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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 19:40:54 UTC

Update Date

2021-09-14 15:47:52 UTC

HMDB ID

HMDB0006254

Secondary Accession Numbers

HMDB06254

Metabolite Identification

Common Name

4-Hydroxyretinoic acid

Description

4-Hydroxyretinoic acid belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Based on a literature review a significant number of articles have been published on 4-Hydroxyretinoic acid.

Structure

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

HMDB0006254
     RDKit          3D
4-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.3980   -2.6377   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.2520   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -0.3377    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -0.7682   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -0.0005    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9304   -0.4410   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.7920   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4200    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    0.0372    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3046    0.8346    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7049    0.4532    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8886   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679    1.3549    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0861    1.1194    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    2.0208    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5809   -0.1006   -0.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441    1.0424    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    1.3535    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727    2.0352   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025    1.2949    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5791    0.1415    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.0247   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7989   -0.6739   -1.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -2.5782   -1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7728   -3.0280    0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2557   -3.3159   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -1.7855   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.0241    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.2014    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.4717   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240   -1.6778   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    1.4271    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965   -0.9729   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.8527    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7986   -1.3992    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041   -1.5357   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -0.8394   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    2.3488    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1194   -0.2445   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    0.4484    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.2699    1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    1.4998    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5172    2.5644   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.7951    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.5906   -1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    1.7435   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188    2.0938    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6301    0.4468    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041   -0.1407    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8468   -1.8924    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6668   -0.2125   -1.1576 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  1  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
 22 50  1  0
 23 51  1  0
M  END


  Mrv0541 02231220352D          

 23 23  0  0  0  0            999 V2000
   18.1898  -11.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3333   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9042   -3.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0464  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0464  -10.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7608  -11.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7608   -9.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4754  -10.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4754  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2212  -10.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6337   -9.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7608   -8.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1898   -9.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4754   -8.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4754   -7.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7608   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1898   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1898   -6.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9042   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9042   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1898   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6187   -4.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6187   -3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  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  7  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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>
HMDB0006254

> <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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

> <INCHI_KEY>
KGUMXGDKXYTTEY-FRCNGJHJSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.3273712112017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.04

> <JCHEM_LOGP>
3.783556644

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.183567392005994

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.996647916720609

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4063077944597322

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
99.3063

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxyretinoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006254
     RDKit          3D
4-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.3980   -2.6377   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.2520   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -0.3377    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -0.7682   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -0.0005    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9304   -0.4410   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.7920   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4200    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    0.0372    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3046    0.8346    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7049    0.4532    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8886   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679    1.3549    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0861    1.1194    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    2.0208    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5809   -0.1006   -0.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441    1.0424    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    1.3535    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727    2.0352   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025    1.2949    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5791    0.1415    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.0247   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7989   -0.6739   -1.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -2.5782   -1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7728   -3.0280    0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2557   -3.3159   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -1.7855   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.0241    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.2014    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.4717   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240   -1.6778   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    1.4271    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965   -0.9729   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.8527    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7986   -1.3992    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041   -1.5357   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -0.8394   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    2.3488    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1194   -0.2445   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    0.4484    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.2699    1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    1.4998    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5172    2.5644   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.7951    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.5906   -1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    1.7435   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188    2.0938    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6301    0.4468    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041   -0.1407    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8468   -1.8924    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6668   -0.2125   -1.1576 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  1  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
 22 50  1  0
 23 51  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      33.954 -21.047   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.955  -6.417   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.288  -6.417   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      29.953 -18.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.953 -20.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.287 -21.047   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.287 -17.967   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.621 -20.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.621 -18.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.413 -18.737   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.183 -17.403   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.287 -16.427   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.954 -17.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.621 -15.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.621 -14.117   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.287 -13.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.954 -13.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.954 -11.807   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.288 -11.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.288  -9.497   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.954  -8.727   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.622  -8.727   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.622  -7.187   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4    5    7   10   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    8                                                       
CONECT    7    4    9   12                                                  
CONECT    8    1    6    9                                                  
CONECT    9    7    8   13                                                  
CONECT   10    4                                                            
CONECT   11    4                                                            
CONECT   12    7   14                                                       
CONECT   13    9                                                            
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    HMDB0006254
HETATM    1  C1  UNL     1      -3.398  -2.638  -0.585  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.853  -1.252  -0.161  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.931  -0.338   0.088  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.503  -0.768  -0.074  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.477  -0.000   0.136  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.930  -0.441  -0.030  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.332  -1.792  -0.445  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.914   0.420   0.208  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.304   0.037   0.060  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.305   0.835   0.279  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.705   0.453   0.131  1.00  0.00           C  
HETATM   12  C12 UNL     1       6.156  -0.889  -0.290  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.668   1.355   0.384  1.00  0.00           C  
HETATM   14  C14 UNL     1       8.086   1.119   0.280  1.00  0.00           C  
HETATM   15  O1  UNL     1       8.936   2.021   0.534  1.00  0.00           O  
HETATM   16  O2  UNL     1       8.581  -0.101  -0.101  1.00  0.00           O  
HETATM   17  C15 UNL     1      -3.244   1.042   0.490  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.650   1.353   1.879  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.673   2.035  -0.516  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.703   1.295   0.573  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.579   0.142   0.904  1.00  0.00           C  
HETATM   22  C20 UNL     1      -5.308  -1.025  -0.037  1.00  0.00           C  
HETATM   23  O3  UNL     1      -5.799  -0.674  -1.282  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.800  -2.578  -1.500  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.773  -3.028   0.243  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.256  -3.316  -0.683  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.295  -1.785  -0.389  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.646   1.024   0.459  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.002  -2.201   0.348  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.498  -2.472  -0.532  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.924  -1.678  -1.384  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.694   1.427   0.519  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.497  -0.973  -0.251  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.048   1.853   0.595  1.00  0.00           H  
HETATM   35  H12 UNL     1       6.799  -1.399   0.464  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.304  -1.536  -0.524  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.762  -0.839  -1.241  1.00  0.00           H  
HETATM   38  H15 UNL     1       6.281   2.349   0.695  1.00  0.00           H  
HETATM   39  H16 UNL     1       9.119  -0.245  -0.957  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.106   0.448   2.207  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.066   2.270   1.857  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.475   1.500   2.617  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.517   2.564  -1.046  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.108   2.795   0.042  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.059   1.591  -1.292  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.060   1.744  -0.396  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.919   2.094   1.322  1.00  0.00           H  
HETATM   48  H25 UNL     1      -6.630   0.447   0.707  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.504  -0.141   1.958  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.847  -1.892   0.379  1.00  0.00           H  
HETATM   51  H28 UNL     1      -6.667  -0.212  -1.158  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   50
CONECT   23   51
END

HMDB0006254
     RDKit          3D
4-Hydroxyretinoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
   -3.3980   -2.6377   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8525   -1.2520   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9311   -0.3377    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -0.7682   -0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771   -0.0005    0.1360 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9304   -0.4410   -0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.7920   -0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143    0.4200    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3044    0.0372    0.0603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3046    0.8346    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7049    0.4532    0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558   -0.8886   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679    1.3549    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0861    1.1194    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356    2.0208    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5809   -0.1006   -0.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2441    1.0424    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    1.3535    1.8788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727    2.0352   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7025    1.2949    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5791    0.1415    0.9045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078   -1.0247   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7989   -0.6739   -1.2822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -2.5782   -1.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7728   -3.0280    0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2557   -3.3159   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -1.7855   -0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6458    1.0241    0.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -2.2014    0.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.4717   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240   -1.6778   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6936    1.4271    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4965   -0.9729   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0477    1.8527    0.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7986   -1.3992    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041   -1.5357   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -0.8394   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2805    2.3488    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1194   -0.2445   -0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1061    0.4484    2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662    2.2699    1.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750    1.4998    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5172    2.5644   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1076    2.7951    0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.5906   -1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    1.7435   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9188    2.0938    1.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6301    0.4468    0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041   -0.1407    1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8468   -1.8924    0.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6668   -0.2125   -1.1576 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  1  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
 22 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acid	ChEBI
(7E,9E,11E,13E)-4-Hydroxyretinoic acid	ChEBI
4-Hydroxy-(7E,9E,11E,13E)-retinoic acid	ChEBI
4-Hydroxy-all-trans-retinoic acid	ChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate	Generator
(7E,9E,11E,13E)-4-Hydroxyretinoate	Generator
4-Hydroxy-(7E,9E,11E,13E)-retinoate	Generator
4-Hydroxy-all-trans-retinoate	Generator
4-Hydroxyretinoate	Generator
4-Hydroxy-13-cis-retinoate	HMDB
4-Hydroxy-13-cis-retinoic acid	HMDB, MeSH
4-Hydroxy-retinoate	HMDB
4-Hydroxy-retinoic acid	HMDB
4-OH-Retinoate	HMDB
4-OH-Retinoic acid	HMDB
all-trans-4-Hydroxyretinoate	HMDB
all-trans-4-Hydroxyretinoic acid	HMDB
rac-4-Hydroxy-all-trans-retinoate	HMDB
rac-4-Hydroxy-all-trans-retinoic acid	HMDB
4-Hydroxy-13-retinoic acid	MeSH, HMDB
4-Hydroxyretinoic acid, (13-cis)-isomer	MeSH, HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Traditional Name

4-hydroxyretinoic acid

CAS Registry Number

66592-72-1

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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+

InChI Key

KGUMXGDKXYTTEY-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
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoid (CHEBI:63795 )
Retinoids (C16677 )
Retinoids (LMPR01090025 )

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	0.009 g/L	ALOGPS
logP	5.04	ALOGPS
logP	3.78	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.31 m³·mol⁻¹	ChemAxon
Polarizability	37.33 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
DarkChem	[M+H]+	182.136	31661259
DarkChem	[M-H]-	180.908	31661259
DeepCCS	[M+H]+	199.986	30932474
DeepCCS	[M-H]-	197.249	30932474
DeepCCS	[M-2H]-	231.921	30932474
DeepCCS	[M+Na]+	207.446	30932474
AllCCS	[M+H]+	181.6	32859911
AllCCS	[M+H-H2O]+	178.5	32859911
AllCCS	[M+NH4]+	184.4	32859911
AllCCS	[M+Na]+	185.2	32859911
AllCCS	[M-H]-	183.9	32859911
AllCCS	[M+Na-2H]-	184.6	32859911
AllCCS	[M+HCOO]-	185.6	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.	7.27 minutes	32390414
Predicted by Siyang on May 30, 2022	19.3755 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.84 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3066.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	487.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	199.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	246.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	156.7 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	718.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1605.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	640.2 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	1599.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	560.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	456.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	264.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	498.9 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-Hydroxyretinoic acid	C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	4116.3	Standard polar	33892256
4-Hydroxyretinoic acid	C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2615.3	Standard non polar	33892256
4-Hydroxyretinoic acid	C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O	2730.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyretinoic acid,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1O[Si](C)(C)C	2807.1	Semi standard non polar	33892256
4-Hydroxyretinoic acid,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CCC1O	2841.2	Semi standard non polar	33892256
4-Hydroxyretinoic 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)CCC1O[Si](C)(C)C	2814.1	Semi standard non polar	33892256
4-Hydroxyretinoic acid,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1O[Si](C)(C)C(C)(C)C	3038.8	Semi standard non polar	33892256
4-Hydroxyretinoic acid,1TBDMS,isomer #2	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)CCC1O	3059.5	Semi standard non polar	33892256
4-Hydroxyretinoic 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)CCC1O[Si](C)(C)C(C)(C)C	3254.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k92-1093000000-7f88a5d83645fa2a79e9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0092-5008900000-f94c9a4b723e495dbc22	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyretinoic 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-Hydroxyretinoic acid 10V, Positive-QTOF	splash10-00kb-0292000000-4d5a6c9335a4fa5db05e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Positive-QTOF	splash10-0zg1-0590000000-0b50fabd74e810e935c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Positive-QTOF	splash10-0pba-3920000000-8958845f26cb19e0194b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Negative-QTOF	splash10-014i-0089000000-cdb17ed778c9480eb63e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Negative-QTOF	splash10-0gi1-0094000000-b75b3689212cfa9472cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Negative-QTOF	splash10-0a4i-4390000000-5614482c4d64bf67afaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Positive-QTOF	splash10-000t-0291000000-7a67cccc8b73d68d76e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Positive-QTOF	splash10-0f8i-0490000000-891d9992953ed919a7c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Positive-QTOF	splash10-000l-5920000000-8f663f06367ea569c02e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Negative-QTOF	splash10-014i-0096000000-123a0c931fe8f0c0d401	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Negative-QTOF	splash10-0udi-0190000000-3eec1ef4274b19e5f537	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Negative-QTOF	splash10-016r-4910000000-9e73ac1032f900dd901d	2021-09-22	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

FDB023862

KNApSAcK ID

Not Available

Chemspider ID

4943093

KEGG Compound ID

C16677

BioCyc ID

Not Available

BiGG ID

2299866

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6438629

PDB ID

Not Available

ChEBI ID

63795

Food Biomarker Ontology

Not Available

VMH ID

CE2956

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Rosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701.

Material Safety Data Sheet (MSDS)

Not Available

General References

Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. [PubMed:1932598 ]
Roberts ES, Vaz AD, Coon MJ: Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol Pharmacol. 1992 Feb;41(2):427-33. [PubMed:1538719 ]
Spear PA, Garcin H, Narbonne JF: Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. Can J Physiol Pharmacol. 1988 Sep;66(9):1181-6. [PubMed:2851384 ]

Showing metabocard for 4-Hydroxyretinoic acid (HMDB0006254)

MOL for HMDB0006254 (4-Hydroxyretinoic acid)

3D MOL for HMDB0006254 (4-Hydroxyretinoic acid)

3D SDF for HMDB0006254 (4-Hydroxyretinoic acid)

3D-SDF for HMDB0006254 (4-Hydroxyretinoic acid)

PDB for HMDB0006254 (4-Hydroxyretinoic acid)

3D PDB for HMDB0006254 (4-Hydroxyretinoic acid)

SMILES for HMDB0006254 (4-Hydroxyretinoic acid)

INCHI for HMDB0006254 (4-Hydroxyretinoic acid)

Structure for HMDB0006254 (4-Hydroxyretinoic acid)

3D Structure for HMDB0006254 (4-Hydroxyretinoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra