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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-09 20:56:15 UTC

Update Date

2021-09-14 15:46:00 UTC

HMDB ID

HMDB0060123

Secondary Accession Numbers

HMDB60123

Metabolite Identification

Common Name

rac-5,6-Epoxy-retinoyl-beta-D-glucuronide

Description

rac-5,6-Epoxy-retinoyl-beta-D-glucuronide belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. rac-5,6-Epoxy-retinoyl-beta-D-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv1652303102016592D          

 35 37  0  0  0  0            999 V2000
    0.1914    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    5.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    8.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   10.9381    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1914   10.9381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   10.2237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2211   10.2237    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0461   10.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    9.5092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1914    8.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   11.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   11.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   10.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    9.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   10.9381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    9.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  1  0  0  0  0
  9  6  2  0  0  0  0
 11  7  1  0  0  0  0
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 13 10  2  0  0  0  0
 15  1  1  0  0  0  0
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 17 14  1  0  0  0  0
 19 18  1  0  0  0  0
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 21 19  1  0  0  0  0
 21 22  1  1  0  0  0
 23 20  1  0  0  0  0
 24  3  1  0  0  0  0
 24  4  1  0  0  0  0
 24 11  1  0  0  0  0
 25  5  1  6  0  0  0
 25 12  1  0  0  0  0
 26 13  1  1  0  0  0
 26 24  1  0  0  0  0
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 31 22  2  0  0  0  0
 32 22  1  0  0  0  0
 33 17  1  0  0  0  0
 23 33  1  6  0  0  0
 34 21  1  0  0  0  0
 34 23  1  0  0  0  0
 35 25  1  0  0  0  0
 35 26  1  0  0  0  0
M  END

HMDB0060123
     RDKit          3D
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide
 71 73  0  0  0  0  0  0  0  0999 V2000
    1.9306    0.9480    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067    0.5466   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.5651   -1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7998    0.9682   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2038    1.2490    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4623    0.0961   -1.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019   -0.0015   -1.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0278    0.1944    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.6385   -1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7461   -0.7563   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4895   -1.2330   -2.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3833   -0.4107   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1887   -2.5622    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3286   -2.3277   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1734   -1.2587   -0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7494   -2.1188    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  5  4  1  6
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M  END


  Mrv1652303102016592D          

 35 37  0  0  0  0            999 V2000
    0.1914    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    6.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    5.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 25  1  0  0  0  0
 35 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060123

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-15(10-13-26-24(3,4)11-7-12-25(26,5)35-26)8-6-9-16(2)14-17(27)33-23-20(30)18(28)19(29)21(34-23)22(31)32/h6,8-10,13-14,18-21,23,28-30H,7,11-12H2,1-5H3,(H,31,32)/b9-6+,13-10+,15-8+,16-14+/t18-,19+,20-,21-,23-,25-,26-/m1/s1

> <INCHI_KEY>
BZPOQLONXBJGAZ-XSHYMXFSSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.5586

> <EXACT_MASS>
492.23593275

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.91647571379657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
2.826110027333333

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212250468844253

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3892099259499915

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869063371000665

> <JCHEM_POLAR_SURFACE_AREA>
146.05

> <JCHEM_REFRACTIVITY>
128.82109999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060123
     RDKit          3D
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide
 71 73  0  0  0  0  0  0  0  0999 V2000
    1.9306    0.9480    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067    0.5466   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.5651   -1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7998    0.9682   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2358    0.9879   -0.9569 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2953    0.8899   -2.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7488   -0.2295   -1.7388 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1558   -0.4190   -2.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2350   -1.3248   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179   -1.2713    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8303   -0.0438    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2038    1.2490    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2425    2.3010   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4783    1.8077    1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623    0.0961   -1.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019   -0.0015   -1.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767   -0.0863   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -0.1824   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278    0.1944    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.6385   -1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7461   -0.7563   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4895   -1.2330   -2.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3833   -0.4107   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7991   -0.6116   -0.0583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4436    0.6198    0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5586    0.5611    0.8026 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4942    1.6688    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5798    1.7806    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1407    2.5596   -0.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3280   -0.7223    0.7474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.8041   -1.0354   -0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4918   -1.9050    1.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7219   -3.0248    0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0540   -1.4665    1.1371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1887   -2.5622    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.7109    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    0.1024    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860    1.4775    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992    0.2310   -2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    1.3010    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0628   -0.6070   -3.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6098   -1.3687   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8266    0.4342   -2.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3286   -2.3277   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1734   -1.2587   -0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7494   -2.1188    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854   -1.5017    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8937   -0.1437    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0196    0.0092    1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2830    1.8671   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3216    3.1010    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9672    2.8530   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.7335    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9016    1.0521    1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2560    2.1495    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828   -0.1854   -2.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -0.4738   -2.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    0.3602    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958    0.5883    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -0.6597    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7076    1.0397    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284   -0.9149   -2.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028   -1.0983   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2105    0.6969    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7683    2.1387   -1.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1993   -0.5965    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9833   -2.0054   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7206   -2.1103    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8989   -3.1870   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8518   -0.8449    2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591   -2.2623    1.2217 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
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  1
  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
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  7  5  1  0
 34 24  1  0
 12  5  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 17 58  1  0
 19 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 24 63  1  6
 26 64  1  1
 29 65  1  0
 30 66  1  1
 31 67  1  0
 32 68  1  1
 33 69  1  0
 34 70  1  1
 35 71  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       0.357   7.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.357  12.416   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.991   5.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.011   5.030   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897   9.748   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   8.415   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  11.082   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   5.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  13.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.897   7.081   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.897  12.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.897  15.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.897  20.418   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.357  20.418   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  19.084   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.413  19.084   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.953  19.084   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.897  17.751   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.357  15.083   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667  21.752   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.413  21.752   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.207  19.084   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.723  17.751   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.723  20.418   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667  16.417   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.357  17.751   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6    8    9                                                       
CONECT    7   11   12                                                       
CONECT    8    6   15                                                       
CONECT    9    6   16                                                       
CONECT   10   13   15                                                       
CONECT   11    7   24                                                       
CONECT   12    7   25                                                       
CONECT   13   10   26                                                       
CONECT   14   16   17                                                       
CONECT   15    1    8   10                                                  
CONECT   16    2    9   14                                                  
CONECT   17   14   27   33                                                  
CONECT   18   19   20   28                                                  
CONECT   19   18   21   29                                                  
CONECT   20   18   23   30                                                  
CONECT   21   19   22   34                                                  
CONECT   22   21   31   32                                                  
CONECT   23   20   33   34                                                  
CONECT   24    3    4   11   26                                             
CONECT   25    5   12   26   35                                             
CONECT   26   13   24   25   35                                             
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   22                                                            
CONECT   32   22                                                            
CONECT   33   17   23                                                       
CONECT   34   21   23                                                       
CONECT   35   25   26                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0060123
HETATM    1  C1  UNL     1       1.931   0.948   0.485  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.407   0.547  -0.840  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.789   0.565  -1.267  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.800   0.968  -0.520  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.236   0.988  -0.957  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.295   0.890  -2.286  1.00  0.00           O  
HETATM    7  C6  UNL     1       6.749  -0.229  -1.739  1.00  0.00           C  
HETATM    8  C7  UNL     1       8.156  -0.419  -2.193  1.00  0.00           C  
HETATM    9  C8  UNL     1       6.235  -1.325  -0.937  1.00  0.00           C  
HETATM   10  C9  UNL     1       7.018  -1.271   0.377  1.00  0.00           C  
HETATM   11  C10 UNL     1       7.830  -0.044   0.556  1.00  0.00           C  
HETATM   12  C11 UNL     1       7.204   1.249   0.090  1.00  0.00           C  
HETATM   13  C12 UNL     1       8.243   2.301  -0.234  1.00  0.00           C  
HETATM   14  C13 UNL     1       6.478   1.808   1.331  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.462   0.096  -1.691  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.102  -0.002  -1.360  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.077  -0.086  -1.075  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.418  -0.182  -0.749  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.028   0.194   0.576  1.00  0.00           C  
HETATM   20  C19 UNL     1      -3.341  -0.638  -1.617  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.746  -0.756  -1.329  1.00  0.00           C  
HETATM   22  O2  UNL     1      -5.490  -1.233  -2.257  1.00  0.00           O  
HETATM   23  O3  UNL     1      -5.383  -0.411  -0.162  1.00  0.00           O  
HETATM   24  C21 UNL     1      -6.799  -0.612  -0.058  1.00  0.00           C  
HETATM   25  O4  UNL     1      -7.444   0.620   0.023  1.00  0.00           O  
HETATM   26  C22 UNL     1      -8.559   0.561   0.803  1.00  0.00           C  
HETATM   27  C23 UNL     1      -9.494   1.669   0.470  1.00  0.00           C  
HETATM   28  O5  UNL     1     -10.580   1.781   1.083  1.00  0.00           O  
HETATM   29  O6  UNL     1      -9.141   2.560  -0.518  1.00  0.00           O  
HETATM   30  C24 UNL     1      -9.328  -0.722   0.747  1.00  0.00           C  
HETATM   31  O7  UNL     1      -9.804  -1.035  -0.501  1.00  0.00           O  
HETATM   32  C25 UNL     1      -8.492  -1.905   1.240  1.00  0.00           C  
HETATM   33  O8  UNL     1      -8.722  -3.025   0.426  1.00  0.00           O  
HETATM   34  C26 UNL     1      -7.054  -1.467   1.137  1.00  0.00           C  
HETATM   35  O9  UNL     1      -6.189  -2.562   1.125  1.00  0.00           O  
HETATM   36  H1  UNL     1       1.114   1.711   0.308  1.00  0.00           H  
HETATM   37  H2  UNL     1       1.473   0.102   1.019  1.00  0.00           H  
HETATM   38  H3  UNL     1       2.686   1.477   1.107  1.00  0.00           H  
HETATM   39  H4  UNL     1       4.099   0.231  -2.274  1.00  0.00           H  
HETATM   40  H5  UNL     1       4.514   1.301   0.473  1.00  0.00           H  
HETATM   41  H6  UNL     1       8.063  -0.607  -3.315  1.00  0.00           H  
HETATM   42  H7  UNL     1       8.610  -1.369  -1.843  1.00  0.00           H  
HETATM   43  H8  UNL     1       8.827   0.434  -2.129  1.00  0.00           H  
HETATM   44  H9  UNL     1       6.329  -2.328  -1.437  1.00  0.00           H  
HETATM   45  H10 UNL     1       5.173  -1.259  -0.647  1.00  0.00           H  
HETATM   46  H11 UNL     1       7.749  -2.119   0.291  1.00  0.00           H  
HETATM   47  H12 UNL     1       6.385  -1.502   1.259  1.00  0.00           H  
HETATM   48  H13 UNL     1       8.894  -0.144   0.182  1.00  0.00           H  
HETATM   49  H14 UNL     1       8.020   0.009   1.678  1.00  0.00           H  
HETATM   50  H15 UNL     1       9.283   1.867  -0.278  1.00  0.00           H  
HETATM   51  H16 UNL     1       8.322   3.101   0.541  1.00  0.00           H  
HETATM   52  H17 UNL     1       7.967   2.853  -1.159  1.00  0.00           H  
HETATM   53  H18 UNL     1       5.936   2.734   1.066  1.00  0.00           H  
HETATM   54  H19 UNL     1       5.902   1.052   1.858  1.00  0.00           H  
HETATM   55  H20 UNL     1       7.256   2.149   2.081  1.00  0.00           H  
HETATM   56  H21 UNL     1       1.883  -0.185  -2.667  1.00  0.00           H  
HETATM   57  H22 UNL     1      -0.233  -0.474  -2.616  1.00  0.00           H  
HETATM   58  H23 UNL     1      -0.700   0.360   0.197  1.00  0.00           H  
HETATM   59  H24 UNL     1      -2.196   0.588   1.221  1.00  0.00           H  
HETATM   60  H25 UNL     1      -3.473  -0.660   1.069  1.00  0.00           H  
HETATM   61  H26 UNL     1      -3.708   1.040   0.431  1.00  0.00           H  
HETATM   62  H27 UNL     1      -2.928  -0.915  -2.578  1.00  0.00           H  
HETATM   63  H28 UNL     1      -7.203  -1.098  -0.960  1.00  0.00           H  
HETATM   64  H29 UNL     1      -8.210   0.697   1.869  1.00  0.00           H  
HETATM   65  H30 UNL     1      -8.768   2.139  -1.385  1.00  0.00           H  
HETATM   66  H31 UNL     1     -10.199  -0.597   1.448  1.00  0.00           H  
HETATM   67  H32 UNL     1      -9.983  -2.005  -0.610  1.00  0.00           H  
HETATM   68  H33 UNL     1      -8.721  -2.110   2.288  1.00  0.00           H  
HETATM   69  H34 UNL     1      -7.899  -3.187  -0.102  1.00  0.00           H  
HETATM   70  H35 UNL     1      -6.852  -0.845   2.045  1.00  0.00           H  
HETATM   71  H36 UNL     1      -5.259  -2.262   1.222  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   15   15
CONECT    3    4    4   39
CONECT    4    5   40
CONECT    5    6    7   12
CONECT    6    7
CONECT    7    8    9
CONECT    8   41   42   43
CONECT    9   10   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   14
CONECT   13   50   51   52
CONECT   14   53   54   55
CONECT   15   16   56
CONECT   16   17   17   57
CONECT   17   18   58
CONECT   18   19   20   20
CONECT   19   59   60   61
CONECT   20   21   62
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   34   63
CONECT   25   26
CONECT   26   27   30   64
CONECT   27   28   28   29
CONECT   29   65
CONECT   30   31   32   66
CONECT   31   67
CONECT   32   33   34   68
CONECT   33   69
CONECT   34   35   70
CONECT   35   71
END

HMDB0060123
     RDKit          3D
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide
 71 73  0  0  0  0  0  0  0  0999 V2000
    1.9306    0.9480    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067    0.5466   -0.8395 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7891    0.5651   -1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7998    0.9682   -0.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2358    0.9879   -0.9569 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2953    0.8899   -2.2863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7488   -0.2295   -1.7388 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1558   -0.4190   -2.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2350   -1.3248   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0179   -1.2713    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8303   -0.0438    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2038    1.2490    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2425    2.3010   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4783    1.8077    1.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4623    0.0961   -1.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1019   -0.0015   -1.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767   -0.0863   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4185   -0.1824   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0278    0.1944    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3409   -0.6385   -1.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7461   -0.7563   -1.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4895   -1.2330   -2.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3833   -0.4107   -0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7991   -0.6116   -0.0583 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4436    0.6198    0.0231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5586    0.5611    0.8026 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.4942    1.6688    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5798    1.7806    1.0831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1407    2.5596   -0.5183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3280   -0.7223    0.7474 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.8041   -1.0354   -0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4918   -1.9050    1.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.7219   -3.0248    0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0540   -1.4665    1.1371 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1887   -2.5622    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1142    1.7109    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733    0.1024    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6860    1.4775    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0992    0.2310   -2.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5144    1.3010    0.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0628   -0.6070   -3.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6098   -1.3687   -1.8432 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8266    0.4342   -2.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3286   -2.3277   -1.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1734   -1.2587   -0.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7494   -2.1188    0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3854   -1.5017    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8937   -0.1437    0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0196    0.0092    1.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2830    1.8671   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3216    3.1010    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9672    2.8530   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    2.7335    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9016    1.0521    1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2560    2.1495    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8828   -0.1854   -2.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -0.4738   -2.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    0.3602    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1958    0.5883    1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725   -0.6597    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7076    1.0397    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284   -0.9149   -2.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028   -1.0983   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2105    0.6969    1.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7683    2.1387   -1.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1993   -0.5965    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9833   -2.0054   -0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7206   -2.1103    2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8989   -3.1870   -0.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8518   -0.8449    2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2591   -2.2623    1.2217 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
  5  4  1  6
  5  6  1  0
  6  7  1  0
  7  8  1  1
  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
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 26 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  7  5  1  0
 34 24  1  0
 12  5  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  3 39  1  0
  4 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  0
 16 57  1  0
 17 58  1  0
 19 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 24 63  1  6
 26 64  1  1
 29 65  1  0
 30 66  1  1
 31 67  1  0
 32 68  1  1
 33 69  1  0
 34 70  1  1
 35 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
rac-5,6-Epoxy-retinoyl-b-D-glucuronide	Generator
rac-5,6-Epoxy-retinoyl-β-D-glucuronide	Generator

Chemical Formula

C₂₆H₃₆O₉

Average Molecular Weight

492.5586

Monoisotopic Molecular Weight

492.23593275

IUPAC Name

(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2R,3S,4R,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-[(1R,6R)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C26H36O9/c1-15(10-13-26-24(3,4)11-7-12-25(26,5)35-26)8-6-9-16(2)14-17(27)33-23-20(30)18(28)19(29)21(34-23)22(31)32/h6,8-10,13-14,18-21,23,28-30H,7,11-12H2,1-5H3,(H,31,32)/b9-6+,13-10+,15-8+,16-14+/t18-,19+,20-,21-,23-,25-,26-/m1/s1

InChI Key

BZPOQLONXBJGAZ-XSHYMXFSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Retinoid ester
Diterpenoid
Retinoid skeleton
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Beta-hydroxy acid
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Acetal
Dialkyl ether
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Blood (HMDB: HMDB0060123)
Urine (HMDB: HMDB0060123)

Organ

Liver (HMDB: HMDB0060123)
Kidney (HMDB: HMDB0060123)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060123)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060123)

Cellular substructure

Membrane (HMDB: HMDB0060123)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0060123)

Source

Endogenous

Endogenous (HMDB: HMDB0060123)

Animal

Animal (HMDB: HMDB0060123)

Exogenous

Food

Food (HMDB: HMDB0060123)

Animal origin

Bovine

Swine

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

Poultry

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)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)

Venison

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

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Caprae

Domestic goat (FooDB: FOOD00529)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0060123)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0060123)

Cellular process

Cell signaling (HMDB: HMDB0060123)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0060123)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0060123)

Nutrient

Nutrient (HMDB: HMDB0060123)

Physical Properties

State

Not Available

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	0.046 g/L	ALOGPS
logP	3.14	ALOGPS
logP	2.83	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.82 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	254.346	30932474
DeepCCS	[M+Na]+	229.831	30932474
AllCCS	[M+H]+	221.4	32859911
AllCCS	[M+H-H2O]+	219.5	32859911
AllCCS	[M+NH4]+	223.2	32859911
AllCCS	[M+Na]+	223.7	32859911
AllCCS	[M-H]-	216.0	32859911
AllCCS	[M+Na-2H]-	218.1	32859911
AllCCS	[M+HCOO]-	220.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide	C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O	4994.5	Standard polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide	C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O	3695.5	Standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide	C\C(\C=C\[C@]12O[C@]1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O	3928.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O	3683.5	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O	3678.3	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	3694.9	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O	3666.7	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O	3610.7	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	3638.0	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	3645.0	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O	3610.8	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #5	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3639.2	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TMS,isomer #6	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C	3609.2	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	3584.2	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	3598.8	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3627.0	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3593.5	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,4TMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3587.4	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TBDMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	3904.1	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TBDMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3900.2	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TBDMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3922.0	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,1TBDMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O	3914.4	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	4076.0	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4074.5	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4087.8	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4065.5	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #5	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4078.8	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,2TBDMS,isomer #6	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4074.5	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TBDMS,isomer #1	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4231.4	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TBDMS,isomer #2	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4268.8	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TBDMS,isomer #3	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4252.1	Semi standard non polar	33892256
rac-5,6-Epoxy-retinoyl-beta-D-glucuronide,3TBDMS,isomer #4	CC(/C=C/[C@]12O[C@]1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)O[C@@H]1O[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4247.5	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 - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9331026000-87b46fb80419bba940ae	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 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 - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 10V, Positive-QTOF	splash10-00os-0795500000-21f272da50dc994a7a76	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 20V, Positive-QTOF	splash10-0a4i-2691000000-e1d7b91b687c7d8cef69	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 40V, Positive-QTOF	splash10-0a4i-7920000000-15d1cd354e47bac03aab	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 10V, Negative-QTOF	splash10-0002-1293400000-d7e0df32e87a79c39aa4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 20V, Negative-QTOF	splash10-01dj-4955200000-4de1039e1dcd195c095a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - rac-5,6-Epoxy-retinoyl-beta-D-glucuronide 40V, Negative-QTOF	splash10-00ke-9843000000-1c9692f81492891c5679	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

FDB034576

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769835

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 rac-5,6-Epoxy-retinoyl-beta-D-glucuronide (HMDB0060123)

MOL for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

3D MOL for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

3D SDF for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

3D-SDF for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

PDB for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

3D PDB for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

SMILES for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

INCHI for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

Structure for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

3D Structure for HMDB0060123 (rac-5,6-Epoxy-retinoyl-beta-D-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra