Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014602

Secondary Accession Numbers

HMDB14602

Metabolite Identification

Common Name

Acitretin

Description

Acitretin is only found in individuals that have used or taken this drug. It is an oral retinoid effective in the treatment of psoriasis. It is the major metabolite of etretinate with the advantage of a much shorter half-life when compared with etretinate (PubChem). The mechanism of action of acitretin is unknown, however it is believed to work by targeting specific receptors (retinoid receptors such as RXR and RAR) in the skin which help normalize the growth cycle of skin cells.

Structure

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

HMDB0014602
     RDKit          3D
Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.5563   -0.7913   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7567    0.1841    0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    0.0992    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.8893   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -0.9908   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -2.1571   -1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697    0.0395    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744   -0.0230    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -0.2355   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.4847   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -1.2612   -1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0573    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6563   -0.2137   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671    0.2871    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589    0.0896    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536   -0.6083   -1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062    0.6240    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4171    0.4592    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.1861   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2919    1.1023    1.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.0881    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    2.1762    1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    1.1369    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4335    2.2240    1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2800   -1.0464   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6379   -0.5176   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.7581    0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2350   -1.6999   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -2.9538   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -1.9095   -2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.5235   -0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.4642    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8365   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -1.6938   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.5609   -2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4463   -2.0178   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    0.6652    1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.8122   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3696    0.9087    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6235   -0.4742   -1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988   -1.6609   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3133   -0.1216   -1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    1.2308    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6334    0.5139    2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055    2.1471    2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2561    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    3.1634    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907    2.9596    1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0578    2.7571    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.7940    2.1107 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


  Mrv1652307191923542D          

 24 24  0  0  0  0            999 V2000
 9998.649210000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3637 9999.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.077810000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7933 9999.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.506810000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2224 9999.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.935910000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6535 9999.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.367010000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.0825 9999.9902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.367010001.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.935910001.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.077810001.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.222210001.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.791110000.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6492 9998.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7911 9998.7525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.9374 9999.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9353 9999.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.220910000.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5063 9999.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5063 9999.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2208 9998.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9353 9999.1655    0.0000 C   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 13  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
  7  8  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 19  1  0  0  0  0
  1 19  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 17  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014602

> <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-AQFIFDHZSA-N

> <FORMULA>
C21H26O3

> <MOLECULAR_WEIGHT>
326.4293

> <EXACT_MASS>
326.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.576298292691945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,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>
acitretin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014602
     RDKit          3D
Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.5563   -0.7913   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7567    0.1841    0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    0.0992    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.8893   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -0.9908   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -2.1571   -1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697    0.0395    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744   -0.0230    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -0.2355   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.4847   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -1.2612   -1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0573    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6563   -0.2137   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671    0.2871    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589    0.0896    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536   -0.6083   -1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062    0.6240    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4171    0.4592    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.1861   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2919    1.1023    1.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.0881    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    2.1762    1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    1.1369    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4335    2.2240    1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2800   -1.0464   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6379   -0.5176   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.7581    0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2350   -1.6999   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -2.9538   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -1.9095   -2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.5235   -0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.4642    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8365   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -1.6938   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.5609   -2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4463   -2.0178   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    0.6652    1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.8122   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3696    0.9087    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6235   -0.4742   -1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988   -1.6609   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3133   -0.1216   -1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    1.2308    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6334    0.5139    2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055    2.1471    2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2561    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    3.1634    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907    2.9596    1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0578    2.7571    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.7940    2.1107 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                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8664.1458667.418   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8665.4798666.648   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.8128667.418   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.1478666.648   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.4798667.418   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.8158666.648   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8672.1478667.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8673.4878666.648   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8674.8188667.418   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8676.1548666.648   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8674.8188668.958   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8672.1478668.958   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.8128668.958   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.4818668.958   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8658.8108667.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.1458664.338   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8658.8108664.338   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8657.2168665.259   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8662.8138666.649   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.4798667.419   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8660.1458666.649   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8660.1458665.109   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8661.4798664.339   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8662.8138665.109   0.000  0.00  0.00           C+0
CONECT    1    2   19                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7                                                            
CONECT   13    3                                                            
CONECT   14   20                                                            
CONECT   15   21                                                            
CONECT   16   24                                                            
CONECT   17   18   22                                                       
CONECT   18   17                                                            
CONECT   19   20   24    1                                                  
CONECT   20   19   21   14                                                  
CONECT   21   20   22   15                                                  
CONECT   22   21   23   17                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19   16                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0014602
HETATM    1  C1  UNL     1      -7.556  -0.791  -0.388  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.757   0.184   0.200  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.371   0.099   0.158  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.678  -0.889  -0.426  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.306  -0.991  -0.474  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.630  -2.157  -1.107  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.570   0.039   0.150  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.174  -0.023   0.062  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.050  -0.235  -0.225  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.266  -0.485  -0.560  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.728  -1.261  -1.741  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.274   0.057   0.176  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.656  -0.214  -0.213  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.667   0.287   0.490  1.00  0.00           C  
HETATM   15  C14 UNL     1       6.059   0.090   0.197  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.454  -0.608  -1.054  1.00  0.00           C  
HETATM   17  C16 UNL     1       7.006   0.624   0.978  1.00  0.00           C  
HETATM   18  C17 UNL     1       8.417   0.459   0.751  1.00  0.00           C  
HETATM   19  O2  UNL     1       8.953  -0.186  -0.148  1.00  0.00           O  
HETATM   20  O3  UNL     1       9.292   1.102   1.645  1.00  0.00           O  
HETATM   21  C18 UNL     1      -3.293   1.088   0.772  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.503   2.176   1.399  1.00  0.00           C  
HETATM   23  C20 UNL     1      -4.653   1.137   0.787  1.00  0.00           C  
HETATM   24  C21 UNL     1      -5.434   2.224   1.409  1.00  0.00           C  
HETATM   25  H1  UNL     1      -7.280  -1.046  -1.430  1.00  0.00           H  
HETATM   26  H2  UNL     1      -8.638  -0.518  -0.388  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.439  -1.758   0.198  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.235  -1.700  -0.931  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.423  -2.954  -1.140  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.438  -1.910  -2.159  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.763  -2.523  -0.527  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.836   0.464   1.270  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.485  -0.837  -1.446  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.915  -1.694  -2.338  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.273  -0.561  -2.441  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.446  -2.018  -1.404  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.019   0.665   1.009  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.912  -0.812  -1.068  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.370   0.909   1.372  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.624  -0.474  -1.808  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.599  -1.661  -0.879  1.00  0.00           H  
HETATM   42  H18 UNL     1       7.313  -0.122  -1.579  1.00  0.00           H  
HETATM   43  H19 UNL     1       6.632   1.231   1.822  1.00  0.00           H  
HETATM   44  H20 UNL     1       9.633   0.514   2.408  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.506   2.147   2.497  1.00  0.00           H  
HETATM   46  H22 UNL     1      -1.476   2.256   0.995  1.00  0.00           H  
HETATM   47  H23 UNL     1      -2.975   3.163   1.103  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.791   2.960   1.898  1.00  0.00           H  
HETATM   49  H25 UNL     1      -6.058   2.757   0.633  1.00  0.00           H  
HETATM   50  H26 UNL     1      -6.191   1.794   2.111  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

HMDB0014602
     RDKit          3D
Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -7.5563   -0.7913   -0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7567    0.1841    0.1999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    0.0992    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.8893   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -0.9908   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -2.1571   -1.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697    0.0395    0.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744   -0.0230    0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -0.2355   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.4847   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281   -1.2612   -1.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739    0.0573    0.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6563   -0.2137   -0.2134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6671    0.2871    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0589    0.0896    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536   -0.6083   -1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0062    0.6240    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4171    0.4592    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9533   -0.1861   -0.1481 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2919    1.1023    1.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.0881    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034    2.1762    1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6534    1.1369    0.7867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4335    2.2240    1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2800   -1.0464   -1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6379   -0.5176   -0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.7581    0.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2350   -1.6999   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4231   -2.9538   -1.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4379   -1.9095   -2.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.5235   -0.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    0.4642    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.8365   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -1.6938   -2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727   -0.5609   -2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4463   -2.0178   -1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    0.6652    1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9119   -0.8122   -1.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3696    0.9087    1.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6235   -0.4742   -1.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988   -1.6609   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3133   -0.1216   -1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6322    1.2308    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6334    0.5139    2.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055    2.1471    2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2561    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    3.1634    1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907    2.9596    1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0578    2.7571    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1912    1.7940    2.1107 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
(all-e)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	ChEBI
Acitretina	ChEBI
Acitretine	ChEBI
Acitretinum	ChEBI
all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid	ChEBI
Etretin	ChEBI
Neotigason	ChEBI
Soriatane	ChEBI
(all-e)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate	Generator
all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoate	Generator
Isoacitretin	HMDB
13-cis-Acitretin	HMDB
Acitretin, (Z,e,e,e)-isomer	HMDB
Isoetretin	HMDB
Acetretin	HMDB
Acitretin andreu brand	HMDB
Acitretin roche brand	HMDB
Hoffmann la roche brand OF acitretin	HMDB
Hoffmann-la roche brand OF acitretin	HMDB
Andreu brand OF acitretin	HMDB
Roche brand OF acitretin	HMDB
(2E,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid	HMDB
Acitretinoin	HMDB
all-trans-Acitretin	HMDB
Acitretin	HMDB

Chemical Formula

C₂₁H₂₆O₃

Average Molecular Weight

326.4293

Monoisotopic Molecular Weight

326.188194698

IUPAC Name

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

Traditional Name

acitretin

CAS Registry Number

55079-83-9

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-AQFIFDHZSA-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

retinoid (CHEBI:50173 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:50173 )
acitretin (CHEBI:50173 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014602)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 - 230 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00048 g/L	Not Available
LogP	5.7	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	38.58 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]+	182.659	31661259
DarkChem	[M-H]-	188.527	31661259
DeepCCS	[M+H]+	200.221	30932474
DeepCCS	[M-H]-	197.863	30932474
DeepCCS	[M-2H]-	231.812	30932474
DeepCCS	[M+Na]+	207.041	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	330.9 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
Acitretin	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
Acitretin	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
Acitretin	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
Acitretin,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
Acitretin,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 - Acitretin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1279000000-d74bbc0348cfdb3b3732	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acitretin GC-MS (1 TMS) - 70eV, Positive	splash10-001i-4139000000-85e857f30a345651bb66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acitretin 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 - Acitretin LC-ESI-qTof , Positive-QTOF	splash10-01t9-0592000000-92a48c620c961fdb430f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acitretin , positive-QTOF	splash10-056r-1943000000-77c18bcac662a9f6bdcb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Acitretin , positive-QTOF	splash10-056r-2942000000-57cdf186555912258599	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 10V, Positive-QTOF	splash10-05r0-0389000000-28f8ff224c8fd7ac1606	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 20V, Positive-QTOF	splash10-02t9-0690000000-11440b22373ebd567609	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 40V, Positive-QTOF	splash10-114j-4920000000-bf257c11adfb644686f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 10V, Negative-QTOF	splash10-004i-0059000000-2338c505b394d676d7a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 20V, Negative-QTOF	splash10-0059-0097000000-d73443e0cee4f07fd0d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 40V, Negative-QTOF	splash10-066r-3391000000-8adb8a7f90aecb16b198	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 10V, Negative-QTOF	splash10-001j-0092000000-da6b1640ed88e8dd0629	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 20V, Negative-QTOF	splash10-017j-1291000000-8d03b8e6cfa817060924	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 40V, Negative-QTOF	splash10-00dj-1494000000-45aa9916567486569a90	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 10V, Positive-QTOF	splash10-0ke9-0395000000-2d28d3c86a8a16a5adac	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 20V, Positive-QTOF	splash10-03di-0940000000-2f4d9396336fd697861e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acitretin 40V, Positive-QTOF	splash10-00tf-1900000000-f5a87d3a7b17af3487e6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB00459	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00459	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00459

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023099

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acitretin

METLIN ID

Not Available

PubChem Compound

5284513

PDB ID

Not Available

ChEBI ID

50173

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.

Enzymes

Enzyme Details

1. Retinoic acid receptor gamma

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: This is a receptor for retinoic acid. This metabolite has profound effects on vertebrate development. Retinoic acid is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression
Gene Name:: RARG
Uniprot ID:: P13631
Molecular weight:: 50341.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Retinoic acid receptor alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: This is a receptor for retinoic acid. Retinoic acid has profound effects on vertebrate development, is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression. Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing MLL5. Mediates retinoic acid-induced granulopoiesis
Gene Name:: RARA
Uniprot ID:: P10276
Molecular weight:: 50770.8

References

Saurat JH: Retinoids and psoriasis: novel issues in retinoid pharmacology and implications for psoriasis treatment. J Am Acad Dermatol. 1999 Sep;41(3 Pt 2):S2-6. [PubMed:10459139 ]
Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [PubMed:9074840 ]
Tian K, Norris AW, Lin CL, Li E: The isolation and characterization of purified heterocomplexes of recombinant retinoic acid receptor and retinoid X receptor ligand binding domains. Biochemistry. 1997 May 13;36(19):5669-76. [PubMed:9153406 ]
Tippmann F, Hundt J, Schneider A, Endres K, Fahrenholz F: Up-regulation of the alpha-secretase ADAM10 by retinoic acid receptors and acitretin. FASEB J. 2009 Jun;23(6):1643-54. doi: 10.1096/fj.08-121392. Epub 2009 Jan 14. [PubMed:19144697 ]

Enzyme Details

3. Cytochrome P450 26A1

General function:: Involved in monooxygenase activity
Specific function:: Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18- hydroxylation. Responsible for generation of several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA and 18-OH-RA
Gene Name:: CYP26A1
Uniprot ID:: O43174
Molecular weight:: 56198.1

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Retinoic acid receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: This is a receptor for retinoic acid. This metabolite has profound effects on vertebrate development. Retinoic acid is a morphogen and is a powerful teratogen. This receptor controls cell function by directly regulating gene expression
Gene Name:: RARB
Uniprot ID:: P10826
Molecular weight:: 50488.6

References

Berggren Soderlund M, Johannesson G, Fex G: Expression of human all-trans-retinoic acid receptor beta and its ligand-binding domain in Escherichia coli. Biochem J. 1995 May 15;308 ( Pt 1):353-9. [PubMed:7755585 ]
Zouboulis CC: Retinoids--which dermatological indications will benefit in the near future? Skin Pharmacol Appl Skin Physiol. 2001 Sep-Oct;14(5):303-15. [PubMed:11586072 ]
Tippmann F, Hundt J, Schneider A, Endres K, Fahrenholz F: Up-regulation of the alpha-secretase ADAM10 by retinoic acid receptors and acitretin. FASEB J. 2009 Jun;23(6):1643-54. doi: 10.1096/fj.08-121392. Epub 2009 Jan 14. [PubMed:19144697 ]

Enzyme Details

5. Retinoic acid receptor RXR-beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)
Gene Name:: RXRB
Uniprot ID:: P28702
Molecular weight:: 56921.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

6. Retinoic acid receptor RXR-gamma

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)
Gene Name:: RXRG
Uniprot ID:: P48443
Molecular weight:: 50870.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [PubMed:9074840 ]

Enzyme Details

7. Retinoic acid receptor RXR-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA). ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer
Gene Name:: RXRA
Uniprot ID:: P19793
Molecular weight:: 50810.8

References

Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [PubMed:9074840 ]
Tian K, Norris AW, Lin CL, Li E: The isolation and characterization of purified heterocomplexes of recombinant retinoic acid receptor and retinoid X receptor ligand binding domains. Biochemistry. 1997 May 13;36(19):5669-76. [PubMed:9153406 ]

Enzyme Details

8. Retinol-binding protein 1

General function:: Involved in binding
Specific function:: Intracellular transport of retinol
Gene Name:: RBP1
Uniprot ID:: P09455
Molecular weight:: 15850.1

References

Berni R, Clerici M, Malpeli G, Cleris L, Formelli F: Retinoids: in vitro interaction with retinol-binding protein and influence on plasma retinol. FASEB J. 1993 Sep;7(12):1179-84. [PubMed:8375617 ]

Showing metabocard for Acitretin (HMDB0014602)

MOL for HMDB0014602 (Acitretin)

3D MOL for HMDB0014602 (Acitretin)

3D SDF for HMDB0014602 (Acitretin)

3D-SDF for HMDB0014602 (Acitretin)

PDB for HMDB0014602 (Acitretin)

3D PDB for HMDB0014602 (Acitretin)

SMILES for HMDB0014602 (Acitretin)

INCHI for HMDB0014602 (Acitretin)

Structure for HMDB0014602 (Acitretin)

3D Structure for HMDB0014602 (Acitretin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References