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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:07:28 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012794

Secondary Accession Numbers

HMDB12794

Metabolite Identification

Common Name

4-Oxoretinal

Description

4-Oxoretinal is a predominant retinoids during morphogenesis in mouse skin in vivo. Topical 4-oxoretinal and 4-oxoretinol promoted significant epidermal hyperplasia and metaplasia in mouse tail. They induced a moderate response for epidermal inflammation, compared with retinal, whereas neither 4-oxoretinal nor 4-oxoretinol prevented menadione-induced epidermal lipid peroxidation, unlike retinal and retinol. As analyzed by quantitative PCR, 4-oxoretinal and 4-oxoretinol did not reproduce the significant increased expression of genes coding for keratin 4, amphiregulin, heparin-EGF and CYP26A1, that did induce retinal and retinol. However, both retinal and 4-oxoretinal significantly inhibited the lipopolysaccharide-induced maturation of human dendritic cells in vitro. As analyzed in vivo and in vitro, 4-oxoretinal and 4-oxoretinol were not converted into retinoic acid. We conclude that 4-oxoretinal and 4-oxoretinol exert a moderate direct retinoid-like activity in vivo, thus confirming previous in vitro studies in amphibians showing 4-oxometabolites of vitamin A as bioactive agents rather than inactive catabolites.

Structure

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

HMDB0012794
     RDKit          3D
4-Oxoretinal
 48 48  0  0  0  0  0  0  0  0999 V2000
   -2.6204    1.4530   -2.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694    0.7381   -1.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330    0.1478   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953    0.2534   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523   -0.2064    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421   -0.0078    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7586    1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108    0.1578   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    0.3638   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380   -0.1024    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889    0.1014    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679    0.8047   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052   -0.3478    1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9354   -0.2311    1.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669   -0.7132    2.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.6506    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -0.0460    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119   -2.1112    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -0.7025   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6412   -1.7046    0.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6491    0.4855   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9087    0.7906   -2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8945    0.7763   -3.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462    1.8604   -3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    2.2811   -2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565    0.7752   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -0.6919    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977   -0.9379    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -1.5542    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306    0.1144    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7711    0.8103   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.8732   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7962   -0.6156    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.0006   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.1809   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    1.7474   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.8630    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5345    0.2322    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380    0.8342    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500   -0.8131    2.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    0.1826    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -2.6053   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739   -2.2888    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -2.5758    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324    1.3733   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7154    0.3175   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177    1.7995   -2.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362    0.0728   -2.8028 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  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  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
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END

  Mrv1652303262014172D          

 22 22  0  0  0  0            999 V2000
   11.6199  -15.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -14.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -14.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2698  -15.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -16.0649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -13.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -13.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -12.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0324  -11.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8574  -11.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199  -11.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7950  -11.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825  -10.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7950   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6199   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825   -8.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575   -8.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1451   -9.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3201   -9.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575  -10.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8430  -10.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5575  -11.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012794

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+

> <INCHI_KEY>
ZORDCCAUKPDLPN-ZBSJWCJSSA-N

> <FORMULA>
C20H26O2

> <MOLECULAR_WEIGHT>
298.4192

> <EXACT_MASS>
298.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.762863124329385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
4.188468097333335

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.83826678218938

> <JCHEM_PKA_STRONGEST_BASIC>
-4.061166896614546

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
97.55859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0012794
     RDKit          3D
4-Oxoretinal
 48 48  0  0  0  0  0  0  0  0999 V2000
   -2.6204    1.4530   -2.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694    0.7381   -1.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330    0.1478   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953    0.2534   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523   -0.2064    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421   -0.0078    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7586    1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108    0.1578   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    0.3638   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380   -0.1024    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889    0.1014    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679    0.8047   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052   -0.3478    1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9354   -0.2311    1.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669   -0.7132    2.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.6506    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -0.0460    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119   -2.1112    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -0.7025   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6412   -1.7046    0.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6491    0.4855   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9087    0.7906   -2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8945    0.7763   -3.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462    1.8604   -3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    2.2811   -2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565    0.7752   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -0.6919    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977   -0.9379    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -1.5542    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306    0.1144    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7711    0.8103   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.8732   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7962   -0.6156    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.0006   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.1809   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    1.7474   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.8630    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5345    0.2322    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380    0.8342    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500   -0.8131    2.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    0.1826    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -2.6053   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739   -2.2888    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -2.5758    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324    1.3733   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7154    0.3175   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177    1.7995   -2.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362    0.0728   -2.8028 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  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  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
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0      21.690 -28.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.460 -27.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.000 -27.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.770 -28.654   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      24.000 -29.988   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      21.690 -25.986   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.460 -24.653   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.690 -23.319   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.460 -21.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.000 -21.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.690 -20.652   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.151 -20.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.381 -19.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.151 -17.984   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.690 -17.984   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.381 -16.651   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.841 -16.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.071 -17.984   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.531 -17.984   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.841 -19.318   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.507 -20.088   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.841 -20.858   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   13   18   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0012794
HETATM    1  C1  UNL     1      -2.620   1.453  -2.836  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.469   0.738  -1.839  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.833   0.148  -0.810  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.395   0.253  -0.747  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.552  -0.206   0.192  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.842  -0.008   0.081  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.190  -0.759   1.723  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.011   0.158  -0.011  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.409   0.364  -0.134  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.238  -0.102   0.825  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.689   0.101   0.711  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.268   0.805  -0.449  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.505  -0.348   1.651  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.935  -0.231   1.687  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.567  -0.713   2.672  1.00  0.00           O  
HETATM   16  C15 UNL     1      -3.559  -0.651   0.186  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.371  -0.046   1.560  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.112  -2.111   0.177  1.00  0.00           C  
HETATM   19  C18 UNL     1      -5.010  -0.703  -0.156  1.00  0.00           C  
HETATM   20  O2  UNL     1      -5.641  -1.705   0.047  1.00  0.00           O  
HETATM   21  C19 UNL     1      -5.649   0.485  -0.743  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.909   0.791  -2.048  1.00  0.00           C  
HETATM   23  H1  UNL     1      -1.894   0.776  -3.322  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.246   1.860  -3.631  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.131   2.281  -2.273  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.857   0.775  -1.566  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.038  -0.692   1.001  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.198  -0.938   2.007  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.734  -1.554   1.332  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.631   0.114   2.117  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.771   0.810  -1.233  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.945   0.873  -0.936  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.796  -0.616   1.653  1.00  0.00           H  
HETATM   34  H12 UNL     1       7.339   1.001  -0.332  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.191   0.181  -1.383  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.733   1.747  -0.712  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.982  -0.863   2.486  1.00  0.00           H  
HETATM   38  H16 UNL     1       8.534   0.232   0.948  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.738   0.834   1.577  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.950  -0.813   2.240  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.412   0.183   1.948  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.743  -2.605  -0.646  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.074  -2.289   0.002  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.501  -2.576   1.094  1.00  0.00           H  
HETATM   45  H23 UNL     1      -5.632   1.373  -0.073  1.00  0.00           H  
HETATM   46  H24 UNL     1      -6.715   0.317  -0.997  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.218   1.799  -2.370  1.00  0.00           H  
HETATM   48  H26 UNL     1      -5.236   0.073  -2.803  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   22
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   15   38
CONECT   16   17   18   19
CONECT   17   39   40   41
CONECT   18   42   43   44
CONECT   19   20   20   21
CONECT   21   22   45   46
CONECT   22   47   48
END

HMDB0012794
     RDKit          3D
4-Oxoretinal
 48 48  0  0  0  0  0  0  0  0999 V2000
   -2.6204    1.4530   -2.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694    0.7381   -1.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8330    0.1478   -0.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3953    0.2534   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5523   -0.2064    0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421   -0.0078    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.7586    1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0108    0.1578   -0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4095    0.3638   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380   -0.1024    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6889    0.1014    0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2679    0.8047   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5052   -0.3478    1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9354   -0.2311    1.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5669   -0.7132    2.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.6506    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3708   -0.0460    1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119   -2.1112    0.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -0.7025   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6412   -1.7046    0.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6491    0.4855   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9087    0.7906   -2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8945    0.7763   -3.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2462    1.8604   -3.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    2.2811   -2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565    0.7752   -1.5656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0382   -0.6919    1.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1977   -0.9379    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7340   -1.5542    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6306    0.1144    2.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7711    0.8103   -1.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.8732   -0.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7962   -0.6156    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3394    1.0006   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.1809   -1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327    1.7474   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9815   -0.8630    2.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5345    0.2322    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380    0.8342    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500   -0.8131    2.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4125    0.1826    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7430   -2.6053   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0739   -2.2888    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5014   -2.5758    1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324    1.3733   -0.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7154    0.3175   -0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177    1.7995   -2.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2362    0.0728   -2.8028 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  2  0
  3 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22  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
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-all-trans-2,4,6,8-nonatetraenal	HMDB
4-Ketoretinal	HMDB
4-oxo-all-trans-Retinal	HMDB
4OVA	HMDB

Chemical Formula

C₂₀H₂₆O₂

Average Molecular Weight

298.4192

Monoisotopic Molecular Weight

298.193280076

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

CAS Registry Number

33532-44-4

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O

InChI Identifier

InChI=1S/C20H26O2/c1-15(7-6-8-16(2)13-14-21)9-11-18-17(3)10-12-19(22)20(18,4)5/h6-9,11,13-14H,10,12H2,1-5H3/b8-6+,11-9+,15-7+,16-13+

InChI Key

ZORDCCAUKPDLPN-ZBSJWCJSSA-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
Cyclohexenone
Enal
Alpha,beta-unsaturated aldehyde
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012794)

Source

Endogenous

Endogenous (HMDB: HMDB0012794)

Animal

Animal (HMDB: HMDB0012794)

Exogenous

Food

Food (HMDB: HMDB0012794)

Exogenous (HMDB: HMDB0012794)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012794)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012794)

Lipid metabolism pathway (HMDB: HMDB0012794)

Cellular process

Cell signaling (HMDB: HMDB0012794)

Biochemical process

Lipid transport (HMDB: HMDB0012794)

Role

Biological role

Energy source (HMDB: HMDB0012794)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012794)

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	0.007 g/L	ALOGPS
logP	5.47	ALOGPS
logP	4.19	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.56 m³·mol⁻¹	ChemAxon
Polarizability	35.76 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
DarkChem	[M+H]+	176.422	31661259
DarkChem	[M-H]-	175.668	31661259
DeepCCS	[M+H]+	194.814	30932474
DeepCCS	[M-H]-	191.956	30932474
DeepCCS	[M-2H]-	226.749	30932474
DeepCCS	[M+Na]+	202.073	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	178.9	32859911
AllCCS	[M+Na]+	179.8	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Oxoretinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O	3431.7	Standard polar	33892256
4-Oxoretinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O	2601.8	Standard non polar	33892256
4-Oxoretinal	C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=O	2611.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Oxoretinal,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C)=CC1	2704.8	Semi standard non polar	33892256
4-Oxoretinal,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C)=CC1	2417.1	Standard non polar	33892256
4-Oxoretinal,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C)=CC1	2763.4	Standard polar	33892256
4-Oxoretinal,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CC1	2928.6	Semi standard non polar	33892256
4-Oxoretinal,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CC1	2636.2	Standard non polar	33892256
4-Oxoretinal,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=O)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CC1	2889.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinal GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-2390000000-ae80440018b7880e093d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxoretinal 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-Oxoretinal 10V, Positive-QTOF	splash10-0002-0490000000-a6823593099fbaed6c4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 20V, Positive-QTOF	splash10-0002-2960000000-3a4e5a096946e2cb9d53	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 40V, Positive-QTOF	splash10-0f92-7940000000-6d7cc7a2009a0f4145a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 10V, Negative-QTOF	splash10-0002-0090000000-31e800acd103df7baca2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 20V, Negative-QTOF	splash10-014j-0090000000-8bed0f51ae47dee8402f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 40V, Negative-QTOF	splash10-0gbc-5390000000-900d357ffb0b666f354e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 10V, Negative-QTOF	splash10-014j-0090000000-733fa43232ceb2888d4f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 20V, Negative-QTOF	splash10-014i-0190000000-3a1a823f6ec06c3927c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 40V, Negative-QTOF	splash10-0udi-1390000000-0d264f4d7434c6f8f7ea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 10V, Positive-QTOF	splash10-001a-0970000000-de4c95545bd13a24b1dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 20V, Positive-QTOF	splash10-0bu9-1980000000-12284bfbc8b14f433bf7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxoretinal 40V, Positive-QTOF	splash10-00n3-7910000000-7841e7f00250ad2177d4	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029176

KNApSAcK ID

Not Available

Chemspider ID

30776653

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481523

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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.

Enzymes

Enzyme Details

1. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

Showing metabocard for 4-Oxoretinal (HMDB0012794)

MOL for HMDB0012794 (4-Oxoretinal)

3D MOL for HMDB0012794 (4-Oxoretinal)

3D SDF for HMDB0012794 (4-Oxoretinal)

3D-SDF for HMDB0012794 (4-Oxoretinal)

PDB for HMDB0012794 (4-Oxoretinal)

3D PDB for HMDB0012794 (4-Oxoretinal)

SMILES for HMDB0012794 (4-Oxoretinal)

INCHI for HMDB0012794 (4-Oxoretinal)

Structure for HMDB0012794 (4-Oxoretinal)

3D Structure for HMDB0012794 (4-Oxoretinal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes