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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-06-18 12:13:05 UTC

Update Date

2021-09-14 15:46:22 UTC

HMDB ID

HMDB0012451

Secondary Accession Numbers

HMDB0060093
HMDB12451
HMDB60093

Metabolite Identification

Common Name

all-trans-5,6-Epoxyretinoic acid

Description

all-trans-5,6-Epoxyretinoic acid, also known as 5,6-epoxy-atRA, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-5,6-Epoxyretinoic acid is considered to be a practically insoluble (in water) and a weak acidic compound. all-trans-5,6-Epoxyretinoic acid is an isoprenoid lipid molecule. all-trans-5,6-Epoxyretinoic acid can be found primarily in human kidney and liver tissues; and in blood and urine. Within a cell, all-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm, in the extracellular space, or near the membrane.

Structure

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

HMDB0012451
     RDKit          3D
all-trans-5,6-Epoxyretinoic acid
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.9262   -0.4409   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420   -0.0220    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.2780   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1372    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904   -0.3912   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -1.6575   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2701    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -1.9383    1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.0816    0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -0.4293   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5806    0.2421   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    0.7935   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0447    1.6921    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    1.5935   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8860    0.2114    1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.2397    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.2702    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.0668    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -0.3238   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8187    0.2547    0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0191    0.0655   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0966   -0.2969   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838    0.2984    0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3155   -1.2935   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.5202   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.6238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -0.5853   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.1714    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772   -2.8383    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -2.1784    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3871   -1.1863    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659   -0.5634    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6168   -2.1138    0.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4211    0.3374   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1840   -1.1505   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313    1.1044   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1197   -0.4837   -2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    1.2978    1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    1.7838    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    2.7476    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    2.1761   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391    2.3327   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    0.9114   -2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.4809    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    1.4340    1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669    0.2933    2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1178    0.4275   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.3717   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -1.3105   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    0.5743    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3171    0.3640    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  7  5  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END


  Mrv1652307091917132D          

 23 24  0  0  0  0            999 V2000
    7.8815  -10.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0444  -10.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7875  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5017  -11.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2163  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9307  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6451  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3596  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0739  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7884  -11.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5028  -11.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2171  -11.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0739  -10.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2163  -10.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5028  -10.4358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3714  -13.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8838  -12.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585  -11.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6442  -12.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3585  -12.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731  -12.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0731  -11.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  5  1  0  0  0  0
 15 11  2  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 18  1  0  0  0  0
  1 18  1  0  0  0  0
 22 17  1  0  0  0  0
 22 16  1  0  0  0  0
  2 23  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012451

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

> <INCHI_KEY>
KEEHJLBAOLGBJZ-WEDZBJJJSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.4345

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.19479182962852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
4.540570249333333

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.936687619832732

> <JCHEM_PKA_STRONGEST_BASIC>
-4.282240537384268

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
96.5225

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012451
     RDKit          3D
all-trans-5,6-Epoxyretinoic acid
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.9262   -0.4409   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420   -0.0220    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.2780   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1372    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904   -0.3912   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -1.6575   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2701    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -1.9383    1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.0816    0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -0.4293   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5806    0.2421   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    0.7935   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0447    1.6921    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    1.5935   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8860    0.2114    1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.2397    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.2702    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.0668    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -0.3238   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8187    0.2547    0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0191    0.0655   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0966   -0.2969   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838    0.2984    0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3155   -1.2935   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.5202   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.6238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -0.5853   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.1714    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772   -2.8383    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -2.1784    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3871   -1.1863    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659   -0.5634    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6168   -2.1138    0.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4211    0.3374   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1840   -1.1505   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313    1.1044   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1197   -0.4837   -2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    1.2978    1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    1.7838    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    2.7476    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    2.1761   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391    2.3327   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    0.9114   -2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.4809    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    1.4340    1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669    0.2933    2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1178    0.4275   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.3717   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -1.3105   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    0.5743    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3171    0.3640    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  7  5  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END

HEADER    PROTEIN                                 09-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-19         0                                  
HETATM    1  C   UNK     0      14.712 -19.926   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.883 -20.371   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      18.270 -21.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.603 -21.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.937 -21.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      22.271 -21.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.604 -21.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.938 -21.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.271 -21.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.605 -21.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.939 -21.020   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      30.272 -21.790   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      26.271 -19.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.937 -19.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      28.939 -19.480   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.493 -24.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.450 -23.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.603 -21.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.269 -21.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.269 -23.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.603 -24.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.936 -23.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.936 -21.790   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   18   23                                                       
CONECT    3    4   23                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    5                                                            
CONECT   15   11                                                            
CONECT   16   22                                                            
CONECT   17   22                                                            
CONECT   18   19   23    2    1                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   17   16                                             
CONECT   23   18   22    2    3                                             
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0012451
HETATM    1  C1  UNL     1       1.926  -0.441  -0.910  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.842  -0.022   0.550  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.303  -0.278  -0.134  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.499  -0.137   0.536  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.790  -0.391  -0.111  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.034  -1.657  -0.652  1.00  0.00           O  
HETATM    7  C6  UNL     1      -3.691  -1.270   0.507  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.256  -1.938   1.823  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.150  -1.082   0.413  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.642  -0.429  -0.835  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.581   0.242  -1.641  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.489   0.793  -0.783  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.045   1.692   0.294  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.530   1.593  -1.619  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.886   0.211   1.173  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.217   0.240   1.105  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.473   0.270   1.053  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.579   0.067   0.232  1.00  0.00           C  
HETATM   19  C18 UNL     1       5.558  -0.324  -1.207  1.00  0.00           C  
HETATM   20  C19 UNL     1       6.819   0.255   0.730  1.00  0.00           C  
HETATM   21  C20 UNL     1       8.019   0.065  -0.040  1.00  0.00           C  
HETATM   22  O2  UNL     1       8.097  -0.297  -1.235  1.00  0.00           O  
HETATM   23  O3  UNL     1       9.284   0.298   0.567  1.00  0.00           O  
HETATM   24  H1  UNL     1       2.315  -1.294  -0.446  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.332   0.520  -1.001  1.00  0.00           H  
HETATM   26  H3  UNL     1       1.099  -0.624  -1.549  1.00  0.00           H  
HETATM   27  H4  UNL     1      -0.447  -0.585  -1.134  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.381   0.171   1.564  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.877  -2.838   2.045  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.165  -2.178   1.757  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.387  -1.186   2.644  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.566  -0.563   1.320  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.617  -2.114   0.452  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.421   0.337  -0.560  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.184  -1.151  -1.492  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.031   1.104  -2.188  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.120  -0.484  -2.347  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.861   1.298   1.312  1.00  0.00           H  
HETATM   39  H16 UNL     1      -5.153   1.784   0.193  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.668   2.748   0.185  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.134   2.176  -2.342  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.939   2.333  -1.036  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.919   0.911  -2.214  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.449   0.481   2.294  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.327   1.434   1.889  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.767   0.293   2.197  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.118   0.427  -1.837  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.511  -0.372  -1.535  1.00  0.00           H  
HETATM   49  H26 UNL     1       6.015  -1.311  -1.348  1.00  0.00           H  
HETATM   50  H27 UNL     1       6.930   0.574   1.783  1.00  0.00           H  
HETATM   51  H28 UNL     1       9.317   0.364   1.576  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   15   15
CONECT    3    4    4   27
CONECT    4    5   28
CONECT    5    6    7   12
CONECT    6    7
CONECT    7    8    9
CONECT    8   29   30   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   14
CONECT   13   38   39   40
CONECT   14   41   42   43
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   46
CONECT   18   19   20   20
CONECT   19   47   48   49
CONECT   20   21   50
CONECT   21   22   22   23
CONECT   23   51
END

HMDB0012451
     RDKit          3D
all-trans-5,6-Epoxyretinoic acid
 51 52  0  0  0  0  0  0  0  0999 V2000
    1.9262   -0.4409   -0.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8420   -0.0220    0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033   -0.2780   -0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4993   -0.1372    0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7904   -0.3912   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0339   -1.6575   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6911   -1.2701    0.5065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564   -1.9383    1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1501   -1.0816    0.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6418   -0.4293   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5806    0.2421   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4887    0.7935   -0.7828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0447    1.6921    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297    1.5935   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8860    0.2114    1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.2397    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.2702    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5788    0.0668    0.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5578   -0.3238   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8187    0.2547    0.7305 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0191    0.0655   -0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0966   -0.2969   -1.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2838    0.2984    0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3155   -1.2935   -0.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323    0.5202   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.6238   -1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4467   -0.5853   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3807    0.1714    1.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8772   -2.8383    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -2.1784    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3871   -1.1863    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5659   -0.5634    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6168   -2.1138    0.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4211    0.3374   -0.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1840   -1.1505   -1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0313    1.1044   -2.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1197   -0.4837   -2.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613    1.2978    1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1527    1.7838    0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6679    2.7476    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    2.1761   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9391    2.3327   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186    0.9114   -2.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4486    0.4809    2.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274    1.4340    1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7669    0.2933    2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1178    0.4275   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -0.3717   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0147   -1.3105   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9302    0.5743    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3171    0.3640    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  2 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
  7  5  1  0
 12  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 23 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
all-trans-5,6-Epoxy-5,6-dihydroretinoic acid	ChEBI
all-trans-5,6-Epoxy-5,6-dihydroretinoate	Generator
all-trans-5,6-Epoxyretinoate	Generator
5,6-Epoxy-5,6-dihydro-retinoate	HMDB
5,6-Epoxy-5,6-dihydro-retinoic acid	HMDB
5,6-Epoxyretinoic acid, (13-cis)-isomer	MeSH, HMDB
5,6-Epoxyretinoic acid, sodium salt	MeSH, HMDB
5,6-Epoxyretinoic acid	MeSH, HMDB
5,6-Epoxy-5,6-dihydroretinoic acid	HMDB
5,6-Epoxy-atRA	HMDB
all-trans-5,6-Epoxyretinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₃

