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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:07:22 UTC

Update Date

2022-03-07 02:51:27 UTC

HMDB ID

HMDB0012789

Secondary Accession Numbers

HMDB12789

Metabolite Identification

Common Name

4-Oxo-13-cis-retinoate

Description

4-oxo-9-cis retinoic acid (4-oxo-9cRA) is identified as a major plasma metabolite of 9-cis retinoic acid. Plasma levels of 4-oxo-9-cRA were initially 71% of those of 9cRA, but in contrast to 9cRA, there was no decline in plasma levels.Despite a decline in plasma levels of 9cRA over time, levels of the 4-oxo metabolite tended to persist. While the 4-oxo metabolite is less potent than the parent compound.

Structure

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

HMDB0012789
     RDKit          3D
4-Oxo-13-cis-retinoate
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.8805   -1.3953    1.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -0.0500    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    0.4679    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.3253    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    0.0137    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.7905    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589   -2.1330    0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.3410   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463   -1.1157   -0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463   -0.6475   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2215   -1.4652   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -2.8260   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315   -1.0784   -1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.1766   -2.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    1.0912   -2.6531 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7358    0.4616   -3.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670    1.7842    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6738    1.6998   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    2.6925    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    2.4421    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7628    3.1802   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    2.1643    1.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3085    0.6523    1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663   -1.4263    2.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708   -2.1671    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -1.6774    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241   -1.3169    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    0.9728   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.0441    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.4431    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.8854   -0.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6354   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.0800   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962    0.3275   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0635   -3.3745   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -2.7266    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3017   -3.3928   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2048   -1.7592   -1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4544    0.8823   -2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    2.0659   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    2.4070   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048    0.7001   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550    2.1503    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815    3.4915    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    3.1718   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9881    2.6846    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3441    2.3539    2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0096    0.4258    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7517    0.3657    2.4343 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  2  0
 20 22  1  0
 22 23  1  0
 23  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
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END


  Mrv0541 02251208092D          

 23 23  0  0  0  0            999 V2000
   11.4030  -12.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9906  -12.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4030  -11.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279  -11.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6404  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4654  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8778  -11.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8778  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7021  -10.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1146  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9395  -10.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3520  -11.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3526  -10.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9414   -9.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3563   -8.7066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1171   -9.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9906  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7051  -10.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9906  -10.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1656  -10.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531  -10.1338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531  -11.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1656  -12.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 23  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012789

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
YOFBBAJVETYSCH-IWRFDTMXSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.4186

> <EXACT_MASS>
314.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.57001801548519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
4.347084349666667

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.83826678221873

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.9966477449975715

> <JCHEM_PKA_STRONGEST_BASIC>
-7.559579122554959

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
98.48399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.60e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012789
     RDKit          3D
4-Oxo-13-cis-retinoate
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.8805   -1.3953    1.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -0.0500    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    0.4679    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.3253    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    0.0137    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.7905    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589   -2.1330    0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.3410   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463   -1.1157   -0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463   -0.6475   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2215   -1.4652   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -2.8260   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315   -1.0784   -1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.1766   -2.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    1.0912   -2.6531 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7358    0.4616   -3.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670    1.7842    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6738    1.6998   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    2.6925    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    2.4421    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7628    3.1802   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    2.1643    1.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3085    0.6523    1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663   -1.4263    2.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708   -2.1671    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -1.6774    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241   -1.3169    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    0.9728   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.0441    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.4431    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.8854   -0.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6354   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.0800   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962    0.3275   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0635   -3.3745   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -2.7266    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3017   -3.3928   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2048   -1.7592   -1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4544    0.8823   -2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    2.0659   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    2.4070   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048    0.7001   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550    2.1503    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815    3.4915    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    3.1718   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9881    2.6846    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3441    2.3539    2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0096    0.4258    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7517    0.3657    2.4343 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  2  0
 20 22  1  0
 22 23  1  0
 23  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
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      21.286 -24.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.516 -22.918   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.286 -21.584   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.825 -21.584   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.595 -20.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.135 -20.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.905 -21.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.905 -18.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.444 -18.916   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.214 -20.250   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.754 -20.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.524 -21.585   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.525 -18.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.757 -17.584   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      30.532 -16.252   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      28.219 -17.580   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.516 -20.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.850 -19.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.516 -18.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.976 -20.250   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.206 -18.916   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      18.206 -21.584   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.976 -22.918   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    3   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23    2   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

COMPND    HMDB0012789
HETATM    1  C1  UNL     1      -3.881  -1.395   1.947  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.013  -0.050   1.334  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.952   0.468   0.700  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.713  -0.325   0.647  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.602   0.014   0.088  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.624  -0.790   0.046  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.759  -2.133   0.654  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.720  -0.341  -0.562  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.946  -1.116  -0.620  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.046  -0.647  -1.238  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.221  -1.465  -1.257  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.189  -2.826  -0.584  1.00  0.00           C  
HETATM   13  C13 UNL     1       6.331  -1.078  -1.838  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.469   0.177  -2.497  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.656   1.091  -2.653  1.00  0.00           O  
HETATM   16  O2  UNL     1       7.736   0.462  -3.084  1.00  0.00           O  
HETATM   17  C15 UNL     1      -2.967   1.784   0.045  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.674   1.700  -1.445  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.966   2.693   0.714  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.304   2.442   0.244  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.763   3.180  -0.613  1.00  0.00           O  
HETATM   22  C19 UNL     1      -5.033   2.164   1.503  1.00  0.00           C  
HETATM   23  C20 UNL     1      -5.309   0.652   1.469  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.066  -1.426   2.709  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.671  -2.167   1.160  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.838  -1.677   2.415  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.724  -1.317   1.133  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.536   0.973  -0.397  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.634  -2.044   1.367  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.106  -2.443   1.221  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.101  -2.885  -0.094  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.678   0.635  -1.023  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.973  -2.080  -0.161  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.896   0.327  -1.660  1.00  0.00           H  
HETATM   35  H12 UNL     1       6.063  -3.375  -0.964  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.226  -2.727   0.498  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.302  -3.393  -0.961  1.00  0.00           H  
HETATM   38  H15 UNL     1       7.205  -1.759  -1.817  1.00  0.00           H  
HETATM   39  H16 UNL     1       8.454   0.882  -2.479  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.581   2.066  -1.985  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.877   2.407  -1.679  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.405   0.700  -1.776  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.355   2.150   1.474  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.481   3.492   1.330  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.321   3.172  -0.039  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.988   2.685   1.574  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.344   2.354   2.354  1.00  0.00           H  
HETATM   48  H25 UNL     1      -6.010   0.426   0.649  1.00  0.00           H  
HETATM   49  H26 UNL     1      -5.752   0.366   2.434  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   23
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   21   22
CONECT   22   23   46   47
CONECT   23   48   49
END

HMDB0012789
     RDKit          3D
4-Oxo-13-cis-retinoate
 49 49  0  0  0  0  0  0  0  0999 V2000
   -3.8805   -1.3953    1.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0128   -0.0500    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9523    0.4679    0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -0.3253    0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    0.0137    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6236   -0.7905    0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7589   -2.1330    0.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.3410   -0.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9463   -1.1157   -0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463   -0.6475   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2215   -1.4652   -1.2573 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1887   -2.8260   -0.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3315   -1.0784   -1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4691    0.1766   -2.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6565    1.0912   -2.6531 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7358    0.4616   -3.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9670    1.7842    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6738    1.6998   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9661    2.6925    0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038    2.4421    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7628    3.1802   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333    2.1643    1.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3085    0.6523    1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0663   -1.4263    2.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708   -2.1671    1.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -1.6774    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241   -1.3169    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    0.9728   -0.3966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.0441    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.4431    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011   -2.8854   -0.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6781    0.6354   -1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.0800   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8962    0.3275   -1.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0635   -3.3745   -0.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2264   -2.7266    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3017   -3.3928   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2048   -1.7592   -1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4544    0.8823   -2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    2.0659   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8774    2.4070   -1.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048    0.7001   -1.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550    2.1503    1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815    3.4915    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213    3.1718   -0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9881    2.6846    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3441    2.3539    2.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0096    0.4258    0.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7517    0.3657    2.4343 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  2  0
 20 22  1  0
 22 23  1  0
 23  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
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-oxo-13-cis-Retinoic acid	Generator
3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6Z,8Z)-nonatetraen-1-Oate	HMDB
3,7-Dimethyl-9-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-(2E,4Z,6Z,8Z)-nonatetraen-1-Oic acid	HMDB
4-keto-13-cis-Retinoate	HMDB
4-keto-13-cis-Retinoic acid	HMDB
4-oxo-13-cis-Retinoic acid anion	HMDB
4O13CVA	HMDB
(2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate	Generator

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

YOFBBAJVETYSCH-IWRFDTMXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Cyclohexenone
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0012789)
Cell membrane (HMDB: HMDB0012789)

Cellular substructure

Extracellular (HMDB: HMDB0012789)
Membrane (HMDB: HMDB0012789)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012789)

Source

Endogenous

Endogenous (HMDB: HMDB0012789)

Animal

Animal (HMDB: HMDB0012789)

Exogenous

Food

Food (HMDB: HMDB0012789)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0012789)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0012789)

Cellular process

Cell signaling (HMDB: HMDB0012789)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0012789)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0012789)

Nutrient

Nutrient (HMDB: HMDB0012789)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012789)

Emulsifier (HMDB: HMDB0012789)

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	0.0056 g/L	ALOGPS
logP	4.83	ALOGPS
logP	4.35	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
pKa (Strongest Basic)	-7.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.48 m³·mol⁻¹	ChemAxon
Polarizability	36.57 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]+	183.146	31661259
DarkChem	[M-H]-	182.289	31661259
DeepCCS	[M+H]+	198.645	30932474
DeepCCS	[M-H]-	196.116	30932474
DeepCCS	[M-2H]-	230.579	30932474
DeepCCS	[M+Na]+	206.332	30932474
AllCCS	[M+H]+	179.4	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	182.3	32859911
AllCCS	[M+Na]+	183.1	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	183.0	32859911
AllCCS	[M+HCOO]-	183.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Oxo-13-cis-retinoate	C\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=C/C(/C)=C\C(O)=O	4003.1	Standard polar	33892256
4-Oxo-13-cis-retinoate	C\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=C/C(/C)=C\C(O)=O	2619.1	Standard non polar	33892256
4-Oxo-13-cis-retinoate	C\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=C/C(/C)=C\C(O)=O	2768.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Oxo-13-cis-retinoate,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O[Si](C)(C)C)C(C)(C)C(=O)CC1	2825.3	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)C(O[Si](C)(C)C)=CC1	2819.7	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C)=CC1	2793.1	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C)=CC1	2570.1	Standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C)=CC1	2893.9	Standard polar	33892256
4-Oxo-13-cis-retinoate,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)CC1	3047.3	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O)C(C)(C)C(O[Si](C)(C)C(C)(C)C)=CC1	3058.2	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C(C)(C)C)=CC1	3266.2	Semi standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C(C)(C)C)=CC1	3016.0	Standard non polar	33892256
4-Oxo-13-cis-retinoate,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)C(O[Si](C)(C)C(C)(C)C)=CC1	3089.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxo-13-cis-retinoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2090000000-1c5451b849e980e311b0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxo-13-cis-retinoate GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3029000000-b04d7c59fc3ce4973812	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxo-13-cis-retinoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 10V, Positive-QTOF	splash10-00kb-0391000000-8caaf7c4c017bddfdaa6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 20V, Positive-QTOF	splash10-0002-1980000000-af3a5fdeff98e8840ec4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 40V, Positive-QTOF	splash10-0kbk-4910000000-1506f3079c815eac1226	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 10V, Negative-QTOF	splash10-03xr-0089000000-7665fb8471756952e98c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 20V, Negative-QTOF	splash10-02ta-0094000000-c917b32286fab5a78c61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 40V, Negative-QTOF	splash10-0uxv-6290000000-55b32ed2f34d92f67cfa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 10V, Negative-QTOF	splash10-03di-0079000000-16a7e691d9676e7c84c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 20V, Negative-QTOF	splash10-0gb9-0290000000-83e5e9702daddae492f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 40V, Negative-QTOF	splash10-016r-4910000000-e94b1001e037759106b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 10V, Positive-QTOF	splash10-014j-0392000000-83a2fc1baaa988e42e55	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 20V, Positive-QTOF	splash10-0fbj-0490000000-53eac69477af49e3a40d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-13-cis-retinoate 40V, Positive-QTOF	splash10-000i-4910000000-14c7b29334f7c8138747	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029175

KNApSAcK ID

Not Available

Chemspider ID

8171361

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9995780

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 4-Oxo-13-cis-retinoate (HMDB0012789)

MOL for HMDB0012789 (4-Oxo-13-cis-retinoate)

3D MOL for HMDB0012789 (4-Oxo-13-cis-retinoate)

3D SDF for HMDB0012789 (4-Oxo-13-cis-retinoate)

3D-SDF for HMDB0012789 (4-Oxo-13-cis-retinoate)

PDB for HMDB0012789 (4-Oxo-13-cis-retinoate)

3D PDB for HMDB0012789 (4-Oxo-13-cis-retinoate)

SMILES for HMDB0012789 (4-Oxo-13-cis-retinoate)

INCHI for HMDB0012789 (4-Oxo-13-cis-retinoate)

Structure for HMDB0012789 (4-Oxo-13-cis-retinoate)

3D Structure for HMDB0012789 (4-Oxo-13-cis-retinoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra