Tridemorph (T3D4939)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 05:23:17 UTC
Update Date2014-12-24 20:27:00 UTC
Accession NumberT3D4939
Identification
Common NameTridemorph
ClassSmall Molecule
DescriptionSystemic eradicant cereal fungicide Tridemorph is a fungicide. It was developed in the 1960s by the German multinational BASF who sell tridemorph under the trade name Calixin. It is used to control the fungus Erysiphe graminis in cereals, Mycosphaerella species in bananas, and Caticum solmonicolor in tea. Tridemorph is applied onto many crops across the world, but very little data on usage and production is in the public domain. In high doses it has been shown to have teratogenic effects. These effect are manifested in edemas, hemorrhages, hematomas, abnormal development of the brain (hydrocephalia), visceral cranium (micrognathia, cleft palate) and genitourinary system (hydronephrosis), in decreased size of pelvic bones, shoulder girdle, front and hind limbs, etc. (1) Tridemorph belongs to the family of Oxazinanes. These are compounds containing an oxazinane moiety, which consists of a saturated aliphatic six-member ring with one oxygen atom, a nitrogen atom, and four carbon atoms. Isomers of oxaphospholane include 1,2-oxazinane, 1,3-oxazinane, and 1,4-oxazinane.
Compound Type
  • Amine
  • Ether
  • Food Toxin
  • Fungicide
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2,6-Dimethyl-4-tridecyl-Morpholine
2,6-Dimethyl-4-tridecylmorpholine
2,6-Dimethyl-N-tridecyl-Morpholine
4-Tridecyl-2,6-dimethylmorpholine
BASF 220F
Calixin
Calixine
Dimethyl-2,6 tridecyl-4 morpholine
Elbamorph
F 220 (Fungicide)
Kalinin
Kalixin
N-Tridecyl-2,6-dimethylmorpholin
N-Tridecyl-2,6-dimethylmorpholine
Tridemorf
Tridemorphe
Chemical FormulaC19H39NO
Average Molecular Mass297.519 g/mol
Monoisotopic Mass297.303 g/mol
CAS Registry Number81412-43-3
IUPAC Name2,6-dimethyl-4-tridecylmorpholine
Traditional Namekalinin
SMILESCCCCCCCCCCCCCN1CC(C)OC(C)C1
InChI IdentifierInChI=1/C19H39NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-20-16-18(2)21-19(3)17-20/h18-19H,4-17H2,1-3H3
InChI KeyInChIKey=YTOPFCCWCSOHFV-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentMorpholines
Alternative Parents
Substituents
  • Morpholine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< 25 °C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP6.99ALOGPS
logP6.13ChemAxon
logS-6.4ALOGPS
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity93.18 m³·mol⁻¹ChemAxon
Polarizability40.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-020r-8970000000-10ddc835f5b043e257a52017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-9799a4d8461c70fcefaf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4890000000-6a7563ffc760f54b0da52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06xx-9510000000-20032a1ff46485ee571d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-afb4a1229961744221822016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0190000000-8ce67e1903c8e68971462016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9210000000-7ddceee3114005204dd52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-3ff27e40279a314542322021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1190000000-72908d7029f76602ff902021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-bdc65245b716d04247202021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-ca0fb58a7685fc0b781c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-aecc7081991bde11bad42021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-5970000000-0e0587eadcf6f9c6e9e82021-09-22View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB31810
PubChem Compound ID32518
ChEMBL IDNot Available
ChemSpider ID30142
KEGG IDC11285
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D4939.pdf
General References
  1. Shtenberg AI, Zaeva GN, Rysina TZ, Gavrilenko EV: [Teratogenic effect of the fungicide calixin]. Vopr Pitan. 1981 Nov-Dec;(6):55-61. [7324433 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot 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
TypeValueAssay TypeAssay Source
AC508.28 uMATG_PXRE_CISAttagene
References
  1. 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 ]