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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 21:24:24 UTC

Update Date

2020-02-26 21:26:19 UTC

HMDB ID

HMDB0006285

Secondary Accession Numbers

HMDB06285

Metabolite Identification

Common Name

4-oxo-Retinoic acid

Description

4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203 , 7893159 , 17330217 , 16778795 , 17460545 ).

Structure

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

HMDB0006285
     RDKit          3D
4-oxo-Retinoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -2.5414    0.4341    2.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    0.5868    1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    0.5110    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.2723    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    0.1489   -0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -0.0910   -0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -0.0916    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6152   -0.2412   -1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -0.4790   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -0.6960   -1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -0.9214   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -1.0439    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832   -1.1083   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6087   -1.3341   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6815   -1.3801    1.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632   -1.5418   -0.8576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009    0.7264   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2882    0.5499   -2.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904    2.1258   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -0.3083   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.0761    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.7976    1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2452    1.5939    2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    1.2354    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -0.5732    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    0.5243    3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    0.1585    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    0.2261   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5999    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.3059    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -1.0940    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -0.1250   -2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -1.3124   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106   -0.3964   -2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -1.3285    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2918   -0.1119    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -1.9443    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.0799   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3855   -0.6974   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629   -0.4894   -2.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.3314   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2886    0.6041   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960    2.6176    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.1222   -0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0507    2.7630   -1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3552   -1.2788   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.3992   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058   -0.8894    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.6453    0.3983 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
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
M  END


  Mrv0541 02231220362D          

 23 23  0  0  0  0            999 V2000
   18.2035  -11.2696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3470   -3.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9180   -3.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0601  -10.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0601  -10.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745   -9.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745  -11.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6475   -9.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2350  -10.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4891  -10.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4891  -10.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745   -8.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2035   -9.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4891   -8.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4891   -7.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2035   -7.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2035   -6.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9180   -5.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9180   -5.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2035   -4.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6325   -4.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6325   -3.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 23  1  0  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  2  0  0  0  0
  6 12  1  0  0  0  0
  7 11  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006285

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

> <INCHI_KEY>
GGCUJPCCTQNTJF-FRCNGJHJSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.4186

> <EXACT_MASS>
314.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.618376317410906

> <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-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
4.347084349666667

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.890319822937116

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9966477450750295

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7513938153020066

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
98.484

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-oxo-retinoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006285
     RDKit          3D
4-oxo-Retinoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -2.5414    0.4341    2.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    0.5868    1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    0.5110    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.2723    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    0.1489   -0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -0.0910   -0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -0.0916    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6152   -0.2412   -1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -0.4790   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -0.6960   -1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -0.9214   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -1.0439    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832   -1.1083   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6087   -1.3341   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6815   -1.3801    1.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632   -1.5418   -0.8576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009    0.7264   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2882    0.5499   -2.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904    2.1258   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -0.3083   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.0761    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.7976    1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2452    1.5939    2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    1.2354    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -0.5732    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    0.5243    3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    0.1585    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    0.2261   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5999    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.3059    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -1.0940    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -0.1250   -2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -1.3124   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106   -0.3964   -2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -1.3285    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2918   -0.1119    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -1.9443    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.0799   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3855   -0.6974   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629   -0.4894   -2.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.3314   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2886    0.6041   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960    2.6176    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.1222   -0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0507    2.7630   -1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3552   -1.2788   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.3992   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058   -0.8894    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.6453    0.3983 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
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  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      33.980 -21.037   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.981  -6.406   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.314  -6.406   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      29.979 -18.727   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.979 -20.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.312 -17.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.312 -21.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.209 -17.393   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.439 -18.727   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.646 -18.727   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.646 -20.267   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.312 -16.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.980 -17.957   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.646 -15.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.646 -14.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.312 -13.336   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.980 -13.336   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.980 -11.796   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.314 -11.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.314  -9.486   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.980  -8.716   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.647  -8.716   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.647  -7.176   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4    5    6    8    9                                             
CONECT    5    4    7                                                       
CONECT    6    4   10   12                                                  
CONECT    7    5   11                                                       
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    6   11   13                                                  
CONECT   11    1    7   10                                                  
CONECT   12    6   14                                                       
CONECT   13   10                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23    2    3   22                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0006285
HETATM    1  C1  UNL     1      -2.541   0.434   2.789  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.330   0.587   1.571  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.741   0.511   0.325  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.333   0.272   0.331  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.547   0.149  -0.701  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.866  -0.091  -0.455  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.500  -0.092   0.875  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.615  -0.241  -1.546  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.949  -0.479  -1.509  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.166  -0.696  -1.475  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.236  -0.921  -0.583  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.112  -1.044   0.887  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.483  -1.108  -1.052  1.00  0.00           C  
HETATM   14  C14 UNL     1       7.609  -1.334  -0.213  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.682  -1.380   1.023  1.00  0.00           O  
HETATM   16  O2  UNL     1       8.863  -1.542  -0.858  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.701   0.726  -0.740  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.288   0.550  -2.160  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.290   2.126  -0.529  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.839  -0.308  -0.535  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.668   0.076   0.659  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.764   0.798   1.606  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.245   1.594   2.444  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.743   1.235   2.767  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.060  -0.573   2.765  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.170   0.524   3.687  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.829   0.158   1.313  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.938   0.226  -1.686  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.953   0.600   1.567  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.551   0.306   0.773  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.520  -1.094   1.304  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.039  -0.125  -2.510  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.910  -1.312  -2.678  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.511  -0.396  -2.576  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.029  -1.328   1.057  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.292  -0.112   1.394  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.627  -1.944   1.302  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.603  -1.080  -2.136  1.00  0.00           H  
HETATM   39  H16 UNL     1       9.385  -0.697  -1.028  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.963  -0.489  -2.326  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.655   1.331  -2.588  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.289   0.604  -2.743  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.796   2.618   0.323  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.368   2.122  -0.360  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.051   2.763  -1.418  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.355  -1.279  -0.337  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.429  -0.399  -1.469  1.00  0.00           H  
HETATM   48  H25 UNL     1      -6.006  -0.889   1.144  1.00  0.00           H  
HETATM   49  H26 UNL     1      -6.563   0.645   0.398  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   22
CONECT    3    4   17
CONECT    4    5    5   27
CONECT    5    6   28
CONECT    6    7    8    8
CONECT    7   29   30   31
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   13   13
CONECT   12   35   36   37
CONECT   13   14   38
CONECT   14   15   15   16
CONECT   16   39
CONECT   17   18   19   20
CONECT   18   40   41   42
CONECT   19   43   44   45
CONECT   20   21   46   47
CONECT   21   22   48   49
CONECT   22   23   23
END

HMDB0006285
     RDKit          3D
4-oxo-Retinoic acid
 49 49  0  0  0  0  0  0  0  0999 V2000
   -2.5414    0.4341    2.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    0.5868    1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    0.5110    0.3249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.2723    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469    0.1489   -0.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662   -0.0910   -0.4552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4999   -0.0916    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6152   -0.2412   -1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9494   -0.4790   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -0.6960   -1.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -0.9214   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120   -1.0439    0.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832   -1.1083   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6087   -1.3341   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6815   -1.3801    1.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632   -1.5418   -0.8576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009    0.7264   -0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2882    0.5499   -2.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2904    2.1258   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8392   -0.3083   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6685    0.0761    0.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7636    0.7976    1.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2452    1.5939    2.4436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7428    1.2354    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0604   -0.5732    2.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    0.5243    3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    0.1585    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383    0.2261   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5999    1.5674 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.3059    0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197   -1.0940    1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -0.1250   -2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9104   -1.3124   -2.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5106   -0.3964   -2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -1.3285    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2918   -0.1119    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274   -1.9443    1.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -1.0799   -2.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3855   -0.6974   -1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9629   -0.4894   -2.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.3314   -2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2886    0.6041   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960    2.6176    0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3679    2.1222   -0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0507    2.7630   -1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3552   -1.2788   -0.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4288   -0.3992   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0058   -0.8894    1.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5630    0.6453    0.3983 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
 14 16  1  0
  3 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-oxo-all-trans-Retinoic acid	ChEBI
4-oxo-AtRA	ChEBI
4-oxo-all-trans-Retinoate	Generator
4-oxo-Retinoate	Generator
4-keto-Retinoate	HMDB
4-keto-Retinoic acid	HMDB
4-Ketoretinoate	HMDB
4-Ketoretinoic acid	HMDB, MeSH
4-Oxoretinoate	HMDB
4-Oxoretinoic acid	HMDB, MeSH
4-Oxotretinoin	HMDB
all-trans-4-Oxoretinoate	HMDB
all-trans-4-Oxoretinoic acid	HMDB
ro 11-4824	HMDB
ro 12-4824	HMDB
4-oxo-13-cis-Retinoic acid	MeSH, HMDB
4-oxo-Isotretinoin	MeSH, HMDB
4-oxo-trans-Retinoic acid	MeSH, HMDB
4-Oxoretinoic acid, (13-cis)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

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

Traditional Name

4-oxo-retinoic acid

CAS Registry Number

38030-57-8

SMILES

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

InChI Identifier

InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

InChI Key

GGCUJPCCTQNTJF-FRCNGJHJSA-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
Cyclohexenone
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:80656 )
Retinoids (C16678 )
Retinoids (LMPR01090026 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006285)

Cellular substructure

Organelle

Nucleus (HMDB: HMDB0006285)

Organ

Liver (HMDB: HMDB0006285)
Kidney (HMDB: HMDB0006285)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006285)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006285)

Source

Endogenous

Endogenous (HMDB: HMDB0006285)

Animal

Animal (HMDB: HMDB0006285)

Exogenous

Food

Food (HMDB: HMDB0006285)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Role

Biological role

Energy source (HMDB: HMDB0006285)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006285)

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	0.0062 g/L	ALOGPS
logP	4.94	ALOGPS
logP	4.35	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.48 m³·mol⁻¹	ChemAxon
Polarizability	36.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	198.515	30932474
DeepCCS	[M-H]-	195.907	30932474
DeepCCS	[M-2H]-	230.449	30932474
DeepCCS	[M+Na]+	205.76	30932474
AllCCS	[M+H]+	179.5	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	182.4	32859911
AllCCS	[M+Na]+	183.2	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	183.0	32859911
AllCCS	[M+HCOO]-	183.7	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.	7.74 minutes	32390414
Predicted by Siyang on May 30, 2022	21.2837 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.77 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3186.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	608.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	232.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	347.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	184.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	833.4 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	805.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1816.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	667.3 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	1600.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	623.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	487.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	360.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	585.1 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	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-oxo-Retinoic acid	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	3922.4	Standard polar	33892256
4-oxo-Retinoic acid	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2642.5	Standard non polar	33892256
4-oxo-Retinoic acid	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2831.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-oxo-Retinoic acid,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CCC1=O	2814.9	Semi standard non polar	33892256
4-oxo-Retinoic acid,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CC=C1O[Si](C)(C)C	2843.8	Semi standard non polar	33892256
4-oxo-Retinoic acid,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2842.2	Semi standard non polar	33892256
4-oxo-Retinoic acid,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2579.6	Standard non polar	33892256
4-oxo-Retinoic acid,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	2840.1	Standard polar	33892256
4-oxo-Retinoic acid,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	3036.4	Semi standard non polar	33892256
4-oxo-Retinoic acid,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	3079.6	Semi standard non polar	33892256
4-oxo-Retinoic acid,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	3303.2	Semi standard non polar	33892256
4-oxo-Retinoic acid,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	2998.8	Standard non polar	33892256
4-oxo-Retinoic acid,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	3032.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-oxo-Retinoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1190000000-91cc9f2a067e55470ee6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-oxo-Retinoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-4149000000-1c6f86c22c6c874c8d5e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-oxo-Retinoic acid 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-oxo-Retinoic acid 10V, Positive-QTOF	splash10-014j-0393000000-ee02331a6bc33c74454c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 20V, Positive-QTOF	splash10-0pvs-1590000000-8302c918b8678930f190	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 40V, Positive-QTOF	splash10-05mk-6920000000-7c7f25147d9e24da29a6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 10V, Negative-QTOF	splash10-03xr-0069000000-d9c525084e53a73b4a7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 20V, Negative-QTOF	splash10-03xr-1096000000-f6a17be3ddcaa73ade82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 40V, Negative-QTOF	splash10-0f6w-4490000000-e09099a374036880e884	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 10V, Positive-QTOF	splash10-014i-0493000000-dc399cf44f47f04180bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 20V, Positive-QTOF	splash10-0f9b-1960000000-d3ac3e8652a2bc6d4a64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 40V, Positive-QTOF	splash10-0kbu-3910000000-9b786cbd709288245f36	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 10V, Negative-QTOF	splash10-03di-0079000000-16a7e691d9676e7c84c5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 20V, Negative-QTOF	splash10-014i-0390000000-afcececf071a831da85e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-oxo-Retinoic acid 40V, Negative-QTOF	splash10-016r-3920000000-80cd4fb181bfdfc81346	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Nucleus

Biospecimen Locations

Blood
Urine

Tissue Locations

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

FDB023877

KNApSAcK ID

Not Available

Chemspider ID

4941652

KEGG Compound ID

C16678

BioCyc ID

Not Available

BiGG ID

2430195

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437063

PDB ID

Not Available

ChEBI ID

80656

Food Biomarker Ontology

Not Available

VMH ID

CE2954

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Stahl W, Hanusch M, Sies H: 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8. [PubMed:8794203 ]
Hanusch M, Stahl W, Schulz WA, Sies H: Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Arch Biochem Biophys. 1995 Mar 10;317(2):423-8. [PubMed:7893159 ]
Gundersen TE, Bastani NE, Blomhoff R: Quantitative high-throughput determination of endogenous retinoids in human plasma using triple-stage liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1176-86. [PubMed:17330217 ]
Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. Epub 2006 Jun 15. [PubMed:16778795 ]
Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80. [PubMed:17460545 ]

Showing metabocard for 4-oxo-Retinoic acid (HMDB0006285)

MOL for HMDB0006285 (4-oxo-Retinoic acid)

3D MOL for HMDB0006285 (4-oxo-Retinoic acid)

3D SDF for HMDB0006285 (4-oxo-Retinoic acid)

3D-SDF for HMDB0006285 (4-oxo-Retinoic acid)

PDB for HMDB0006285 (4-oxo-Retinoic acid)

3D PDB for HMDB0006285 (4-oxo-Retinoic acid)

SMILES for HMDB0006285 (4-oxo-Retinoic acid)

INCHI for HMDB0006285 (4-oxo-Retinoic acid)

Structure for HMDB0006285 (4-oxo-Retinoic acid)

3D Structure for HMDB0006285 (4-oxo-Retinoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra