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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:06:06 UTC

Update Date

2019-07-23 07:14:43 UTC

HMDB ID

HMDB0060619

Secondary Accession Numbers

HMDB60619

Metabolite Identification

Common Name

Tazarotenic acid

Description

Tazarotenic acid is a metabolite of tazarotene. Tazarotene (marketed as Tazorac, Avage and Zorac) 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). It is commonly sold in two concentrations: 0.05% and 0.1%. Common side effects include worsening of acne, dry skin, itchiness, redness and in some cases extreme drying and cracking of skin. (Wikipedia)

Structure

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

HMDB0060619
     RDKit          3D
Tazarotenic acid
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.3329    0.6015    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116   -0.3782    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718   -1.4222    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -1.0870   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.1435   -0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477    1.4433   -1.2552 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844    1.1960   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    1.8533   -1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291    1.5890   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    0.6780   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    0.4009   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    0.1488   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -0.1680   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -0.1514   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8867   -0.4515   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -0.7767    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6842   -1.0977    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0772   -1.3967    1.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661   -1.1039   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -0.7983    1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.4943    1.1557 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    0.0321    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5650    0.2986   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    0.2176    2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    0.7368    1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339    1.5978    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3302   -0.9495    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.8929    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674   -2.1938    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2554   -1.6998    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.8089   -0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4871    0.0343   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -0.6235   -1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    2.5438   -2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    2.1009   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176    0.1055   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086   -0.4438   -1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7104   -0.4093   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084   -1.0505    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9104   -0.6683    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  3  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  2  0
 23  2  1  0
 23  7  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
M  END

  Mrv0541 06151311062D          

 23 25  0  0  0  0            999 V2000
    0.5303    0.6320    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
   -0.7145   -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
    0.0000   -1.6500    0.0000 S   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   -0.4125    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  3  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060619

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)

> <INCHI_KEY>
IQIBKLWBVJPOQO-UHFFFAOYSA-N

> <FORMULA>
C19H17NO2S

> <MOLECULAR_WEIGHT>
323.409

> <EXACT_MASS>
323.097999483

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.19599206108543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.516038541

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.762058177720765

> <JCHEM_PKA_STRONGEST_BASIC>
1.2302226886696461

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
88.3643

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[2-(4,4-dimethyl-2,3-dihydro-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060619
     RDKit          3D
Tazarotenic acid
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.3329    0.6015    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116   -0.3782    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718   -1.4222    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -1.0870   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.1435   -0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477    1.4433   -1.2552 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844    1.1960   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    1.8533   -1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291    1.5890   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    0.6780   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    0.4009   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    0.1488   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -0.1680   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -0.1514   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8867   -0.4515   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -0.7767    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6842   -1.0977    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0772   -1.3967    1.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661   -1.1039   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -0.7983    1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.4943    1.1557 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    0.0321    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5650    0.2986   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    0.2176    2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    0.7368    1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339    1.5978    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3302   -0.9495    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.8929    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674   -2.1938    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2554   -1.6998    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.8089   -0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4871    0.0343   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -0.6235   -1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    2.5438   -2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    2.1009   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176    0.1055   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086   -0.4438   -1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7104   -0.4093   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084   -1.0505    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9104   -0.6683    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  3  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  2  0
 23  2  1  0
 23  7  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.000  -3.080   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.002   3.080   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   23                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    2                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0060619
HETATM    1  C1  UNL     1      -4.333   0.602   1.576  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.612  -0.378   0.675  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.972  -1.422   1.581  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.626  -1.087  -0.172  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.550  -0.144  -0.907  1.00  0.00           C  
HETATM    6  S1  UNL     1      -4.748   1.443  -1.255  1.00  0.00           S  
HETATM    7  C6  UNL     1      -2.984   1.196  -1.091  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.059   1.853  -1.869  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.729   1.589  -1.660  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.306   0.678  -0.685  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.086   0.401  -0.466  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.252   0.149  -0.280  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.640  -0.168  -0.062  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.558  -0.151  -1.105  1.00  0.00           C  
HETATM   15  C14 UNL     1       5.887  -0.451  -0.913  1.00  0.00           C  
HETATM   16  C15 UNL     1       6.307  -0.777   0.355  1.00  0.00           C  
HETATM   17  C16 UNL     1       7.684  -1.098   0.606  1.00  0.00           C  
HETATM   18  O1  UNL     1       8.077  -1.397   1.765  1.00  0.00           O  
HETATM   19  O2  UNL     1       8.666  -1.104  -0.383  1.00  0.00           O  
HETATM   20  C17 UNL     1       5.404  -0.798   1.409  1.00  0.00           C  
HETATM   21  N1  UNL     1       4.114  -0.494   1.156  1.00  0.00           N  
HETATM   22  C18 UNL     1      -1.245   0.032   0.081  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.565   0.299  -0.132  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.418   0.218   2.617  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.386   0.737   1.226  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.834   1.598   1.583  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.330  -0.950   2.354  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.818  -1.893   2.141  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.467  -2.194   0.997  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.255  -1.700   0.508  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.145  -1.809  -0.869  1.00  0.00           H  
HETATM   32  H9  UNL     1      -6.487   0.034  -0.341  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.770  -0.623  -1.895  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.382   2.544  -2.607  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.012   2.101  -2.266  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.218   0.106  -2.098  1.00  0.00           H  
HETATM   37  H14 UNL     1       6.609  -0.444  -1.704  1.00  0.00           H  
HETATM   38  H15 UNL     1       8.710  -0.409  -1.114  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.708  -1.050   2.414  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.910  -0.668   0.829  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   23
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7
CONECT    7    8    8   23
CONECT    8    9   34
CONECT    9   10   10   35
CONECT   10   11   22
CONECT   11   12   12   12
CONECT   12   13
CONECT   13   14   14   21
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   20
CONECT   17   18   18   19
CONECT   19   38
CONECT   20   21   21   39
CONECT   22   23   23   40
END

HMDB0060619
     RDKit          3D
Tazarotenic acid
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.3329    0.6015    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116   -0.3782    0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9718   -1.4222    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -1.0870   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.1435   -0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7477    1.4433   -1.2552 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9844    1.1960   -1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595    1.8533   -1.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7291    1.5890   -1.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3061    0.6780   -0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    0.4009   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    0.1488   -0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6400   -0.1680   -0.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585   -0.1514   -1.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8867   -0.4515   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -0.7767    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6842   -1.0977    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0772   -1.3967    1.7652 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6661   -1.1039   -0.3826 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038   -0.7983    1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1142   -0.4943    1.1557 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    0.0321    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5650    0.2986   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    0.2176    2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    0.7368    1.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339    1.5978    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3302   -0.9495    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.8929    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674   -2.1938    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2554   -1.6998    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453   -1.8089   -0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4871    0.0343   -0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -0.6235   -1.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    2.5438   -2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    2.1009   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176    0.1055   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086   -0.4438   -1.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7104   -0.4093   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7084   -1.0505    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9104   -0.6683    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  3  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 10 22  1  0
 22 23  2  0
 23  2  1  0
 23  7  1  0
 21 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  8 34  1  0
  9 35  1  0
 14 36  1  0
 15 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-((3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-3-pyridinecarboxylic acid	ChEBI
AGN 190299	ChEBI
AGN-190299	ChEBI
6-((3,4-Dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-3-pyridinecarboxylate	Generator
Tazarotenate	Generator

Chemical Formula

C₁₉H₁₇NO₂S

Average Molecular Weight

323.409

Monoisotopic Molecular Weight

323.097999483

IUPAC Name

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

Traditional Name

6-[2-(4,4-dimethyl-2,3-dihydro-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C19H17NO2S/c1-19(2)9-10-23-17-8-4-13(11-16(17)19)3-6-15-7-5-14(12-20-15)18(21)22/h4-5,7-8,11-12H,9-10H2,1-2H3,(H,21,22)

InChI Key

IQIBKLWBVJPOQO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiochromanes. These are organic heterocyclic compounds containing a thiochromane moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiochromanes

Sub Class

Not Available

Direct Parent

Thiochromanes

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:73129 )
retinoid (CHEBI:73129 )
pyridines (CHEBI:73129 )
thiochromane (CHEBI:73129 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060619)

Organ

Kidney (HMDB: HMDB0060619)
Liver (HMDB: HMDB0060619)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060619)

Cellular substructure

Cytoplasm (HMDB: HMDB0060619)
Membrane (HMDB: HMDB0060619)

Source

Endogenous

Endogenous (HMDB: HMDB0060619)

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
Water Solubility	0.0012 g/L	ALOGPS
logP	4.59	ALOGPS
logP	4.52	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	1.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.36 m³·mol⁻¹	ChemAxon
Polarizability	36.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.452	31661259
DarkChem	[M-H]-	178.088	31661259
DeepCCS	[M+H]+	176.845	30932474
DeepCCS	[M-H]-	174.487	30932474
DeepCCS	[M-2H]-	207.373	30932474
DeepCCS	[M+Na]+	182.938	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	173.9	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.4	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	178.1	32859911
AllCCS	[M+HCOO]-	177.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tazarotenic acid	CC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O	4390.2	Standard polar	33892256
Tazarotenic acid	CC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O	2910.8	Standard non polar	33892256
Tazarotenic acid	CC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O	3209.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tazarotenic acid,1TMS,isomer #1	CC1(C)CCSC2=CC=C(C#CC3=CC=C(C(=O)O[Si](C)(C)C)C=N3)C=C21	3035.9	Semi standard non polar	33892256
Tazarotenic acid,1TBDMS,isomer #1	CC1(C)CCSC2=CC=C(C#CC3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=N3)C=C21	3284.6	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 - Tazarotenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1196000000-4bfef9e6f4d527e4e077	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tazarotenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9018000000-f8b6cd0482cf75f9dcfd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tazarotenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Positive-QTOF	splash10-05fr-0019000000-1ec2c1f469752afcc687	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Positive-QTOF	splash10-0a4i-8259000000-4fda633cf8fdc5e49856	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Positive-QTOF	splash10-0059-1390000000-8d837ce9675ef9ba042c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Negative-QTOF	splash10-00di-0039000000-ce9757dfa6a1f2c24f30	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Negative-QTOF	splash10-004i-0094000000-81ee4f140f27a86bd76b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Negative-QTOF	splash10-004i-5090000000-5841d9529ec11acee7bd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Positive-QTOF	splash10-00di-0009000000-6b9907032bd3fd9b7ae6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Positive-QTOF	splash10-05fr-1098000000-6737dc976e8d9c09d5bf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Positive-QTOF	splash10-0h6r-0291000000-f09f0de2adf4b8a7357e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Negative-QTOF	splash10-004i-0091000000-a75dc3b68bef4411cffa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Negative-QTOF	splash10-004i-0091000000-16a3029fafa6c57a4bf6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Negative-QTOF	splash10-004i-2090000000-3050bb4b3bd1b8a0e36d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

147525

PDB ID

Not Available

ChEBI ID

73129

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

Abramovits W, Abdelmalek N: Treatment of warty dyskeratoma with tazarotenic acid. J Am Acad Dermatol. 2002 Feb;46(2 Suppl Case Reports):S4. [PubMed:11807455 ]
Attar M, Dong D, Ling KH, Tang-Liu DD: Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. Drug Metab Dispos. 2003 Apr;31(4):476-81. [PubMed:12642475 ]

Showing metabocard for Tazarotenic acid (HMDB0060619)

MOL for HMDB0060619 (Tazarotenic acid)

3D MOL for HMDB0060619 (Tazarotenic acid)

3D SDF for HMDB0060619 (Tazarotenic acid)

3D-SDF for HMDB0060619 (Tazarotenic acid)

PDB for HMDB0060619 (Tazarotenic acid)

3D PDB for HMDB0060619 (Tazarotenic acid)

SMILES for HMDB0060619 (Tazarotenic acid)

INCHI for HMDB0060619 (Tazarotenic acid)

Structure for HMDB0060619 (Tazarotenic acid)

3D Structure for HMDB0060619 (Tazarotenic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra