ContaminantDB: Clobetasol

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

Record Information

Version

1.0

Creation Date

2016-05-22 06:52:13 UTC

Update Date

2016-11-09 01:16:09 UTC

Accession Number

CHEM020171

Identification

Common Name

Clobetasol

Class

Small Molecule

Description

A 3-oxo-Delta(1),Delta(4)-steroid that is 16beta-methylpregna-1,4-diene-3,20-dione bearing hydroxy groups at the 11beta and 17alpha positions, fluorine at position 9, and a chlorine substituent at position 21. It is used as its 17alpha-propionate ester to treat various skin disorders, including exzema and psoriasis.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11beta,16beta)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	ChEBI
Clobetasolum	ChEBI
Clobecort amex	Kegg
(11b,16b)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
(11Β,16β)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
Clobetasol 17 propionate	HMDB
Clobetasol 17-propionate	HMDB
Clobetasol propionate	HMDB
Clobex	HMDB
Clofenazon	HMDB
Cormax	HMDB
Dermovate	HMDB
Embeline	HMDB
Embeline e	HMDB
OLUX	HMDB
Temovate	HMDB

Chemical Formula

C₂₂H₂₈ClFO₄

Average Molecular Mass

410.907 g/mol

Monoisotopic Mass

410.166 g/mol

CAS Registry Number

25122-41-2

IUPAC Name

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

clobetasol

SMILES

[H][C@@]12C[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

InChI Key

FCSHDIVRCWTZOX-DVTGEIKXSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Hydroxysteroid
Halo-steroid
9-halo-steroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
Delta-1,4-steroid
Alpha-haloketone
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Alpha-chloroketone
Cyclic ketone
Secondary alcohol
Fluorohydrin
Halohydrin
Ketone
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl fluoride
Organofluoride
Organochloride
Organohalogen compound
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:205919 )
17alpha-hydroxy steroid (CHEBI:205919 )
glucocorticoid (CHEBI:205919 )
20-oxo steroid (CHEBI:205919 )
fluorinated steroid (CHEBI:205919 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:205919 )
chlorinated steroid (CHEBI:205919 )

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	0.014 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.04	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	41.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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	splash10-05ur-1922000000-1a2dff27fd4359dcf1ff	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-000l-3545390000-45a386f33671c09db1ef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0960000000-a22cd2cf411698d4cb20	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0009400000-e9436fb9bac8eda3bf10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00dj-0960000000-6443ffdb9b79ef387dc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-01w1-0692000000-4a54671d4895c5118cc1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-01w1-0692000000-ee83dc8cb91bcf54300f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-022a-0890000000-38b8d519ad2a9ba13b3d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0469000000-31fce0ad107cfd522ffc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0009400000-8d3f1a9dbe178961f1a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ec-0009300000-eabf4bbbde18aa470559	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06vl-0139100000-5851c4786f4f11dac8a4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0i6r-0396000000-ce80f2ae92c03b288ae7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0005900000-08f019701c8687b3adfa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05fr-1009200000-83699a43939ad9dd09a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gc0-1029000000-d3f4258d8f19313ca5a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0009700000-1851cdf5907155e33c20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-0869400000-ff98ebd4c04b608835cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-2891000000-106ece766a3163e1226b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-0009800000-d247e43fa37d759961e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1009000000-d289c7e30bdafdb38a90	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1019000000-0e4b816a146275aa7238	Spectrum