T3DB: Icaridin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (7)XML

Targets (7)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:52 UTC

Update Date

2014-12-24 20:26:33 UTC

Accession Number

T3D3859

Identification

Common Name

Icaridin

Class

Small Molecule

Description

Icaridin, also known as picaridin, KBR 3023, under the INCI name hydroxyethyl isobutyl piperidine carboxylate, and the trade names Bayrepel and Saltidin, is an insect repellent. It has broad efficacy against different insects and is almost colorless and odorless.

Compound Type

Amine
Ester
Ether
Household Toxin
Insect Repellent
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-(1-Methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine
1-Methylpropyl 2-(2-hydroxyethyl)-1-piperidinecarboxylate
1-Methylpropyl 2-(2-hydroxyethyl)piperidine-1-carboxylate
Bayrepel
Cutter Advanced
Methylpropyl 2-(2-hydroxyethyl)piperidinecarboxylate
Picaridin
Propidine
sec-Butyl 2-(2-hydroxyethyl)-1-piperidinecarboxylate

Chemical Formula

C₁₂H₂₃NO₃

Average Molecular Mass

229.316 g/mol

Monoisotopic Mass

229.168 g/mol

CAS Registry Number

119515-38-7

IUPAC Name

butan-2-yl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Traditional Name

icaridin

SMILES

CCC(C)OC(=O)N1CCCCC1CCO

InChI Identifier

InChI=1S/C12H23NO3/c1-3-10(2)16-12(15)13-8-5-4-6-11(13)7-9-14/h10-11,14H,3-9H2,1-2H3

InChI Key

InChIKey=QLHULAHOXSSASE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxylic acids

Alternative Parents

Substituents

Piperidinecarboxylic acid
Carbamic acid ester
Carbonic acid derivative
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	25.1 g/L	ALOGPS
logP	2.19	ALOGPS
logP	1.61	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	15.92	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.54 m³·mol⁻¹	ChemAxon
Polarizability	26.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9710000000-df0e7cebfacfe49cb92b	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-001i-0900000000-58f1702d6f45aa777f96	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-5cef5dc711524ef3bd7f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-4038f3c5e4bfdaf32538	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-84fc35113c0426313f33	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-12396b24426a71c38be1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-53f3c51c337bee23b64f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-4f5cb36e92522cf58afa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-001i-0900000000-0b9182859c214da7e606	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00o0-0900000000-a1a14503fdf7d842458f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-8c17f06df0e54407dca0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-001i-1900000000-c043d43ea90c7dc975c2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-001i-0900000000-46e5423e2b1f9aa6a625	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00o0-0900000000-d86d9c4b63234864b6ec	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-06e9-9100000000-d5e323bf9496a7bab621	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-001j-5900000000-4a68dbf94a50d9208492	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-0d4e859962f2ef377815	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00si-9300000000-10e25ab0bf74159a2466	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-001i-7900000000-f37268309c628ceaa722	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06si-2950000000-36505610e4aa874d91b4	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-8900000000-930b890acdb962fdc88e	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bt9-9500000000-7fa289c2d7a8debee429	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-5980000000-61c3a48aef046b0e5a2a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmj-5920000000-7b1cb290f7bcb281d48a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kkc-8900000000-d8eedf690c9700bcb6e4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1890000000-683315a61d2715077005	2021-10-12	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

125098

ChEMBL ID

CHEMBL2104314

ChemSpider ID

111359

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Urokinase-type plasminogen activator

General Function:: Serine-type endopeptidase activity
Specific Function:: Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
Gene Name:: PLAU
Uniprot ID:: P00749
Molecular Weight:: 48507.09 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_BE3C_uPA_down	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

2. Cytochrome P450 2C9

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular Weight:: 55627.365 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.67 uM	CLZD_CYP2C9_6	CellzDirect

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

3. Cytochrome P450 2B6

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular Weight:: 56277.81 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.98 uM	CLZD_CYP2B6_6	CellzDirect
AC50	4.07 uM	CLZD_CYP2B6_24	CellzDirect

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

4. C-C motif chemokine 2

General Function:: Not Available
Specific Function:: Not Available
Gene Name:: CCL2
Uniprot ID:: P13500
Molecular Weight:: 11024.87 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_SM3C_MCP1_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

5. Interleukin-1 alpha

General Function:: Cytokine activity
Specific Function:: Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
Gene Name:: IL1A
Uniprot ID:: P01583
Molecular Weight:: 30606.29 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_BE3C_IL1a_up	BioSeek

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

6. Cytochrome P450 3A4

General Function:: Vitamin d3 25-hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular Weight:: 57342.67 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	6.82 uM	CLZD_CYP3A4_6	CellzDirect

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

7. Oxysterols receptor LXR-beta

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor. Binds preferentially to double-stranded oligonucleotide direct repeats having the consensus half-site sequence 5'-AGGTCA-3' and 4-nt spacing (DR-4). Regulates cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8; DLDLR and LRP8. Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Exhibits a ligand-dependent transcriptional activation activity (PubMed:25661920).
Gene Name:: NR1H2
Uniprot ID:: P55055
Molecular Weight:: 50973.375 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.00 uM	ATG_LXRb_TRANS	Attagene
AC50	6.99 uM	ATG_LXRb_TRANS	Attagene

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Icaridin (T3D3859)

Structure for T3D3859: Icaridin

Targets

Binding/Activity Constants

References

Binding/Activity Constants

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