You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:06:06 UTC
Update Date2017-12-07 17:28:02 UTC
HMDB IDHMDB0060619
Secondary Accession Numbers
  • HMDB60619
Metabolite Identification
Common NameTazarotenic acid
DescriptionTazarotenic 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
Thumb
Synonyms
ValueSource
6-((3,4-dihydro-4,4-Dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-3-pyridinecarboxylic acidChEBI
AGN 190299ChEBI
AGN-190299ChEBI
6-((3,4-dihydro-4,4-Dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-3-pyridinecarboxylateGenerator
TazarotenateGenerator
Chemical FormulaC19H17NO2S
Average Molecular Weight323.409
Monoisotopic Molecular Weight323.097999483
IUPAC Name6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid
Traditional Name6-[2-(4,4-dimethyl-2,3-dihydro-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylic acid
CAS Registry NumberNot 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 KeyIQIBKLWBVJPOQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as thiochromanes. These are organic heterocyclic compounds containing a thiochromane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassThiochromanes
Direct ParentThiochromanes
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0012 g/LALOGPS
logP4.59ALOGPS
logP4.52ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)1.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.36 m³·mol⁻¹ChemAxon
Polarizability36.2 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1196000000-4bfef9e6f4d527e4e077View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9018000000-f8b6cd0482cf75f9dcfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0019000000-1ec2c1f469752afcc687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-8259000000-4fda633cf8fdc5e49856View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-1390000000-8d837ce9675ef9ba042cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0039000000-ce9757dfa6a1f2c24f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0094000000-81ee4f140f27a86bd76bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-5090000000-5841d9529ec11acee7bdView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET01005
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI ID73129
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. 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 ]
      2. 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 ]