Basic Info

Common NameNaptalam(F05736)
2D Structure
FRCD IDF05736
CAS Number132-66-1
PubChem CID8594
FormulaC18H13NO3
IUPAC Name

2-(naphthalen-1-ylcarbamoyl)benzoic acid

InChI Key

JXTHEWSKYLZVJC-UHFFFAOYSA-N

InChI

InChI=1S/C18H13NO3/c20-17(14-9-3-4-10-15(14)18(21)22)19-16-11-5-7-12-6-1-2-8-13(12)16/h1-11H,(H,19,20)(H,21,22)

Canonical SMILES

C1=CC=C2C(=C1)C=CC=C2NC(=O)C3=CC=CC=C3C(=O)O

Isomeric SMILES

C1=CC=C2C(=C1)C=CC=C2NC(=O)C3=CC=CC=C3C(=O)O

Synonyms
        
            Grelutin
        
            Peach-Thin
        
            NAPTALAM
        
            132-66-1
        
            Alanap
        
            Alanape
        
            Analape
        
            Dyanap
        
            N-1-Naphthylphthalamic acid
        
            Mor-Cran
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassNaphthalenes
SubclassNot available
Intermediate Tree NodesNot available
Direct ParentNaphthalenes
Alternative Parents
Molecular FrameworkAromatic homopolycyclic compounds
SubstituentsNaphthalene - Benzamide - Benzoic acid or derivatives - Benzoic acid - Benzoyl - Monocyclic benzene moiety - Carboxamide group - Secondary carboxylic acid amide - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic homopolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Properties

Property NameProperty Value
Molecular Weight291.306
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity423
Monoisotopic Mass291.09
Exact Mass291.09
XLogP3.5
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
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+0.9657
Human Intestinal AbsorptionHIA+0.9571
Caco-2 PermeabilityCaco2+0.6303
P-glycoprotein SubstrateNon-substrate0.7991
P-glycoprotein InhibitorNon-inhibitor0.9237
Non-inhibitor0.9074
Renal Organic Cation TransporterNon-inhibitor0.9477
Distribution
Subcellular localizationMitochondria0.6605
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7691
CYP450 2D6 SubstrateNon-substrate0.8640
CYP450 3A4 SubstrateNon-substrate0.6667
CYP450 1A2 InhibitorInhibitor0.6886
CYP450 2C9 InhibitorNon-inhibitor0.9053
CYP450 2D6 InhibitorNon-inhibitor0.9146
CYP450 2C19 InhibitorNon-inhibitor0.9179
CYP450 3A4 InhibitorNon-inhibitor0.9774
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9279
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9938
Non-inhibitor0.9212
AMES ToxicityNon AMES toxic0.7465
CarcinogensNon-carcinogens0.7292
Fish ToxicityHigh FHMT0.8956
Tetrahymena Pyriformis ToxicityLow TPT0.7748
Honey Bee ToxicityLow HBT0.8511
BiodegradationNot ready biodegradable0.7392
Acute Oral ToxicityIV0.7207
Carcinogenicity (Three-class)Non-required0.6652

Model Value Unit
Absorption
Aqueous solubility-3.8825LogS
Caco-2 Permeability1.2336LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5827LD50, mol/kg
Fish Toxicity1.4384pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.0373pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Muskmelons (Other Than Those Listed In This Item)Canada0.1mg/kg
Other Cucurbitaceous VegetablesJapan0.1ppm
Makuwauri MelonJapan0.1ppm
MelonsJapan0.1ppm
Water MelonJapan0.1ppm
Oriental Pickling Melon(Vegetable)Japan0.1ppm
Pumpkin(Including Squash)Japan0.1ppm
Cucumber(Including Gherkin)Japan0.1ppm
CantaloupesCanada0.1mg/kg
Citron MelonsCanada0.1mg/kg
CucumbersCanada0.1mg/kg
WatermelonsCanada0.1mg/kg

References

TitleJournalDatePubmed ID
Auxin Biosynthesis, Accumulation, Action and Transport are Involved inStress-Induced Microspore Embryogenesis Initiation and Progression in Brassicanapus.Plant Cell Physiol2015 Jul25907568
Antiadhesion as a functional concept for prevention of pathogens: N-Phenylpropenoyl-L-amino acid amides as inhibitors of the Helicobacter pylori BabA outer membrane protein.Mol Nutr Food Res2011 Jul21520488
Inhibition of auxin transport from the ovary or from the apical shoot inducesparthenocarpic fruit-set in tomato mediated by gibberellins.Plant Physiol2010 Jun20388661
Inhibited polar auxin transport results in aberrant embryo development in Norway spruce.New Phytol200818042199
Interactions between auxin transport and the actin cytoskeleton in developmental polarity of Fucus distichus embryos in response to light and gravity.Plant Physiol2004 May15122028