  8  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 17  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 18  2  0  0  0  0
 16 21  1  0  0  0  0
 17 19  2  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003598

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

> <INCHI_KEY>
WWDMJSSVVPXVSV-YCNIQYBTSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.451

> <EXACT_MASS>
302.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.07067757171936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethylcyclohexyl)nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
6.35

> <JCHEM_LOGP>
5.463605017

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.936687619573186

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
97.2074

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retinyl ester

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0003598
     RDKit          3D
Retinyl ester
 52 52  0  0  0  0  0  0  0  0999 V2000
    1.1688   -1.6762   -1.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.5107   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.0774   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -0.3997   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -0.0263   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147   -1.0520   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0317   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -1.2800    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592   -0.7042    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706    0.7898    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.1601    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    1.9193    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355    2.0847   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    0.0174   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -0.2239   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524    0.5342    0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227    0.1943    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.8875    1.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8049   -0.0503   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1737   -0.3795   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4355   -1.1115   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3516   -0.0212    0.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9174   -1.4718   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136   -2.2348   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481   -2.4089   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    1.0070    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873   -1.3843   -1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -0.6222    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -2.0680   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -1.9152   -2.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469   -0.1627   -2.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9662   -1.0788   -2.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495   -0.7546   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2551   -2.3370    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489   -1.1471    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -0.9050    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    1.2551    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    1.1497    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    2.6622    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    1.1852    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7042    2.5682    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    3.0448   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4933    2.3362   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1376    1.7590   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    0.7464    0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872   -0.9042   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.2613    1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443    0.1674    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.8296    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.6295    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3253   -1.2373   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2733   -0.1672   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 11  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 22 52  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      33.199 -28.635   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.532 -28.635   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      24.427 -39.621   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.657 -40.955   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.198 -40.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.530 -35.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.198 -30.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.197 -40.955   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.864 -40.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.530 -40.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.197 -42.495   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.864 -42.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.530 -43.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.865 -29.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.864 -36.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.532 -31.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.530 -38.645   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.865 -30.945   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.864 -37.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      29.198 -35.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.532 -33.255   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.198 -34.025   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    8                                                            
CONECT    4    8                                                            
CONECT    5    9                                                            
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8    3    4   10   11                                             
CONECT    9    5   10   12                                                  
CONECT   10    8    9   17                                                  
CONECT   11    8   13                                                       
CONECT   12    9   13                                                       
CONECT   13   11   12                                                       
CONECT   14    1    2   18                                                  
CONECT   15    6   19   20                                                  
CONECT   16    7   18   21                                                  
CONECT   17   10   19                                                       
CONECT   18   14   16                                                       
CONECT   19   15   17                                                       
CONECT   20   15   22                                                       
CONECT   21   16   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0003598
HETATM    1  C1  UNL     1       1.169  -1.676  -1.522  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.984  -0.511  -0.596  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.310   0.077  -0.205  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.447  -0.400  -0.461  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.815  -0.026  -0.218  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.815  -1.052  -0.742  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.039  -1.032  -2.219  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.960  -1.280   0.151  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.659  -0.704   1.546  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.471   0.790   1.413  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.395   1.160   0.350  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.352   1.919   1.174  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.135   2.085  -0.533  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.064   0.017  -0.171  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.466  -0.224  -0.393  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.352   0.534   0.388  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.723   0.194   0.100  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.225   0.887   1.689  1.00  0.00           C  
HETATM   19  C19 UNL     1       6.805  -0.050  -0.102  1.00  0.00           C  
HETATM   20  C20 UNL     1       8.174  -0.379  -0.380  1.00  0.00           C  
HETATM   21  O1  UNL     1       8.436  -1.112  -1.457  1.00  0.00           O  
HETATM   22  O2  UNL     1       9.352  -0.021   0.328  1.00  0.00           O  
HETATM   23  H1  UNL     1       1.917  -1.472  -2.306  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.314  -2.235  -1.833  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.748  -2.409  -0.805  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.290   1.007   0.319  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.387  -1.384  -1.069  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.720  -0.622   0.924  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.228  -2.068  -0.617  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.616  -1.915  -2.617  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.547  -0.163  -2.649  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.966  -1.079  -2.667  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.850  -0.755  -0.234  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.255  -2.337   0.332  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.749  -1.147   1.944  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.443  -0.905   2.273  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.262   1.255   2.373  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.498   1.150   1.100  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.849   2.662   1.889  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.913   1.185   1.887  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.704   2.568   0.614  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.366   3.045  -0.017  1.00  0.00           H  
HETATM   43  H21 UNL     1      -3.493   2.336  -1.416  1.00  0.00           H  
HETATM   44  H22 UNL     1      -5.138   1.759  -0.933  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.878   0.746   0.687  1.00  0.00           H  
HETATM   46  H24 UNL     1       3.887  -0.904  -1.104  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.900   1.261   1.036  1.00  0.00           H  
HETATM   48  H26 UNL     1       5.644   0.167   2.292  1.00  0.00           H  
HETATM   49  H27 UNL     1       5.796   1.830   1.530  1.00  0.00           H  
HETATM   50  H28 UNL     1       7.242   0.629   1.762  1.00  0.00           H  
HETATM   51  H29 UNL     1       6.325  -1.237  -0.752  1.00  0.00           H  
HETATM   52  H30 UNL     1      10.273  -0.167  -0.145  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   14   14
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6   11   28
CONECT    6    7    8   29
CONECT    7   30   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   13
CONECT   12   39   40   41
CONECT   13   42   43   44
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   17   47
CONECT   17   18   19   19
CONECT   18   48   49   50
CONECT   19   20   51
CONECT   20   21   21   22
CONECT   22   52
END

HMDB0003598
     RDKit          3D
Retinyl ester
 52 52  0  0  0  0  0  0  0  0999 V2000
    1.1688   -1.6762   -1.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835   -0.5107   -0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    0.0774   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4474   -0.3997   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8147   -0.0263   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8147   -1.0520   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391   -1.0317   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -1.2800    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6592   -0.7042    1.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706    0.7898    1.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3948    1.1601    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    1.9193    1.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1355    2.0847   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0636    0.0174   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4661   -0.2239   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524    0.5342    0.3877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7227    0.1943    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2247    0.8875    1.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8049   -0.0503   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1737   -0.3795   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4355   -1.1115   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3516   -0.0212    0.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9174   -1.4718   -2.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136   -2.2348   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481   -2.4089   -0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901    1.0070    0.3193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873   -1.3843   -1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201   -0.6222    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -2.0680   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6162   -1.9152   -2.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469   -0.1627   -2.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9662   -1.0788   -2.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495   -0.7546   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2551   -2.3370    0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489   -1.1471    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4431   -0.9050    2.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2624    1.2551    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    1.1497    1.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    2.6622    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    1.1852    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7042    2.5682    0.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3658    3.0448   -0.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4933    2.3362   -1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1376    1.7590   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779    0.7464    0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8872   -0.9042   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9001    1.2613    1.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443    0.1674    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7963    1.8296    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2416    0.6295    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3253   -1.2373   -0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2733   -0.1672   -0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  2 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 11  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 22 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ester, all-trans-retinyl	MeSH
all trans Retinyl esters	MeSH
Ester, retinyl	MeSH
all-trans-Retinyl esters	MeSH
Retinyl esters	MeSH
all trans Retinyl ester	MeSH
all-trans-Retinyl ester	MeSH
56-Dihydroretinoic acid	ChEMBL, HMDB
all-e-Retinoic acid	ChEMBL, HMDB
56-Dihydroretinoate	Generator, HMDB
all-e-Retinoate	Generator, HMDB

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Weight

302.451

Monoisotopic Molecular Weight

302.224580204

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethylcyclohexyl)nona-2,4,6,8-tetraenoic acid

Traditional Name

retinyl ester

CAS Registry Number

Not Available

SMILES

CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14,17-18H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

InChI Key

WWDMJSSVVPXVSV-YCNIQYBTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Idiopathic intracranial hypertension (HMDB: HMDB0003598)
Osteoporosis (HMDB: HMDB0003598)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0003598)
Cell membrane (HMDB: HMDB0003598)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 10496276)

Tissue substructure

Adipose tissue (HMDB: HMDB0003598)
Epidermis (HMDB: HMDB0003598)

Tissue

Connective tissue

Adipose Tissue (HMDB: HMDB0003598)

Epithelium

Epidermis (HMDB: HMDB0003598)

Organ

Kidney (HMDB: HMDB0003598)
Liver (HMDB: HMDB0003598)

Cellular substructure

Membrane (HMDB: HMDB0003598)
Extracellular (HMDB: HMDB0003598)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003598)

Source

Endogenous

Endogenous (HMDB: HMDB0003598)

Animal

Animal (HMDB: HMDB0003598)

Exogenous

Food

Food (HMDB: HMDB0003598)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Chicken (FooDB: FOOD00329)
Greylag goose (FooDB: FOOD00368)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Guinea hen (FooDB: FOOD00373)
Velvet duck (FooDB: FOOD00427)
Ostrich (FooDB: FOOD00422)

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003598)

Nutrient

Nutrient (HMDB: HMDB0003598)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003598)

Emulsifier (HMDB: HMDB0003598)

Pharmaceutical industry

Biomarker

Hypertension (MarkerDB: MDB00030008)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00088 g/L	ALOGPS
logP	6.35	ALOGPS
logP	5.46	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.21 m³·mol⁻¹	ChemAxon
Polarizability	37.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.234	31661259
DarkChem	[M-H]-	176.814	31661259
DeepCCS	[M+H]+	193.476	30932474
DeepCCS	[M-H]-	191.118	30932474
DeepCCS	[M-2H]-	224.004	30932474
DeepCCS	[M+Na]+	199.569	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	175.5	32859911
AllCCS	[M+NH4]+	181.6	32859911
AllCCS	[M+Na]+	182.4	32859911
AllCCS	[M-H]-	182.7	32859911
AllCCS	[M+Na-2H]-	183.5	32859911
AllCCS	[M+HCOO]-	184.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retinyl ester	CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O	3614.0	Standard polar	33892256
Retinyl ester	CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O	2392.9	Standard non polar	33892256
Retinyl ester	CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O	2479.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retinyl ester,1TMS,isomer #1	CC(/C=C/C1C(C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C	2577.2	Semi standard non polar	33892256
Retinyl ester,1TBDMS,isomer #1	CC(/C=C/C1C(C)CCCC1(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C	2794.7	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 ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-3190000000-6350942f5f337f0854aa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl ester GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-6139000000-103432f8455b3f1da15a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl ester GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 ester 10V, Positive-QTOF	splash10-000i-0392000000-fd2bcaee3a8aa8ef1f91	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 20V, Positive-QTOF	splash10-000l-0940000000-d999454a4951b513e106	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 40V, Positive-QTOF	splash10-000i-5900000000-68bb39576638ee359ad1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 10V, Negative-QTOF	splash10-0zfr-0079000000-64d539d74e51ded7a105	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 20V, Negative-QTOF	splash10-0pc0-0094000000-9aa61625fad564fa1e56	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 40V, Negative-QTOF	splash10-052o-2590000000-44b65d0b69f1051e637a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 10V, Negative-QTOF	splash10-0udi-0149000000-a038329babc7de684b42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 20V, Negative-QTOF	splash10-0zfr-0393000000-57c7f4184a75a62e820f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 40V, Negative-QTOF	splash10-016r-4930000000-63ec76ed5f13c9770097	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 10V, Positive-QTOF	splash10-0zgr-0973000000-ce5e32df9099194f4779	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 20V, Positive-QTOF	splash10-00yi-3930000000-75c848c7071e888d4488	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl ester 40V, Positive-QTOF	splash10-0103-7900000000-2e43c6610f1ab346d1e6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Epidermis
Kidney
Liver

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	0.055 +/- 0.04 uM	Adult (>18 years old)	Female	Normal	17158416	details
Blood	Detected and Quantified	0.15 (0.03-0.046) uM	Adult (>18 years old)	Both	Normal	10496276	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.054 +/- 0.035 uM	Adult (>18 years old)	Female	Osteoporosis	17158416	details
Blood	Detected and Quantified	0.2 (0.03 - 0.5) uM	Adult (>18 years old)	Both	Idiopathic intracranial hypertension	10496276	details