Average Molecular Weight

316.4345

Monoisotopic Molecular Weight

316.203844762

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid

CAS Registry Number

13100-69-1

SMILES

C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+

InChI Key

KEEHJLBAOLGBJZ-WEDZBJJJSA-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
Epoxy fatty acid
Heterocyclic fatty acid
Oxepane
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Oxacycle
Oxirane
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

retinoid (CHEBI:80658 )
Retinoids (C16680 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060093)

Process

Not Available

Role

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	0.0039 g/L	ALOGPS
logP	5.74	ALOGPS
logP	4.54	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.52 m³·mol⁻¹	ChemAxon
Polarizability	37.19 Å³	ChemAxon
Number of Rings	2	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]+	180.748	31661259
DarkChem	[M-H]-	178.535	31661259
DeepCCS	[M-2H]-	229.651	30932474
DeepCCS	[M+Na]+	204.878	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.0	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	185.6	32859911
AllCCS	[M+Na-2H]-	186.2	32859911
AllCCS	[M+HCOO]-	187.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
all-trans-5,6-Epoxyretinoic acid	C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O	3855.1	Standard polar	33892256
all-trans-5,6-Epoxyretinoic acid	C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O	2452.8	Standard non polar	33892256
all-trans-5,6-Epoxyretinoic acid	C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O	2591.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
all-trans-5,6-Epoxyretinoic acid,1TMS,isomer #1	CC(/C=C/C12OC1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C	2632.5	Semi standard non polar	33892256
all-trans-5,6-Epoxyretinoic acid,1TBDMS,isomer #1	CC(/C=C/C12OC1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C	2846.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-5,6-Epoxyretinoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-9174000000-06301725f04dbf9da5b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-5,6-Epoxyretinoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9126000000-aaab7da3a75ae7d0ac69	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - all-trans-5,6-Epoxyretinoic 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 - all-trans-5,6-Epoxyretinoic acid 10V, Positive-QTOF	splash10-066s-0394000000-5ab9d9f9a6f2942b53fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 20V, Positive-QTOF	splash10-0a4i-3490000000-ecf50862a1162e1b0ba8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 40V, Positive-QTOF	splash10-0a4i-9300000000-801580c3c0c49c76fd08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 10V, Negative-QTOF	splash10-014i-0179000000-815f6a20a086d254820b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 20V, Negative-QTOF	splash10-01b9-1195000000-c470ae42b6bb7613d063	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 40V, Negative-QTOF	splash10-05a9-6960000000-e311a77eab0f7eeff493	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 10V, Positive-QTOF	splash10-00rt-0192000000-861041c7dc974b088a42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 20V, Positive-QTOF	splash10-0540-0590000000-4f77ff24993914b2af45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 40V, Positive-QTOF	splash10-0gdu-7910000000-3b294bfc029780e1a389	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 10V, Negative-QTOF	splash10-01b9-0198000000-91d1b99148247a6bd981	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 20V, Negative-QTOF	splash10-00y0-0971000000-29094eb01d6c33d9ba2e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - all-trans-5,6-Epoxyretinoic acid 40V, Negative-QTOF	splash10-066r-2932000000-86038457c94d4ed88c27	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB029067

KNApSAcK ID

Not Available

Chemspider ID

4515523

KEGG Compound ID

C16680

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363137

PDB ID

Not Available

ChEBI ID

80658

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

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for all-trans-5,6-Epoxyretinoic acid (HMDB0012451)

MOL for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

3D MOL for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

3D SDF for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

3D-SDF for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

PDB for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

3D PDB for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

SMILES for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

INCHI for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

Structure for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

3D Structure for HMDB0012451 (all-trans-5,6-Epoxyretinoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra