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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-06-16 13:14:51 UTC

Update Date

2022-03-07 02:51:23 UTC

HMDB ID

HMDB0012329

Secondary Accession Numbers

HMDB12329

Metabolite Identification

Common Name

4-Oxoretinol

Description

4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564 ]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846 ].

Structure

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

HMDB0012329
     RDKit          3D
4-Oxoretinol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.0471    2.0670    2.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749    0.7753    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.0496    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871    0.4317    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -0.1150    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.4936    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574    1.7847    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.0838   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    0.3962   -0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -0.2482   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.1763   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    1.4349   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.5770   -2.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.1434   -3.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -0.0096   -4.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -1.2878    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -1.0436   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331   -2.4331    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310   -1.8370    2.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727   -0.9307    2.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277    0.4887    2.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8428    1.3786    2.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783    2.6903    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    1.9081    3.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    2.6376    3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    1.4128    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -1.0300   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.7391    1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832    2.1434    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    2.5522    0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003   -1.0525   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3360   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3829   -1.2072   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.1561   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5378    1.3136   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0579    1.9725   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101   -1.5228   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8966   -1.0155   -2.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168    0.6904   -2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8800    0.7639   -4.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3411   -0.2420    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -0.6474   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2391   -1.9501   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -3.3819    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290   -2.3470   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -2.5361    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052   -1.9919    2.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -2.8150    1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7879   -1.1892    3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027   -1.0555    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END


  Mrv0541 02231216232D          

 22 22  0  0  0  0            999 V2000
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012329

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+

> <INCHI_KEY>
PLIUCYCUYQIBDZ-RMWYGNQTSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.4351

> <EXACT_MASS>
300.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69054164246209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
4.026809811666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.890472282116395

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.435617288805766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1707943115512176

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.61659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxoretinol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0012329
     RDKit          3D
4-Oxoretinol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.0471    2.0670    2.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749    0.7753    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.0496    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871    0.4317    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -0.1150    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.4936    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574    1.7847    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.0838   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    0.3962   -0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -0.2482   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.1763   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    1.4349   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.5770   -2.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.1434   -3.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -0.0096   -4.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -1.2878    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -1.0436   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331   -2.4331    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310   -1.8370    2.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727   -0.9307    2.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277    0.4887    2.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8428    1.3786    2.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783    2.6903    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    1.9081    3.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    2.6376    3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    1.4128    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -1.0300   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.7391    1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832    2.1434    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    2.5522    0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003   -1.0525   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3360   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3829   -1.2072   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.1561   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5378    1.3136   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0579    1.9725   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101   -1.5228   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8966   -1.0155   -2.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168    0.6904   -2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8800    0.7639   -4.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3411   -0.2420    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -0.6474   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2391   -1.9501   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -3.3819    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290   -2.3470   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -2.5361    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052   -1.9919    2.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -2.8150    1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7879   -1.1892    3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027   -1.0555    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  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  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0012329
HETATM    1  C1  UNL     1      -3.047   2.067   2.538  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.675   0.775   2.085  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.919  -0.050   1.305  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.587   0.432   1.004  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.656  -0.115   0.276  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.675   0.494   0.055  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.957   1.785   0.703  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.572  -0.084  -0.678  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.902   0.396  -0.976  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.760  -0.248  -1.729  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.102   0.176  -2.066  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.650   1.435  -1.572  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.866  -0.577  -2.840  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.217  -0.143  -3.174  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.336  -0.010  -4.562  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.571  -1.288   0.916  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.661  -1.044  -0.141  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.733  -2.433   0.438  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.331  -1.837   2.153  1.00  0.00           C  
HETATM   20  C19 UNL     1      -5.473  -0.931   2.514  1.00  0.00           C  
HETATM   21  C20 UNL     1      -5.028   0.489   2.456  1.00  0.00           C  
HETATM   22  O2  UNL     1      -5.843   1.379   2.731  1.00  0.00           O  
HETATM   23  H1  UNL     1      -2.778   2.690   1.661  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.156   1.908   3.157  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.841   2.638   3.062  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.252   1.413   1.431  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.832  -1.030  -0.213  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.695   1.739   1.808  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.983   2.143   0.647  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.222   2.552   0.319  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.300  -1.052  -1.131  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.228   1.336  -0.565  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.383  -1.207  -2.129  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.923   2.156  -1.156  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.538   1.314  -0.918  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.058   1.973  -2.485  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.510  -1.523  -3.239  1.00  0.00           H  
HETATM   38  H16 UNL     1       7.897  -1.016  -2.928  1.00  0.00           H  
HETATM   39  H17 UNL     1       7.617   0.690  -2.606  1.00  0.00           H  
HETATM   40  H18 UNL     1       6.880   0.764  -4.927  1.00  0.00           H  
HETATM   41  H19 UNL     1      -5.341  -0.242   0.182  1.00  0.00           H  
HETATM   42  H20 UNL     1      -4.166  -0.647  -1.074  1.00  0.00           H  
HETATM   43  H21 UNL     1      -5.239  -1.950  -0.330  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.360  -3.382   0.594  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.529  -2.347  -0.620  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.823  -2.536   1.034  1.00  0.00           H  
HETATM   47  H25 UNL     1      -3.605  -1.992   2.956  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.737  -2.815   1.829  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.788  -1.189   3.543  1.00  0.00           H  
HETATM   50  H28 UNL     1      -6.303  -1.056   1.799  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   21
CONECT    3    4   16
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    8    8
CONECT    7   28   29   30
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   13   13
CONECT   12   34   35   36
CONECT   13   14   37
CONECT   14   15   38   39
CONECT   15   40
CONECT   16   17   18   19
CONECT   17   41   42   43
CONECT   18   44   45   46
CONECT   19   20   47   48
CONECT   20   21   49   50
CONECT   21   22   22
END

HMDB0012329
     RDKit          3D
4-Oxoretinol
 50 50  0  0  0  0  0  0  0  0999 V2000
   -3.0471    2.0670    2.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6749    0.7753    2.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9186   -0.0496    1.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871    0.4317    1.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557   -0.1150    0.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    0.4936    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574    1.7847    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5719   -0.0838   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9017    0.3962   -0.9756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596   -0.2482   -1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022    0.1763   -2.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    1.4349   -1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8661   -0.5770   -2.8400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.1434   -3.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3361   -0.0096   -4.5618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708   -1.2878    0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -1.0436   -0.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7331   -2.4331    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310   -1.8370    2.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727   -0.9307    2.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277    0.4887    2.4559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8428    1.3786    2.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783    2.6903    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1557    1.9081    3.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8408    2.6376    3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    1.4128    1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324   -1.0300   -0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6945    1.7391    1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832    2.1434    0.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225    2.5522    0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3003   -1.0525   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    1.3360   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3829   -1.2072   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9230    2.1561   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5378    1.3136   -0.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0579    1.9725   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5101   -1.5228   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8966   -1.0155   -2.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6168    0.6904   -2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8800    0.7639   -4.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3411   -0.2420    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1658   -0.6474   -1.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2391   -1.9501   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -3.3819    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290   -2.3470   -0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -2.5361    1.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052   -1.9919    2.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7367   -2.8150    1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7879   -1.1892    3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3027   -1.0555    1.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Ketoretinol	ChEBI
4-oxo-ROL	ChEBI
3,7-Dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol	HMDB
4-Ketovitamin a(1)	HMDB
4-Ketovitamin-a-alcohol	HMDB
4-Ketovitamin-alpha-alcohol	HMDB
4-oxo-Retinol	HMDB
4-OxoROL	HMDB
4-Oxovitamin a1	HMDB
4-Oxovitamin-a-alcohol	HMDB
4-Oxovitamin-alpha-alcohol	HMDB
4OVA1	HMDB
all-trans-4-Oxoretinol	HMDB, ChEBI
OXR	HMDB

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.4351

Monoisotopic Molecular Weight

300.20893014

IUPAC Name

3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

Traditional Name

4-oxoretinol

CAS Registry Number

62702-55-0

SMILES

C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+

InChI Key

PLIUCYCUYQIBDZ-RMWYGNQTSA-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

Retinoid skeleton
Diterpenoid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:44597 )
Retinoids (C16683 )

Ontology

Not Available

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	0.012 g/L	ALOGPS
logP	5.31	ALOGPS
logP	4.03	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	16.44	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.62 m³·mol⁻¹	ChemAxon
Polarizability	36.69 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	187.798	30932474
DeepCCS	[M-H]-	185.134	30932474
DeepCCS	[M-2H]-	219.732	30932474
DeepCCS	[M+Na]+	194.959	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.6	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.5	32859911
AllCCS	[M-H]-	181.1	32859911
AllCCS	[M+Na-2H]-	181.8	32859911
AllCCS	[M+HCOO]-	182.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.55 minutes	32390414
Predicted by Siyang on May 30, 2022	20.3544 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3137.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	570.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	223.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	312.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	780.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	718.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1790.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	641.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1414.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	641.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	311.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	566.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Oxoretinol	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C	3684.1	Standard polar	33892256
4-Oxoretinol	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C	2644.0	Standard non polar	33892256
4-Oxoretinol	C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C	2721.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Oxoretinol,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CCC1=O	2742.7	Semi standard non polar	33892256
4-Oxoretinol,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C	2706.6	Semi standard non polar	33892256
4-Oxoretinol,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2771.7	Semi standard non polar	33892256
4-Oxoretinol,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2563.6	Standard non polar	33892256
4-Oxoretinol,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2709.7	Standard polar	33892256
4-Oxoretinol,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	2937.6	Semi standard non polar	33892256
4-Oxoretinol,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	2917.7	Semi standard non polar	33892256
4-Oxoretinol,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	3219.4	Semi standard non polar	33892256
4-Oxoretinol,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	2956.5	Standard non polar	33892256
4-Oxoretinol,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	2911.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1290000000-4649d7f3ab4f61c01faf	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-2129000000-ba7d9fd4931eaf6b6927	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinol 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 - 4-Oxoretinol 10V, Positive-QTOF	splash10-0f89-0593000000-fac47a7263b1f70432a3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOF	splash10-0f7k-2960000000-e6ecb0d2ae19b738762b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOF	splash10-1000-8920000000-f526453f90130e118ba0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOF	splash10-0002-0090000000-c06dba726fc1a33b336f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOF	splash10-014j-0090000000-13c1ec01c1d802584537	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOF	splash10-0frx-3490000000-ca40eaf3790e425d4408	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOF	splash10-014i-0090000000-d04e40563394d4c84f5d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOF	splash10-066s-0190000000-f4b17a8c6d2a8521525a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOF	splash10-0udi-0590000000-35e8dfa966822e3e2574	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Positive-QTOF	splash10-0fsr-0792000000-1526d46586ab5fe6ae7d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOF	splash10-00lb-1930000000-c9e30f5fc51a908c8495	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOF	splash10-002f-3900000000-eefd04e3e622ffcc6615	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02699

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028948

KNApSAcK ID

Not Available

Chemspider ID

4451124

KEGG Compound ID

C16683

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5289090

PDB ID

OXR

ChEBI ID

44597

Food Biomarker Ontology

Not Available

VMH ID

M01032

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ross SA, De Luca LM: A new metabolite of retinol: all-trans-4-oxo-retinol as a receptor activator and differentiation agent. Nutr Rev. 1996 Nov;54(11 Pt 1):355-6. [PubMed:9110564 ]
Faria TN, Rivi R, Derguini F, Pandolfi PP, Gudas LJ: 4-Oxoretinol, a metabolite of retinol in the human promyelocytic leukemia cell line NB4, induces cell growth arrest and granulocytic differentiation. Cancer Res. 1998 May 1;58(9):2007-13. [PubMed:9581846 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-Oxoretinol (HMDB0012329)

MOL for HMDB0012329 (4-Oxoretinol)

3D MOL for HMDB0012329 (4-Oxoretinol)

3D SDF for HMDB0012329 (4-Oxoretinol)

3D-SDF for HMDB0012329 (4-Oxoretinol)

PDB for HMDB0012329 (4-Oxoretinol)

3D PDB for HMDB0012329 (4-Oxoretinol)

SMILES for HMDB0012329 (4-Oxoretinol)

INCHI for HMDB0012329 (4-Oxoretinol)

Structure for HMDB0012329 (4-Oxoretinol)

3D Structure for HMDB0012329 (4-Oxoretinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra