T3DB: Fenhexamid

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 07:56:51 UTC

Update Date

2014-12-24 20:26:33 UTC

Accession Number

T3D3838

Identification

Common Name

Fenhexamid

Class

Small Molecule

Description

Fenhexamid is a locally systemic, protectant fungicide. Fenhexamid prevents fungi from infecting plants by inhibiting spore germination and mycelial growth. The fungicide is absorbed into the outer waxy layer of plant surfaces and is protected from being washed off by rainfall or irrigation. Used for control of Botrytis diseases on grapes, greenhouse tomatoes, ornamentals and berry crops, including blackberries, blueberries, currants, loganberries, raspberries and strawberries; and Monilinia brown rot on cherries, peaches and nectarines.

Compound Type

Amide
Amine
Fungicide
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Decree
Elevate
Fenhexamide
N-(2,3-Dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide
Teldor

Chemical Formula

C₁₄H₁₇Cl₂NO₂

Average Molecular Mass

302.196 g/mol

Monoisotopic Mass

301.064 g/mol

CAS Registry Number

126833-17-8

IUPAC Name

N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexane-1-carboxamide

Traditional Name

fenhexamid

SMILES

CC1(CCCCC1)C(=O)NC1=C(Cl)C(Cl)=C(O)C=C1

InChI Identifier

InChI=1S/C14H17Cl2NO2/c1-14(7-3-2-4-8-14)13(19)17-9-5-6-10(18)12(16)11(9)15/h5-6,18H,2-4,7-8H2,1H3,(H,17,19)

InChI Key

InChIKey=VDLGAVXLJYLFDH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
1,2-dichlorobenzene
3-halophenol
2-halophenol
3-chlorophenol
2-chlorophenol
N-arylamide
Chlorobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl halide
Aryl chloride
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:81853 )
phenols (CHEBI:81853 )
dichlorobenzene (CHEBI:81853 )
aromatic amide (CHEBI:81853 )
anilide fungicide (CHEBI:81853 )
Amide fungicides (C18593 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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	0.012 g/L	ALOGPS
logP	5.39	ALOGPS
logP	4.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.21 m³·mol⁻¹	ChemAxon
Polarizability	30.53 Å³	ChemAxon
Number of Rings	2	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	Not Available	2020-08-04	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 (TMS_1_2) - 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 9V, positive	splash10-0udi-0009000000-a0221ceb0f6408135342	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 18V, positive	splash10-0udi-2009000000-5ca632e131ff4102c86a	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 27V, positive	splash10-0002-9101000000-86f58bd795207d7b946c	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 36V, positive	splash10-0002-9100000000-0177447a40be2e61659f	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 45V, positive	splash10-0002-9100000000-b25d2948f9f280cf47b9	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 54V, positive	splash10-0a4j-9200000000-05240ecc8d0960cbc70f	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 9V, negative	splash10-0udi-0019000000-993b9c46bf4267789476	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 18V, negative	splash10-0ik9-0095000000-298c2d6f4d52edea34a4	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 27V, negative	splash10-03di-0090000000-9561a2d856296ed50b97	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 36V, negative	splash10-03dj-0190000000-5ac80e42f89cc9a18d3e	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 45V, negative	splash10-006t-0490000000-91fae1a00ef8046f3af6	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 54V, negative	splash10-00dm-0790000000-40c417e731fadce3bb94	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-9100000000-0177447a40be2e61659f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-9100000000-b25d2948f9f280cf47b9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0udi-0019000000-993b9c46bf4267789476	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a4j-9200000000-05240ecc8d0960cbc70f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-03dj-0190000000-5ac80e42f89cc9a18d3e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-006t-0490000000-91fae1a00ef8046f3af6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-03di-0090000000-9561a2d856296ed50b97	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1319000000-67a50fb634183842872c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3922000000-23f762d9dc3f7c0dadd8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9200000000-4271ee05a18e446d5177	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-ce76f4d5f98393dfc2cd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-3359000000-23786371c860ebc40b18	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fgd-6920000000-9d2151c7003a514d1f23	2016-08-03	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

This is a man-made compound that is used as a pesticide.

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

ChEMBL ID

ChemSpider ID

KEGG ID

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

T3D3838.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Nuclear receptor subfamily 1 group I member 2

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.91 uM	ATG_PXRE_CIS	Attagene
AC50	1.20 uM	NVS_NR_hPXR	Novascreen

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. Androgen receptor

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Molecular Weight:: 98987.9 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.71 uM	NVS_NR_hAR	Novascreen

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. Translocator protein

General Function:: Cholesterol binding
Specific Function:: Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular Weight:: 18827.81 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.74 uM	NVS_MP_hPBR	Novascreen

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. 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	2.50 uM	NVS_ADME_hCYP2C9	Novascreen

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. Substance-K receptor

General Function:: Tachykinin receptor activity
Specific Function:: This is a receptor for the tachykinin neuropeptide substance K (neurokinin A). It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: substance K > neuromedin-K > substance P.
Gene Name:: TACR2
Uniprot ID:: P21452
Molecular Weight:: 44441.705 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.15 uM	NVS_GPCR_hNK2	Novascreen

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 2C19

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular Weight:: 55930.545 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	5.86 uM	NVS_ADME_hCYP2C19	Novascreen

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. Sodium-dependent dopamine transporter

General Function:: Monoamine transmembrane transporter activity
Specific Function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular Weight:: 68494.255 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	6.00 uM	NVS_TR_hDAT	Novascreen

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 ]

Fenhexamid (T3D3838)

Structure for T3D3838: Fenhexamid

Targets

Binding/Activity Constants

References

Binding/Activity Constants

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Binding/Activity Constants

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