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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:35:21 UTC

Update Date

2021-09-26 22:57:21 UTC

HMDB ID

HMDB0247585

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-cis Acitretin

Description

9-cis Acitretin, also known as etretin or isoacitretin, 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 very few articles have been published on 9-cis Acitretin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9-cis acitretin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9-cis Acitretin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247585
     RDKit          3D
9-cis Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -6.8410   -0.3207    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7569   -0.0030    0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.2428    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278    0.2163    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    0.4820    2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.4419    3.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    0.7551    1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.0224    2.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    0.7842    1.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937    0.5061    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1604    0.9178    2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0883   -0.0345    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213   -0.3590   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.7986   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730   -1.2475   -2.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.2630   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.6542   -3.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2938   -2.0653   -4.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -2.3762   -5.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244   -2.4163   -5.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1804    0.7800    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.2753   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.5269   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965    0.4993   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5206    0.5339    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -1.2052    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5846   -0.6788    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755    0.0072    2.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    0.5672    4.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -0.6005    4.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.1896    4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6326    1.5103    3.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    1.6872    2.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.0533    2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341    1.6460    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7696    1.5375    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -0.3553   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -0.0421    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -0.7623   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4811   -2.0363   -2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220   -0.2769   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9158   -1.5955   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.6624   -3.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863   -1.4577   -6.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.8410   -1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.5637   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616    2.1560   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006    0.8798   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540   -0.5264   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    1.1149   -1.7695 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  3
  9 10  1  0
 10 11  1  0
 10 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 15 17  2  3
 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


  Mrv1652309112102352D          

 24 24  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  4  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
  6 21  1  0  0  0  0
  5 22  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247585

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C)C(C)=C(C=CC(C)=CC=CC(C)=CC(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)

> <INCHI_KEY>
IHUNBGSDBOWDMA-UHFFFAOYSA-N

> <FORMULA>
C21H26O3

> <MOLECULAR_WEIGHT>
326.436

> <EXACT_MASS>
326.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.74403642765614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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

$$$$

HMDB0247585
     RDKit          3D
9-cis Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -6.8410   -0.3207    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7569   -0.0030    0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.2428    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278    0.2163    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    0.4820    2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.4419    3.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    0.7551    1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.0224    2.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    0.7842    1.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937    0.5061    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1604    0.9178    2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0883   -0.0345    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213   -0.3590   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.7986   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730   -1.2475   -2.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.2630   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.6542   -3.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2938   -2.0653   -4.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -2.3762   -5.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244   -2.4163   -5.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1804    0.7800    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.2753   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.5269   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965    0.4993   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5206    0.5339    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -1.2052    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5846   -0.6788    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755    0.0072    2.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    0.5672    4.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -0.6005    4.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.1896    4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6326    1.5103    3.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    1.6872    2.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.0533    2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341    1.6460    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7696    1.5375    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -0.3553   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -0.0421    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -0.7623   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4811   -2.0363   -2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220   -0.2769   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9158   -1.5955   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.6624   -3.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863   -1.4577   -6.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.8410   -1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.5637   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616    2.1560   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006    0.8798   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540   -0.5264   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    1.1149   -1.7695 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  3
  9 10  1  0
 10 11  1  0
 10 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 15 17  2  3
 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                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   22                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14                                                            
CONECT   20   10                                                            
CONECT   21    6                                                            
CONECT   22    5                                                            
CONECT   23    4   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0247585
HETATM    1  C1  UNL     1      -6.841  -0.321   1.028  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.757  -0.003   0.220  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.478   0.243   0.700  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.228   0.216   2.055  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.884   0.482   2.489  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.718   0.442   3.964  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.897   0.755   1.600  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.539   1.022   2.191  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.574   0.784   1.743  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.894   0.506   1.221  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.160   0.918   2.004  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.088  -0.034   0.117  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.721  -0.359  -0.386  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.415  -0.799  -1.553  1.00  0.00           C  
HETATM   15  C14 UNL     1       4.473  -1.247  -2.447  1.00  0.00           C  
HETATM   16  C15 UNL     1       5.875  -1.263  -1.999  1.00  0.00           C  
HETATM   17  C16 UNL     1       4.139  -1.654  -3.649  1.00  0.00           C  
HETATM   18  C17 UNL     1       5.294  -2.065  -4.484  1.00  0.00           C  
HETATM   19  O2  UNL     1       6.117  -2.376  -5.128  1.00  0.00           O  
HETATM   20  O3  UNL     1       4.224  -2.416  -5.775  1.00  0.00           O  
HETATM   21  C18 UNL     1      -2.180   0.780   0.271  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.199   1.275  -0.726  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.448   0.527  -0.209  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.796   0.499  -1.608  1.00  0.00           C  
HETATM   25  H1  UNL     1      -7.521   0.534   1.141  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.397  -1.205   0.592  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.585  -0.679   2.069  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.975   0.007   2.795  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.743   0.567   4.447  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.393  -0.600   4.243  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.016   1.190   4.308  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.633   1.510   3.214  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.119   1.687   2.651  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.645   0.053   2.379  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.734   1.646   1.418  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.770   1.537   2.878  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.480  -0.355  -0.637  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.023  -0.042   0.466  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.413  -0.762  -1.968  1.00  0.00           H  
HETATM   40  H16 UNL     1       6.481  -2.036  -2.549  1.00  0.00           H  
HETATM   41  H17 UNL     1       6.322  -0.277  -2.120  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.916  -1.595  -0.908  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.120  -1.662  -3.894  1.00  0.00           H  
HETATM   44  H20 UNL     1       4.086  -1.458  -6.109  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.701   1.841  -1.579  1.00  0.00           H  
HETATM   46  H22 UNL     1      -0.506   0.564  -1.101  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.662   2.156  -0.227  1.00  0.00           H  
HETATM   48  H24 UNL     1      -3.101   0.880  -2.349  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.154  -0.526  -1.939  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.734   1.115  -1.769  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

HMDB0247585
     RDKit          3D
9-cis Acitretin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -6.8410   -0.3207    1.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7569   -0.0030    0.2198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778    0.2428    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2278    0.2163    2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8842    0.4820    2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.4419    3.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    0.7551    1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5389    1.0224    2.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5736    0.7842    1.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937    0.5061    1.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1604    0.9178    2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0883   -0.0345    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7213   -0.3590   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -0.7986   -1.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4730   -1.2475   -2.4470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8749   -1.2630   -1.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1394   -1.6542   -3.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2938   -2.0653   -4.4837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -2.3762   -5.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244   -2.4163   -5.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1804    0.7800    0.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1993    1.2753   -0.7263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.5269   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965    0.4993   -1.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5206    0.5339    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3967   -1.2052    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5846   -0.6788    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755    0.0072    2.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428    0.5672    4.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3927   -0.6005    4.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0156    1.1896    4.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6326    1.5103    3.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187    1.6872    2.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6450    0.0533    2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341    1.6460    1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7696    1.5375    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4801   -0.3553   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234   -0.0421    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4130   -0.7623   -1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4811   -2.0363   -2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3220   -0.2769   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9158   -1.5955   -0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.6624   -3.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0863   -1.4577   -6.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.8410   -1.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5058    0.5637   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616    2.1560   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1006    0.8798   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1540   -0.5264   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    1.1149   -1.7695 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  3
  9 10  1  0
 10 11  1  0
 10 12  2  3
 12 13  1  0
 13 14  2  3
 14 15  1  0
 15 16  1  0
 15 17  2  3
 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
Acitretin	HMDB
Acitretin, (Z,e,e,e)-isomer	HMDB
Etretin	HMDB
Isoacitretin	HMDB
Isoetretin	HMDB
Neotigason	HMDB
Soriatane	HMDB

Chemical Formula

C₂₁H₂₆O₃

Average Molecular Weight

326.436

Monoisotopic Molecular Weight

326.188194697

IUPAC Name

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

Traditional Name

acitretin

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(C)=C(C=CC(C)=CC=CC(C)=CC(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)

InChI Key

IHUNBGSDBOWDMA-UHFFFAOYSA-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:50172 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	38.74 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
DeepCCS	[M+H]+	187.139	30932474
DeepCCS	[M-H]-	184.482	30932474
DeepCCS	[M-2H]-	219.307	30932474
DeepCCS	[M+Na]+	195.597	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-cis Acitretin	COC1=C(C)C(C)=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)=C1	4261.6	Standard polar	33892256
9-cis Acitretin	COC1=C(C)C(C)=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)=C1	2744.4	Standard non polar	33892256
9-cis Acitretin	COC1=C(C)C(C)=C(C=CC(C)=CC=CC(C)=CC(O)=O)C(C)=C1	3028.4	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 - 9-cis Acitretin GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-1279000000-d74bbc0348cfdb3b3732	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis Acitretin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis Acitretin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-cis Acitretin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 9-cis Acitretin 10V, Positive-QTOF	splash10-0ke9-0395000000-2d28d3c86a8a16a5adac	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Acitretin 20V, Positive-QTOF	splash10-03di-0940000000-2f4d9396336fd697861e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Acitretin 40V, Positive-QTOF	splash10-00tf-1900000000-f5a87d3a7b17af3487e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Acitretin 10V, Negative-QTOF	splash10-001j-0092000000-da6b1640ed88e8dd0629	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Acitretin 20V, Negative-QTOF	splash10-017j-1291000000-8d03b8e6cfa817060924	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-cis Acitretin 40V, Negative-QTOF	splash10-00dj-1494000000-45aa9916567486569a90	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

37703

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

41317

PDB ID

Not Available

ChEBI ID

50172

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 9-cis Acitretin (HMDB0247585)

MOL for HMDB0247585 (9-cis Acitretin)

3D MOL for HMDB0247585 (9-cis Acitretin)

3D SDF for HMDB0247585 (9-cis Acitretin)

3D-SDF for HMDB0247585 (9-cis Acitretin)

PDB for HMDB0247585 (9-cis Acitretin)

3D PDB for HMDB0247585 (9-cis Acitretin)

SMILES for HMDB0247585 (9-cis Acitretin)

INCHI for HMDB0247585 (9-cis Acitretin)

Structure for HMDB0247585 (9-cis Acitretin)

3D Structure for HMDB0247585 (9-cis Acitretin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra