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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:28 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003039

Secondary Accession Numbers

HMDB03039

Metabolite Identification

Common Name

Isoacitretin

Description

Isoacitretin, also known as 13-cis-acitretin or soriatane, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Based on a literature review a significant number of articles have been published on Isoacitretin.

Structure

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

HMDB0003039
     RDKit          3D
Isoacitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.3932    0.6092   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5355    0.8455    0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804    0.5810   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.1044   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079   -0.1602   -1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764   -0.6758   -2.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4030    0.0483   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.2983   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.0093    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.4304   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.2416   -1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515   -0.0646    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -0.4856    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.1002    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057   -0.5555    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2688   -1.3930   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2031   -0.2626    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2407    0.5251    2.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862    0.7417    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1958    1.0960    2.8837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    0.5174    0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1008    0.7139    2.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.7847    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397    1.3041    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0805    1.3358   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2466   -0.4102   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    0.8035   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297   -0.0628   -2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0615    0.0357   -3.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -0.7571   -3.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.6965   -2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -0.9493   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.6321    0.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1760   -2.2007   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -0.7136   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -1.4197   -2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796    0.5551    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9229   -1.0897   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4989    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2911   -1.7558   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0127   -0.8044   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -2.3045   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1862   -0.6451    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602    2.0142    3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603   -0.1341    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.7627    2.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6901    2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584    1.7098    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655    0.5269    2.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2153    2.1843    2.5381 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  7 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23  3  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
M  END


  Mrv1652306121923322D          

 24 24  0  0  0  0            999 V2000
 9998.589110000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3036 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.017210000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7329 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.446610000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1623 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.875910000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.017210001.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.162210001.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.731310000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5891 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7313 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8776 9999.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.875410000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.160910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.446410000.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4463 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1608 9998.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8754 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.875510001.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.590610000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5910 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8768 9998.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.3057 9998.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  1 14  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 19 11  1  0  0  0  0
  7 20  1  0  0  0  0
  7 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003039

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12-

> <INCHI_KEY>
IHUNBGSDBOWDMA-UGOGCBOOSA-N

> <FORMULA>
C21H26O3

> <MOLECULAR_WEIGHT>
326.4293

> <EXACT_MASS>
326.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.3854790417451

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
5.5870487256666665

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.011075936120913

> <JCHEM_PKA_STRONGEST_BASIC>
-4.820120196843592

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
104.16649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.78e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetretin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003039
     RDKit          3D
Isoacitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.3932    0.6092   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5355    0.8455    0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804    0.5810   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.1044   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079   -0.1602   -1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764   -0.6758   -2.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4030    0.0483   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.2983   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.0093    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.4304   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.2416   -1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515   -0.0646    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -0.4856    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.1002    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057   -0.5555    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2688   -1.3930   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2031   -0.2626    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2407    0.5251    2.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862    0.7417    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1958    1.0960    2.8837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    0.5174    0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1008    0.7139    2.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.7847    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397    1.3041    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0805    1.3358   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2466   -0.4102   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    0.8035   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297   -0.0628   -2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0615    0.0357   -3.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -0.7571   -3.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.6965   -2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -0.9493   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.6321    0.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1760   -2.2007   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -0.7136   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -1.4197   -2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796    0.5551    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9229   -1.0897   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4989    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2911   -1.7558   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0127   -0.8044   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -2.3045   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1862   -0.6451    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602    2.0142    3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603   -0.1341    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.7627    2.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6901    2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584    1.7098    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655    0.5269    2.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2153    2.1843    2.5381 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  7 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23  3  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
M  END

HEADER    PROTEIN                                 12-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JUN-19         0                                  
HETATM    1  C   UNK     0    8664.0338667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.3678666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.6998667.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.0358666.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.3678667.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.7038666.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.0358667.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.6998668.977   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3698668.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8658.6988667.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0338664.356   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8658.6988664.356   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8657.1058665.277   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7018666.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.3678667.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.0338666.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.0338665.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.3678664.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.7018665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8672.0348668.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8673.3698666.667   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.3708665.127   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8672.0378664.357   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8674.7048664.358   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   20   21                                                  
CONECT    8    3                                                            
CONECT    9   15                                                            
CONECT   10   16                                                            
CONECT   11   19                                                            
CONECT   12   13   17                                                       
CONECT   13   12                                                            
CONECT   14   15   19    1                                                  
CONECT   15   14   16    9                                                  
CONECT   16   15   17   10                                                  
CONECT   17   16   18   12                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   11                                                  
CONECT   20    7                                                            
CONECT   21    7   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0003039
HETATM    1  C1  UNL     1      -7.393   0.609  -1.077  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.535   0.846   0.047  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.180   0.581  -0.094  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.637   0.104  -1.263  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.308  -0.160  -1.421  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.776  -0.676  -2.723  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.403   0.048  -0.364  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.026  -0.298  -0.626  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.068  -0.009   0.015  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.414  -0.430  -0.355  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.684  -1.242  -1.535  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.452  -0.065   0.398  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.778  -0.486   0.025  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.809  -0.100   0.807  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.106  -0.556   0.375  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.269  -1.393  -0.856  1.00  0.00           C  
HETATM   17  C16 UNL     1       7.203  -0.263   1.031  1.00  0.00           C  
HETATM   18  C17 UNL     1       7.241   0.525   2.226  1.00  0.00           C  
HETATM   19  O2  UNL     1       8.386   0.742   2.775  1.00  0.00           O  
HETATM   20  O3  UNL     1       6.196   1.096   2.884  1.00  0.00           O  
HETATM   21  C18 UNL     1      -2.926   0.517   0.801  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.101   0.714   2.031  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.305   0.785   0.939  1.00  0.00           C  
HETATM   24  C21 UNL     1      -4.840   1.304   2.221  1.00  0.00           C  
HETATM   25  H1  UNL     1      -7.080   1.336  -1.860  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.247  -0.410  -1.481  1.00  0.00           H  
HETATM   27  H3  UNL     1      -8.442   0.804  -0.824  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.330  -0.063  -2.097  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.062   0.036  -3.182  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.627  -0.757  -3.435  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.375  -1.696  -2.591  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.816  -0.949  -1.523  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.018   0.632   0.874  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.176  -2.201  -1.210  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.466  -0.714  -2.181  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.859  -1.420  -2.217  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.280   0.555   1.296  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.923  -1.090  -0.852  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.567   0.499   1.661  1.00  0.00           H  
HETATM   40  H16 UNL     1       7.291  -1.756  -0.944  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.013  -0.804  -1.755  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.618  -2.304  -0.814  1.00  0.00           H  
HETATM   43  H19 UNL     1       8.186  -0.645   0.645  1.00  0.00           H  
HETATM   44  H20 UNL     1       6.260   2.014   3.279  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.460  -0.134   2.285  1.00  0.00           H  
HETATM   46  H22 UNL     1      -2.815   0.763   2.925  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.602   1.690   2.012  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.858   1.710   2.084  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.866   0.527   2.989  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.215   2.184   2.538  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6    7    7
CONECT    6   29   30   31
CONECT    7    8   21
CONECT    8    9    9   32
CONECT    9   10   33
CONECT   10   11   12   12
CONECT   11   34   35   36
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   39
CONECT   15   16   17   17
CONECT   16   40   41   42
CONECT   17   18   43
CONECT   18   19   19   20
CONECT   20   44
CONECT   21   22   23   23
CONECT   22   45   46   47
CONECT   23   24
CONECT   24   48   49   50
END

HMDB0003039
     RDKit          3D
Isoacitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.3932    0.6092   -1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5355    0.8455    0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1804    0.5810   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.1044   -1.2629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079   -0.1602   -1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7764   -0.6758   -2.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4030    0.0483   -0.3644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -0.2983   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0684   -0.0093    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.4304   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6842   -1.2416   -1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515   -0.0646    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778   -0.4856    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8090   -0.1002    0.8065 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057   -0.5555    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2688   -1.3930   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2031   -0.2626    1.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2407    0.5251    2.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3862    0.7417    2.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1958    1.0960    2.8837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    0.5174    0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1008    0.7139    2.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3045    0.7847    0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8397    1.3041    2.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0805    1.3358   -1.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2466   -0.4102   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4420    0.8035   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297   -0.0628   -2.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0615    0.0357   -3.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6269   -0.7571   -3.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.6965   -2.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -0.9493   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181    0.6321    0.8740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1760   -2.2007   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -0.7136   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8590   -1.4197   -2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2796    0.5551    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9229   -1.0897   -0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4989    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2911   -1.7558   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0127   -0.8044   -1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -2.3045   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1862   -0.6451    0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2602    2.0142    3.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603   -0.1341    2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8150    0.7627    2.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024    1.6901    2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8584    1.7098    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8655    0.5269    2.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2153    2.1843    2.5381 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  7 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23  3  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 20 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-cis-Acitretin	HMDB
13-cis-Etretin	HMDB
Soriatane	HMDB
Acitretin	HMDB
Acitretin andreu brand	HMDB
Acitretin roche brand	HMDB
Acitretin, (Z,e,e,e)-isomer	HMDB
Andreu brand OF acitretin	HMDB
Etretin	HMDB
Hoffmann la roche brand OF acitretin	HMDB
Hoffmann-la roche brand OF acitretin	HMDB
Isoetretin	HMDB
Neotigason	HMDB
Roche brand OF acitretin	HMDB
(2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	HMDB
Isoacitretin	MeSH

Chemical Formula

C₂₁H₂₆O₃

Average Molecular Weight

326.4293

Monoisotopic Molecular Weight

326.188194698

IUPAC Name

(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

Traditional Name

acetretin

CAS Registry Number

69427-46-9

SMILES

COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1

InChI Identifier

InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12-

InChI Key

IHUNBGSDBOWDMA-UGOGCBOOSA-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
Retinoid skeleton
Sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Medium-chain fatty acid
Styrene
Alkyl aryl ether
Branched fatty acid
Methyl-branched fatty acid
Monocyclic benzene moiety
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acitretin (CHEBI:50174 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Tissue

Epithelium

Epidermis (HMDB: HMDB0003039)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003039)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003039)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003039)

Source

Exogenous

Food

Food (HMDB: HMDB0003039)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0003039)

Endogenous

Endogenous (HMDB: HMDB0003039)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003039)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003039)

Lipid metabolism pathway (HMDB: HMDB0003039)

Cellular process

Cell signaling (HMDB: HMDB0003039)

Biochemical process

Lipid transport (HMDB: HMDB0003039)

Role

Biological role

Energy source (HMDB: HMDB0003039)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003039)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003039)

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	0.00048 g/L	ALOGPS
logP	5.2	ALOGPS
logP	5.59	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.17 m³·mol⁻¹	ChemAxon
Polarizability	38.39 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.613	31661259
DarkChem	[M-H]-	187.449	31661259
DeepCCS	[M+H]+	200.965	30932474
DeepCCS	[M-H]-	198.607	30932474
DeepCCS	[M-2H]-	232.491	30932474
DeepCCS	[M+Na]+	207.719	30932474
AllCCS	[M+H]+	182.1	32859911
AllCCS	[M+H-H2O]+	179.0	32859911
AllCCS	[M+NH4]+	185.0	32859911
AllCCS	[M+Na]+	185.9	32859911
AllCCS	[M-H]-	182.5	32859911
AllCCS	[M+Na-2H]-	182.6	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.97 minutes	32390414
Predicted by Siyang on May 30, 2022	24.1107 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3084.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	709.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	281.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	445.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1034.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	940.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2159.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	804.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1867.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	735.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	541.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	535.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoacitretin	COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1	4261.6	Standard polar	33892256
Isoacitretin	COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1	2744.4	Standard non polar	33892256
Isoacitretin	COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C/C(O)=O)C(C)=C1	3028.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoacitretin,1TMS,isomer #1	COC1=CC(C)=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O[Si](C)(C)C)C(C)=C1C	2952.1	Semi standard non polar	33892256
Isoacitretin,1TBDMS,isomer #1	COC1=CC(C)=C(/C=C/C(C)=C/C=C/C(C)=C\C(=O)O[Si](C)(C)C(C)(C)C)C(C)=C1C	3180.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoacitretin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1279000000-d74bbc0348cfdb3b3732	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoacitretin GC-MS (1 TMS) - 70eV, Positive	splash10-001i-4139000000-85e857f30a345651bb66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoacitretin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoacitretin LC-ESI-qTof , Positive-QTOF	splash10-01t9-0592000000-92a48c620c961fdb430f	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoacitretin , positive-QTOF	splash10-056r-1943000000-77c18bcac662a9f6bdcb	2018-05-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoacitretin , positive-QTOF	splash10-056r-2942000000-57cdf186555912258599	2018-05-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Positive-QTOF	splash10-0a4i-0369000000-c76928c945feff099218	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Positive-QTOF	splash10-0aor-0970000000-83c7baa1aeda7da5a2cb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Positive-QTOF	splash10-0pvi-4910000000-b657ca2b064b9ff56256	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Negative-QTOF	splash10-0059-0049000000-4a4ee208619c94b4e2c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Negative-QTOF	splash10-057i-0079000000-35044b92edd7238b81e3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Negative-QTOF	splash10-066u-2291000000-5bb79aadc2928c46ff88	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Negative-QTOF	splash10-001j-0092000000-da6b1640ed88e8dd0629	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Negative-QTOF	splash10-017j-1291000000-8d03b8e6cfa817060924	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Negative-QTOF	splash10-00dj-1494000000-45aa9916567486569a90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 10V, Positive-QTOF	splash10-0ke9-0395000000-2d28d3c86a8a16a5adac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 20V, Positive-QTOF	splash10-03di-0940000000-2f4d9396336fd697861e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoacitretin 40V, Positive-QTOF	splash10-00tf-1900000000-f5a87d3a7b17af3487e6	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Epidermis

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

FDB023099

KNApSAcK ID

Not Available

Chemspider ID

4942363

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

621

PubChem Compound

6437841

PDB ID

Not Available

ChEBI ID

50174

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Mestres Quadreny, Ramon; Tortajada Lopez, Desamparados; Arrell Piquer, Maria Jose; Parra Alvarez, Margarita; Gil Grau, Salvador; Cetta Builelo, Luisa; Simo Planells, Ana. Process for the preparation of aromatic retinoic acids [e.g., etretin] and their derivatives. Span. (1992), 14 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Al-Mallah NR, Bun H, Coassolo P, Aubert C, Cano JP: Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography. J Chromatogr. 1987 Oct 9;421(1):177-86. [PubMed:2963014 ]
Vane FM, Bugge JL, Rodriguez LC: Identification of etretinate metabolites in human blood. Drug Metab Dispos. 1989 May-Jun;17(3):280-5. [PubMed:2568909 ]
Fayer BE, Huselton CA, Garland WA, Liberato DJ: Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. J Chromatogr. 1991 Jul 17;568(1):135-44. [PubMed:1837553 ]
Vane FM, Bugge CJ, Rodriguez LC: Identification of etretinate metabolites in human bile. Drug Metab Dispos. 1989 May-Jun;17(3):275-9. [PubMed:2568908 ]
De Leenheer AP, Lambert WE, De Bersaques JP, Kint AH: High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. J Chromatogr. 1990 Feb 2;500:637-42. [PubMed:2139439 ]
Larsen FG, Vahlquist C, Andersson E, Torma H, Kragballe K, Vahlquist A: Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. Acta Derm Venereol. 1992;72(2):84-8. [PubMed:1350412 ]

Showing metabocard for Isoacitretin (HMDB0003039)

MOL for HMDB0003039 (Isoacitretin)

3D MOL for HMDB0003039 (Isoacitretin)

3D SDF for HMDB0003039 (Isoacitretin)

3D-SDF for HMDB0003039 (Isoacitretin)

PDB for HMDB0003039 (Isoacitretin)

3D PDB for HMDB0003039 (Isoacitretin)

SMILES for HMDB0003039 (Isoacitretin)

INCHI for HMDB0003039 (Isoacitretin)

Structure for HMDB0003039 (Isoacitretin)

3D Structure for HMDB0003039 (Isoacitretin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra