Paclobutrazol (CHEM002858)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2013-04-25 07:56:53 UTC
Update Date2016-11-09 01:08:59 UTC
Accession NumberCHEM002858
Identification
Common NamePaclobutrazol
ClassSmall Molecule
DescriptionPaclobutrazol (PBZ) is a plant growth retardant and triazole fungicide. It is a known antagonist of the plant hormone gibberellin. It acts by inhibiting gibberellin biosynthesis, reducing internodial growth to give stouter stems, increasing root growth, causing early fruitset and increasing seedset in plants such as tomato and pepper. PBZ has also been shown to reduce frost sensitivity in plants.
Contaminant Sources
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Fungicide
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3S)-PaclobutrazolChEBI
Caswell no. 628CChEBI
Paclobutrazol, (S-(r*,r*))-isomerMeSH
Paclobutrazol, (S-(r*,s*))-isomerMeSH
Paclobutrazol, (r*,s*)-(+-)-isomerMeSH
Paclobutrazol, (r*,s*)-isomerMeSH
Paclobutrazol, (R-(r*,r*))-isomerMeSH
1-(4-Chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-olMeSH
Paclobutrazol, (R-(r*,s*))-isomerMeSH
Chemical FormulaC15H20ClN3O
Average Molecular Mass293.792 g/mol
Monoisotopic Mass293.129 g/mol
CAS Registry Number76738-62-0
IUPAC Name(2S,3S)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol
Traditional Namepaclobutrazol
SMILESCC(C)(C)[C@H](O)[C@H](CC1=CC=C(Cl)C=C1)N1C=NC=N1
InChI IdentifierInChI=1S/C15H20ClN3O/c1-15(2,3)14(20)13(19-10-17-9-18-19)8-11-4-6-12(16)7-5-11/h4-7,9-10,13-14,20H,8H2,1-3H3/t13-,14+/m0/s1
InChI KeyRMOGWMIKYWRTKW-UONOGXRCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Azole
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP3.2ALOGPS
logP3.38ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)2.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.94 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.08 m³·mol⁻¹ChemAxon
Polarizability30.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-5ce48c193996bc98d2faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-1190000000-9850d1a5949766bc17d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9210000000-a8ded6cca7d8e4559a94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2090000000-c11a48c01ca1fe219b3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014l-6190000000-42cd6d36482e669d61f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-0621d6e7c2bd14447410Spectrum
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/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPaclobutrazol
Chemspider IDNot Available
ChEBI ID139344
PubChem Compound ID73671
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25820472