Benthiavalicarb-isopropyl

Basic Info

Common NameBenthiavalicarb-isopropyl(F02879)
2D Structure
Description

Benthiavalicarb and benthiavalicarb-isopropyl, respectively, belong to the class of carbamate fungicides such as thiophanate and iprovalicarb. The mode of action of benthiavalicarb-isopropyl is to inhibit the incorporation of precursors required for phospholipid biosynthesis.

FRCD IDF02879
CAS Number177406-68-7
PubChem CID24848546
FormulaC18H24FN3O3S
IUPAC Name

propan-2-yl N-[(2R)-1-[[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]amino]-3-methyl-1-oxobutan-2-yl]carbamate

InChI Key

USRKFGIXLGKMKU-IAQYHMDHSA-N

InChI

InChI=1S/C18H24FN3O3S/c1-9(2)15(22-18(24)25-10(3)4)16(23)20-11(5)17-21-13-7-6-12(19)8-14(13)26-17/h6-11,15H,1-5H3,(H,20,23)(H,22,24)/t11-,15-/m1/s1

Canonical SMILES

CC(C)C(C(=O)NC(C)C1=NC2=C(S1)C=C(C=C2)F)NC(=O)OC(C)C

Isomeric SMILES

C[C@H](C1=NC2=C(S1)C=C(C=C2)F)NC(=O)[C@@H](C(C)C)NC(=O)OC(C)C

Synonyms
        
            USRKFGIXLGKMKU-IAQYHMDHSA-N
        
            ZINC43065291
        
            LS-191305
        
            J-011276
        
            isopropyl {(R)-1-[(R)-1-(6-fluorobenzothiazol-2-yl)ethylcarbamoyl]-2-methylpropyl}carbamate
        
            Benthiavalicarb isopropyl, PESTANAL(R), analytical standard
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentValine and derivatives
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsValine or derivatives - Alpha-amino acid amide - 1,3-benzothiazole - Aryl fluoride - Aryl halide - N-acyl-amine - Fatty acyl - Fatty amide - Benzenoid - Azole - Heteroaromatic compound - Carbamic acid ester - Thiazole - Carboxamide group - Secondary carboxylic acid amide - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Properties

Property NameProperty Value
Molecular Weight381.466
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Complexity506
Monoisotopic Mass381.152
Exact Mass381.152
XLogP3.9
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8460
Human Intestinal AbsorptionHIA+0.9898
Caco-2 PermeabilityCaco2-0.5987
P-glycoprotein SubstrateNon-substrate0.5694
P-glycoprotein InhibitorNon-inhibitor0.5077
Non-inhibitor0.9142
Renal Organic Cation TransporterNon-inhibitor0.9638
Distribution
Subcellular localizationMitochondria0.6766
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8717
CYP450 2D6 SubstrateNon-substrate0.8014
CYP450 3A4 SubstrateNon-substrate0.5367
CYP450 1A2 InhibitorInhibitor0.6306
CYP450 2C9 InhibitorInhibitor0.5180
CYP450 2D6 InhibitorNon-inhibitor0.9385
CYP450 2C19 InhibitorInhibitor0.5146
CYP450 3A4 InhibitorNon-inhibitor0.7682
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6463
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9968
Non-inhibitor0.7986
AMES ToxicityNon AMES toxic0.8007
CarcinogensNon-carcinogens0.8114
Fish ToxicityHigh FHMT0.9883
Tetrahymena Pyriformis ToxicityHigh TPT0.9112
Honey Bee ToxicityHigh HBT0.5232
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5459
Carcinogenicity (Three-class)Non-required0.6082
Model Value Unit
Absorption
Aqueous solubility-3.6076LogS
Caco-2 Permeability0.8974LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6788LD50, mol/kg
Fish Toxicity1.0612pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4518pIGC50, ug/L

Targets

Target Details

Cholinesterase

General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
Mechanism of Action:
Like the organophosphates, their mode of action is inhibition of cholinesterase enzymes, affecting nerve impulse transmission.
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088
Target Details

Acetylcholinesterase

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
References
  1. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension.: http://edis.ifas.ufl.edu/PI088