Associated Disorders and Diseases

Disease References

Idiopathic intracranial hypertension
Jacobson DM, Berg R, Wall M, Digre KB, Corbett JJ, Ellefson RD: Serum vitamin A concentration is elevated in idiopathic intracranial hypertension. Neurology. 1999 Sep 22;53(5):1114-8. [PubMed:10496276 ]
Osteoporosis
Penniston KL, Weng N, Binkley N, Tanumihardjo SA: Serum retinyl esters are not elevated in postmenopausal women with and without osteoporosis whose preformed vitamin A intakes are high. Am J Clin Nutr. 2006 Dec;84(6):1350-6. [PubMed:17158416 ]

Associated OMIM IDs

243200 (Idiopathic intracranial hypertension)
166710 (Osteoporosis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023204

KNApSAcK ID

Not Available

Chemspider ID

10607936

KEGG Compound ID

C02075

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6966

PubChem Compound

5460164

PDB ID

Not Available

ChEBI ID

545914

Food Biomarker Ontology

Not Available

VMH ID

M02838

MarkerDB ID

MDB00030008

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mills JP, Penniston KL, Tanumihardjo SA: Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. Int J Vitam Nutr Res. 2005 Mar;75(2):126-32. [PubMed:15929633 ]
Zilversmit DB, Morton RE, Hughes LB, Thompson KH: Exchange of retinyl and cholesteryl esters between lipoproteins of rabbit plasma. Biochim Biophys Acta. 1982 Jul 20;712(1):88-93. [PubMed:7115749 ]
Kang S, Duell EA, Fisher GJ, Datta SC, Wang ZQ, Reddy AP, Tavakkol A, Yi JY, Griffiths CE, Elder JT, et al.: Application of retinol to human skin in vivo induces epidermal hyperplasia and cellular retinoid binding proteins characteristic of retinoic acid but without measurable retinoic acid levels or irritation. J Invest Dermatol. 1995 Oct;105(4):549-56. [PubMed:7561157 ]
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 ]
Stauber PM, Sherry B, VanderJagt DJ, Bhagavan HN, Garry PJ: A longitudinal study of the relationship between vitamin A supplementation and plasma retinol, retinyl esters, and liver enzyme activities in a healthy elderly population. Am J Clin Nutr. 1991 Nov;54(5):878-83. [PubMed:1951160 ]
Got L, Gousson T, Delacoux E: Simultaneous determination of retinyl esters and retinol in human livers by reversed-phase high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1995 Jun 23;668(2):233-9. [PubMed:7581858 ]

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

Acyl-CoA + Vitamin A → Coenzyme A + Retinyl ester	details

Enzyme Details

2. Retinoid isomerohydrolase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Plays important roles in the production of 11-cis retinal and in visual pigment regeneration. The soluble form binds vitamin A (all-trans-retinol), making it available for LRAT processing to all-trans-retinyl ester. The membrane form, palmitoylated by LRAT, binds all-trans-retinyl esters, making them available for IMH (isomerohydrolase) processing to all-cis-retinol. The soluble form is regenerated by transferring its palmitoyl groups onto 11-cis-retinol, a reaction catalyzed by LRAT. The enzymatic activity is linearly dependent of the expression levels and membrane association.
Gene Name:: RPE65
Uniprot ID:: Q16518
Molecular weight:: 60947.08

Enzyme Details

3. 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

4. Diacylglycerol O-acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides. Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides (By similarity). Functions also as an acyl-CoA retinol acyltransferase (ARAT).
Gene Name:: DGAT2
Uniprot ID:: Q96PD7
Molecular weight:: 39043.88

Reactions

Acyl-CoA + Vitamin A → Coenzyme A + Retinyl ester	details

Enzyme Details

5. 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

6. 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

Acyl-CoA + Vitamin A → Coenzyme A + Retinyl ester	details

Showing metabocard for Retinyl ester (HMDB0003598)

MOL for HMDB0003598 (Retinyl ester)

3D MOL for HMDB0003598 (Retinyl ester)

3D SDF for HMDB0003598 (Retinyl ester)

3D-SDF for HMDB0003598 (Retinyl ester)

PDB for HMDB0003598 (Retinyl ester)

3D PDB for HMDB0003598 (Retinyl ester)

SMILES for HMDB0003598 (Retinyl ester)

INCHI for HMDB0003598 (Retinyl ester)

Structure for HMDB0003598 (Retinyl ester)

3D Structure for HMDB0003598 (Retinyl ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions