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Record Information
Version3.6
Creation Date2013-06-15 18:06:06 UTC
Update Date2016-02-11 08:09:27 UTC
HMDB IDHMDB60619
Secondary Accession NumbersNone
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 KeyInChIKey=IQIBKLWBVJPOQO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiochromanes. These are organic heterocyclic compounds containing a thiochromane moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiochromanes
Sub ClassNot Available
Direct ParentThiochromanes
Alternative Parents
Substituents
  • Thiochromane
  • Pyridine carboxylic acid or derivatives
  • Pyridine carboxylic acid
  • Alkylarylthioether
  • Benzenoid
  • Thiopyran
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.36 m3·mol-1ChemAxon
Polarizability36.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB60619
Metagene LinkHMDB60619
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID73129
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available