ContaminantDB: Tazarotene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:53:07 UTC

Update Date

2016-10-28 10:03:22 UTC

Accession Number

CHEM019179

Identification

Common Name

Tazarotene

Class

Small Molecule

Description

Tazarotene, commonly marketed as Tazorac®, Avage®, and Zorac®, is member of the acetylenic class of retinoids. It is a prodrug that is found in topical formulations used in the treatment of various conditons, such as psoriasis, acne, and sun damaged skin (photodamage).

Contaminant Sources

Cosmetic Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₂₁H₂₁NO₂S

Average Molecular Mass

351.462 g/mol

Monoisotopic Mass

351.129 g/mol

CAS Registry Number

118292-40-3

IUPAC Name

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

Traditional Name

tazarotene

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted 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	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5059000000-5dfdf4638fc629294fd7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-1590000000-a511655f5e07f3ab2179	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0uk9-0129000000-2db71aa7cf68c539db6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-72f9d63158d045736501	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-5439000000-3f943199dee72abc55c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056s-3392000000-396babafcb01632299a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-4cc7d0367627910edc39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2039000000-83fa4db6d6d4f8c813ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-5093000000-acd348facabd958ebaae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-c9f64427c199d6d00c50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-0009000000-50dae41cf3fd9aca5f7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lfr-0391000000-efdadade0fc0c9f5b093	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-085c255d17aa534d26de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0019000000-d4c78dc93ef4adcb2fff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1193000000-201b838185adb6fb2e67	Spectrum