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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:06:06 UTC
Update Date2019-07-23 07:14:43 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
Data?1563866083
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
Description 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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.45231661259
DarkChem[M-H]-178.08831661259
DeepCCS[M+H]+176.84530932474
DeepCCS[M-H]-174.48730932474
DeepCCS[M-2H]-207.37330932474
DeepCCS[M+Na]+182.93830932474
AllCCS[M+H]+177.332859911
AllCCS[M+H-H2O]+173.932859911
AllCCS[M+NH4]+180.532859911
AllCCS[M+Na]+181.432859911
AllCCS[M-H]-178.632859911
AllCCS[M+Na-2H]-178.132859911
AllCCS[M+HCOO]-177.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tazarotenic acidCC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O4390.2Standard polar33892256
Tazarotenic acidCC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O2910.8Standard non polar33892256
Tazarotenic acidCC1(C)CCSC2=C1C=C(C=C2)C#CC1=NC=C(C=C1)C(O)=O3209.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tazarotenic acid,1TMS,isomer #1CC1(C)CCSC2=CC=C(C#CC3=CC=C(C(=O)O[Si](C)(C)C)C=N3)C=C213035.9Semi standard non polar33892256
Tazarotenic acid,1TBDMS,isomer #1CC1(C)CCSC2=CC=C(C#CC3=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=N3)C=C213284.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tazarotenic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1196000000-4bfef9e6f4d527e4e0772017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tazarotenic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9018000000-f8b6cd0482cf75f9dcfd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tazarotenic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Positive-QTOFsplash10-05fr-0019000000-1ec2c1f469752afcc6872017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Positive-QTOFsplash10-0a4i-8259000000-4fda633cf8fdc5e498562017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Positive-QTOFsplash10-0059-1390000000-8d837ce9675ef9ba042c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Negative-QTOFsplash10-00di-0039000000-ce9757dfa6a1f2c24f302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Negative-QTOFsplash10-004i-0094000000-81ee4f140f27a86bd76b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Negative-QTOFsplash10-004i-5090000000-5841d9529ec11acee7bd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Positive-QTOFsplash10-00di-0009000000-6b9907032bd3fd9b7ae62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Positive-QTOFsplash10-05fr-1098000000-6737dc976e8d9c09d5bf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Positive-QTOFsplash10-0h6r-0291000000-f09f0de2adf4b8a7357e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 10V, Negative-QTOFsplash10-004i-0091000000-a75dc3b68bef4411cffa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 20V, Negative-QTOFsplash10-004i-0091000000-16a3029fafa6c57a4bf62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tazarotenic acid 40V, Negative-QTOFsplash10-004i-2090000000-3050bb4b3bd1b8a0e36d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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 Compound147525
PDB IDNot Available
ChEBI ID73129
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]