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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014937

Secondary Accession Numbers

HMDB14937

Metabolite Identification

Common Name

Tazarotene

Description

Tazarotene is only found in individuals that have used or taken this drug. It is a prescription topical retinoid sold as a cream or gel. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). [Wikipedia ]Although the exact mechanism of tazarotene action is not known, studies have shown that the active form of the drug (tazarotenic acid) binds to all three members of the retinoic acid receptor (RAR) family: RARa, RARb, and RARg, but shows relative selectivity for RARb, and RARg and may modify gene expression. It also has affinity for RXR receptors.

Structure

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

HMDB0014937
     RDKit          3D
Tazarotene
 46 48  0  0  0  0  0  0  0  0999 V2000
    9.1695    0.7798   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3644    1.6920    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9767    1.4614    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    0.2588    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1095   -0.6793    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.0322    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284   -1.1957    0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.4206    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828   -0.4301    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.6962    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179   -0.9262   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -1.2112   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365   -2.5040   -0.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.7741   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -1.7681   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408   -0.4857   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7668   -0.2409    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0297    0.6456    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9913    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4180    1.8588   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    0.5080   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1162   -0.7445    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -2.1463   -0.5764 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210    0.7685   -0.1674 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    1.0016   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8468    0.8424   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1447   -0.2521   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2273    1.1133   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7440    1.5386    1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5558    2.7466   -0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606   -2.0201    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174   -2.3770    0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -3.3032   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -3.7549   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3937    0.7529    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9145    1.5023    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.0752    2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122    1.6726    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    2.3988    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966    1.4977   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073    2.5062   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583    0.5297   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0114    1.3653    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1379   -0.7305   -0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0783   -0.8591    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.9802   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  9 24  1  0
 24 25  2  0
 25  6  1  0
 17 12  1  0
 23 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

799
  Mrv0541 02231215012D          

 25 27  0  0  0  0            999 V2000
    2.3645    2.2713    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5574   -1.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8381   -2.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995   -1.0541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    0.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8165    2.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769    0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187    0.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1284   -1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1316   -0.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4124   -1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8413   -1.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2702   -1.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9863   -1.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2 23  1  0  0  0  0
  2 24  1  0  0  0  0
  3 23  2  0  0  0  0
  4 18  2  0  0  0  0
  4 22  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  3  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014937

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3

> <INCHI_KEY>
OGQICQVSFDPSEI-UHFFFAOYSA-N

> <FORMULA>
C21H21NO2S

> <MOLECULAR_WEIGHT>
351.462

> <EXACT_MASS>
351.129299611

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.31083826690598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
5.218740551666667

> <ALOGPS_LOGS>
-5.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.2257417412293548

> <JCHEM_POLAR_SURFACE_AREA>
39.19

> <JCHEM_REFRACTIVITY>
97.88199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tazarotene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014937
     RDKit          3D
Tazarotene
 46 48  0  0  0  0  0  0  0  0999 V2000
    9.1695    0.7798   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3644    1.6920    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9767    1.4614    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    0.2588    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1095   -0.6793    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.0322    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284   -1.1957    0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.4206    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828   -0.4301    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.6962    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179   -0.9262   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -1.2112   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365   -2.5040   -0.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.7741   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -1.7681   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408   -0.4857   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7668   -0.2409    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0297    0.6456    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9913    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4180    1.8588   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    0.5080   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1162   -0.7445    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -2.1463   -0.5764 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210    0.7685   -0.1674 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    1.0016   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8468    0.8424   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1447   -0.2521   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2273    1.1133   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7440    1.5386    1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5558    2.7466   -0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606   -2.0201    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174   -2.3770    0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -3.3032   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -3.7549   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3937    0.7529    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9145    1.5023    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.0752    2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122    1.6726    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    2.3988    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966    1.4977   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073    2.5062   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583    0.5297   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0114    1.3653    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1379   -0.7305   -0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0783   -0.8591    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.9802   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  9 24  1  0
 24 25  2  0
 25  6  1  0
 17 12  1  0
 23 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 799                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.414   4.240   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      17.840  -1.988   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.498  -4.293   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      12.506  -1.968   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.414   1.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.080   1.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   1.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644  -0.174   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.174   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   3.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747   3.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.124   1.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.124   4.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.519   1.898   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.519   3.502   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.850   1.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.181   0.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.512  -0.428   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.848   0.337   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.173  -1.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.179  -0.438   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.836  -2.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.504  -2.753   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.171  -2.763   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.508  -1.999   0.000  0.00  0.00           C+0
CONECT    1   10   11                                                       
CONECT    2   23   24                                                       
CONECT    3   23                                                            
CONECT    4   18   22                                                       
CONECT    5    6    7    8    9                                             
CONECT    6    5   10                                                       
CONECT    7    5   11   12                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    1    6                                                       
CONECT   11    1    7   13                                                  
CONECT   12    7   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15   16                                                  
CONECT   15   13   14                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18    4   17   19                                                  
CONECT   19   18   21                                                       
CONECT   20   21   22   23                                                  
CONECT   21   19   20                                                       
CONECT   22    4   20                                                       
CONECT   23    2    3   20                                                  
CONECT   24    2   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014937
HETATM    1  C1  UNL     1       9.170   0.780  -0.660  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.364   1.692   0.222  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.977   1.461   0.128  1.00  0.00           O  
HETATM    4  C3  UNL     1       6.370   0.259   0.431  1.00  0.00           C  
HETATM    5  O2  UNL     1       7.110  -0.679   0.814  1.00  0.00           O  
HETATM    6  C4  UNL     1       4.942   0.032   0.330  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.428  -1.196   0.653  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.061  -1.421   0.559  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.183  -0.430   0.143  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.775  -0.696   0.057  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.418  -0.926  -0.035  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.820  -1.211  -0.163  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.237  -2.504  -0.499  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.582  -2.774  -0.621  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.488  -1.768  -0.411  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.141  -0.486  -0.080  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.767  -0.241   0.037  1.00  0.00           C  
HETATM   18  C16 UNL     1      -5.030   0.646   0.162  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.966   0.991   1.651  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.418   1.859  -0.553  1.00  0.00           C  
HETATM   21  C19 UNL     1      -6.421   0.508  -0.328  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.116  -0.745   0.157  1.00  0.00           C  
HETATM   23  S1  UNL     1      -6.226  -2.146  -0.576  1.00  0.00           S  
HETATM   24  N1  UNL     1       2.721   0.768  -0.167  1.00  0.00           N  
HETATM   25  C21 UNL     1       4.052   1.002  -0.080  1.00  0.00           C  
HETATM   26  H1  UNL     1       8.847   0.842  -1.724  1.00  0.00           H  
HETATM   27  H2  UNL     1       9.145  -0.252  -0.262  1.00  0.00           H  
HETATM   28  H3  UNL     1      10.227   1.113  -0.598  1.00  0.00           H  
HETATM   29  H4  UNL     1       8.744   1.539   1.269  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.556   2.747  -0.022  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.061  -2.020   0.987  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.617  -2.377   0.805  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.543  -3.303  -0.667  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.939  -3.755  -0.878  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.394   0.753   0.297  1.00  0.00           H  
HETATM   36  H11 UNL     1      -5.914   1.502   1.907  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.843   0.075   2.264  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.112   1.673   1.840  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.729   2.399   0.119  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.797   1.498  -1.415  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.207   2.506  -0.957  1.00  0.00           H  
HETATM   42  H17 UNL     1      -6.458   0.530  -1.418  1.00  0.00           H  
HETATM   43  H18 UNL     1      -7.011   1.365   0.077  1.00  0.00           H  
HETATM   44  H19 UNL     1      -8.138  -0.731  -0.255  1.00  0.00           H  
HETATM   45  H20 UNL     1      -7.078  -0.859   1.254  1.00  0.00           H  
HETATM   46  H21 UNL     1       4.445   1.980  -0.339  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   25
CONECT    7    8   31
CONECT    8    9    9   32
CONECT    9   10   24
CONECT   10   11   11   11
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16   23
CONECT   16   17   17   18
CONECT   17   35
CONECT   18   19   20   21
CONECT   19   36   37   38
CONECT   20   39   40   41
CONECT   21   22   42   43
CONECT   22   23   44   45
CONECT   24   25   25
CONECT   25   46
END

HMDB0014937
     RDKit          3D
Tazarotene
 46 48  0  0  0  0  0  0  0  0999 V2000
    9.1695    0.7798   -0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3644    1.6920    0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9767    1.4614    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3702    0.2588    0.4312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1095   -0.6793    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9420    0.0322    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4284   -1.1957    0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.4206    0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1828   -0.4301    0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7746   -0.6962    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179   -0.9262   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8202   -1.2112   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365   -2.5040   -0.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5815   -2.7741   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4880   -1.7681   -0.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1408   -0.4857   -0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7668   -0.2409    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0297    0.6456    0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9663    0.9913    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4180    1.8588   -0.5533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    0.5080   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1162   -0.7445    0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2263   -2.1463   -0.5764 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210    0.7685   -0.1674 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518    1.0016   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8468    0.8424   -1.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1447   -0.2521   -0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2273    1.1133   -0.5976 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7440    1.5386    1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5558    2.7466   -0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606   -2.0201    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174   -2.3770    0.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -3.3032   -0.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -3.7549   -0.8777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3937    0.7529    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9145    1.5023    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8429    0.0752    2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1122    1.6726    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    2.3988    0.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966    1.4977   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2073    2.5062   -0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4583    0.5297   -1.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0114    1.3653    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1379   -0.7305   -0.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0783   -0.8591    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449    1.9802   -0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  3  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  9 24  1  0
 24 25  2  0
 25  6  1  0
 17 12  1  0
 23 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  7 31  1  0
  8 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 20 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 25 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Avage	ChEBI
Tazaroteno	ChEBI
Tazarotenum	ChEBI
Tazorac	ChEBI
Zorac	ChEBI
Fabior	Kegg

Chemical Formula

C₂₁H₂₁NO₂S

Average Molecular Weight

351.462

Monoisotopic Molecular Weight

351.129299611

IUPAC Name

ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate

Traditional Name

tazarotene

CAS Registry Number

118292-40-3

SMILES

CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1

InChI Identifier

InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3

InChI Key

OGQICQVSFDPSEI-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

Tazarotene
Thiochromane
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Benzothiopyran
1-benzothiopyran
Aryl thioether
Alkylarylthioether
Pyridine
Thiopyran
Benzenoid
Heteroaromatic compound
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Thioether
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ethyl ester (CHEBI:32184 )
retinoid (CHEBI:32184 )
pyridines (CHEBI:32184 )
acetylenic compound (CHEBI:32184 )
thiochromane (CHEBI:32184 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00075 g/L	Not Available
LogP	5.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00075 g/L	ALOGPS
logP	5.15	ALOGPS
logP	5.22	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	1.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.19 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.88 m³·mol⁻¹	ChemAxon
Polarizability	40.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.728	31661259
DarkChem	[M-H]-	187.848	31661259
DeepCCS	[M+H]+	183.926	30932474
DeepCCS	[M-H]-	181.568	30932474
DeepCCS	[M-2H]-	215.754	30932474
DeepCCS	[M+Na]+	190.981	30932474
AllCCS	[M+H]+	186.0	32859911
AllCCS	[M+H-H2O]+	182.9	32859911
AllCCS	[M+NH4]+	188.9	32859911
AllCCS	[M+Na]+	189.7	32859911
AllCCS	[M-H]-	186.9	32859911
AllCCS	[M+Na-2H]-	186.7	32859911
AllCCS	[M+HCOO]-	186.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tazarotene	CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1	4327.5	Standard polar	33892256
Tazarotene	CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1	2978.2	Standard non polar	33892256
Tazarotene	CCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1	3235.9	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 - Tazarotene GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5059000000-5dfdf4638fc629294fd7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tazarotene 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 - Tazarotene LC-ESI-qTof , Positive-QTOF	splash10-0udi-1590000000-a511655f5e07f3ab2179	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tazarotene , positive-QTOF	splash10-0uk9-0129000000-2db71aa7cf68c539db6d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 10V, Positive-QTOF	splash10-0udi-0009000000-72f9d63158d045736501	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 20V, Positive-QTOF	splash10-0pb9-5439000000-3f943199dee72abc55c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 40V, Positive-QTOF	splash10-056s-3392000000-396babafcb01632299a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 10V, Negative-QTOF	splash10-0udi-0019000000-4cc7d0367627910edc39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 20V, Negative-QTOF	splash10-0udi-2039000000-83fa4db6d6d4f8c813ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 40V, Negative-QTOF	splash10-004i-5093000000-acd348facabd958ebaae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 10V, Positive-QTOF	splash10-0udi-0009000000-c9f64427c199d6d00c50	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 20V, Positive-QTOF	splash10-0ab9-0009000000-50dae41cf3fd9aca5f7f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 40V, Positive-QTOF	splash10-0lfr-0391000000-efdadade0fc0c9f5b093	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 10V, Negative-QTOF	splash10-0udi-0009000000-085c255d17aa534d26de	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 20V, Negative-QTOF	splash10-0udi-0019000000-d4c78dc93ef4adcb2fff	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotene 40V, Negative-QTOF	splash10-004i-1193000000-201b838185adb6fb2e67	2021-10-11	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 DB00799	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00799	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00799

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5188

KEGG Compound ID

C12531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tazarotene

METLIN ID

Not Available

PubChem Compound

5381

PDB ID

Not Available

ChEBI ID

32184

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. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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

2. 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 ]
Arechalde A, Saurat JH: Management of psoriasis: the position of retinoid drugs. BioDrugs. 2000 May;13(5):327-33. [PubMed:18034539 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. 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

Baumann L, Vujevich J, Halem M, Martin LK, Kerdel F, Lazarus M, Pacheco H, Black L, Bryde J: Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. Cutis. 2005 Jul;76(1):69-73. [PubMed:16144296 ]
Chandraratna RA: Tazarotene--first of a new generation of receptor-selective retinoids. Br J Dermatol. 1996 Oct;135 Suppl 49:18-25. [PubMed:9035701 ]
Yen A, Fenning R, Chandraratna R, Walker P, Varvayanis S: A retinoic acid receptor beta/gamma-selective prodrug (tazarotene) plus a retinoid X receptor ligand induces extracellular signal-regulated kinase activation, retinoblastoma hypophosphorylation, G0 arrest, and cell differentiation. Mol Pharmacol. 2004 Dec;66(6):1727-37. Epub 2004 Sep 21. [PubMed:15383624 ]
Meder W, Wendland M, Busmann A, Kutzleb C, Spodsberg N, John H, Richter R, Schleuder D, Meyer M, Forssmann WG: Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. FEBS Lett. 2003 Dec 18;555(3):495-9. [PubMed:14675762 ]
Wang Q, Lee D, Sysounthone V, Chandraratna RAS, Christakos S, Korah R, Wieder R: 1,25-dihydroxyvitamin D3 and retonic acid analogues induce differentiation in breast cancer cells with function- and cell-specific additive effects. Breast Cancer Res Treat. 2001 May;67(2):157-68. [PubMed:11519864 ]
Nagpal S, Chandraratna RA: Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31. [PubMed:10828316 ]

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

Jones PH, Burnett RD, Fainaru I, Nadolny P, Walker P, Yu Z, Tang-Liu D, Ganesan TS, Talbot DC, Harris AL, Rustin GJ: A phase 1 study of tazarotene in adults with advanced cancer. Br J Cancer. 2003 Sep 1;89(5):808-15. [PubMed:12942109 ]
Orlandi A, Bianchi L, Costanzo A, Campione E, Giusto Spagnoli L, Chimenti S: Evidence of increased apoptosis and reduced proliferation in basal cell carcinomas treated with tazarotene. J Invest Dermatol. 2004 Apr;122(4):1037-41. [PubMed:15102095 ]
Chandraratna RA: Tazarotene--first of a new generation of receptor-selective retinoids. Br J Dermatol. 1996 Oct;135 Suppl 49:18-25. [PubMed:9035701 ]
Arechalde A, Saurat JH: Management of psoriasis: the position of retinoid drugs. BioDrugs. 2000 May;13(5):327-33. [PubMed:18034539 ]

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 ]
Nagpal S, Chandraratna RA: Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31. [PubMed:10828316 ]

Showing metabocard for Tazarotene (HMDB0014937)

MOL for HMDB0014937 (Tazarotene)

3D MOL for HMDB0014937 (Tazarotene)

3D SDF for HMDB0014937 (Tazarotene)

3D-SDF for HMDB0014937 (Tazarotene)

PDB for HMDB0014937 (Tazarotene)

3D PDB for HMDB0014937 (Tazarotene)

SMILES for HMDB0014937 (Tazarotene)

INCHI for HMDB0014937 (Tazarotene)

Structure for HMDB0014937 (Tazarotene)

3D Structure for HMDB0014937 (Tazarotene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References