Aurantiol

Basic Info

Common NameAurantiol(F02386)
2D Structure
FRCD IDF02386
CAS Number89-43-0
PubChem CID98118
FormulaC18H27NO3
IUPAC Name

methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate

InChI Key

BFBPISPWJZMWJN-UHFFFAOYSA-N

InChI

InChI=1S/C18H27NO3/c1-14(8-7-12-18(2,3)21)11-13-19-16-10-6-5-9-15(16)17(20)22-4/h5-6,9-10,13-14,21H,7-8,11-12H2,1-4H3

Canonical SMILES

CC(CCCC(C)(C)O)CC=NC1=CC=CC=C1C(=O)OC

Isomeric SMILES

CC(CCCC(C)(C)O)CC=NC1=CC=CC=C1C(=O)OC

Synonyms
        
            Aurantiol
        
            Aurantium
        
            Hydroxycitronellylidene methyl anthranilate
        
            NSC-78483
        
            EINECS 201-908-1
        
            Methyl N-3,7-dimethyl-7-hydroxyoctylideneanthranilate
        
            Methyl 2-((7-hydroxy-3,7-dimethyloctylidene)amino)benzoate
        
            Aurantion
        
            89-43-0
        
            methyl 2-[(7-hydroxy-3,7-dimethyloctylidene)amino]benzoate
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 16:49

Properties

Property NameProperty Value
Molecular Weight305.418
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count9
Complexity365
Monoisotopic Mass305.199
Exact Mass305.199
XLogP3.3
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8403
Human Intestinal AbsorptionHIA+0.7945
Caco-2 PermeabilityCaco2+0.5589
P-glycoprotein SubstrateSubstrate0.5443
P-glycoprotein InhibitorNon-inhibitor0.5455
Inhibitor0.5633
Renal Organic Cation TransporterNon-inhibitor0.7250
Distribution
Subcellular localizationMitochondria0.8713
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6997
CYP450 2D6 SubstrateNon-substrate0.7821
CYP450 3A4 SubstrateSubstrate0.6479
CYP450 1A2 InhibitorNon-inhibitor0.6977
CYP450 2C9 InhibitorNon-inhibitor0.7307
CYP450 2D6 InhibitorNon-inhibitor0.8385
CYP450 2C19 InhibitorNon-inhibitor0.7589
CYP450 3A4 InhibitorNon-inhibitor0.7935
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7781
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9689
Non-inhibitor0.7659
AMES ToxicityNon AMES toxic0.7378
CarcinogensNon-carcinogens0.7825
Fish ToxicityHigh FHMT0.9710
Tetrahymena Pyriformis ToxicityHigh TPT0.9989
Honey Bee ToxicityLow HBT0.6251
BiodegradationNot ready biodegradable0.9793
Acute Oral ToxicityIII0.6569
Carcinogenicity (Three-class)Non-required0.6351
Model Value Unit
Absorption
Aqueous solubility-3.9806LogS
Caco-2 Permeability1.1608LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3336LD50, mol/kg
Fish Toxicity0.8404pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.1633pIGC50, ug/L

References

TitleJournalDatePubmed ID
Comparative analysis of juice volatiles in selected mandarins, mandarin relativesand other citrus genotypes.J Sci Food Agric2018 Feb28731231
Effects of acute ingestion of a pre-workout dietary supplement with and withoutp-synephrine on resting energy expenditure, cognitive function and exerciseperformance.J Int Soc Sports Nutr2017 Jan 1228096758
Hepatoprotective effects of polymethoxyflavones against acute and chronic carbon tetrachloride intoxication.Food Chem Toxicol2016 May26980244
Anti-HIV-1 activity of eight monofloral Iranian honey types.PLoS One2014 Oct 2125333699
Biotransformations of terpenes by fungi from Amazonian citrus plants.Chem Biodivers2013 Oct24130034
Characterization of essential oil from Citrus aurantium L. flowers: antimicrobialand antioxidant activities.J Oleo Sci201324088513
Season's variation impact on Citrus aurantium leaves essential oil: chemicalcomposition and biological activities.J Food Sci2012 Sep22897411
Nutrients and nonessential elements in soil after 11 years of wastewaterirrigation.J Environ Qual2012 May-Jun22565273
Induction of the cell cycle arrest and apoptosis by flavonoids isolated fromKorean Citrus aurantium L. in non-small-cell lung cancer cells.Food Chem2012 Dec 1522980865
Bioactivity evaluations of ingredients extracted from the flowers of Citrusaurantium L. var. amara Engl.Food Chem2012 Dec 1522980787
Insecticidal activity against Bemisia tabaci biotype B of peel essential oil ofCitrus sinensis var. pear and Citrus aurantium cultivated in northeast Brazil.Nat Prod Commun2010 Nov21213990
Acaricidal activity against Tetranychus urticae and chemical composition of peel essential oils of three Citrus species cultivated in NE Brazil.Nat Prod Commun2010 Mar20420330
Isolation and identification of insecticidal components from Citrus aurantium fruit peel extract.J Agric Food Chem2008 Jul 2318578532
Radical scavenging activities of Rio Red grapefruits and Sour orange fruitextracts in different in vitro model systems.Bioresour Technol2008 Jul17935981
Evaluation of some pollutant levels in bitter orange trees: implications forhuman health.Food Chem Toxicol2008 Jan17681412
Insecticidal activity of Citrus aurantium fruit, leaf, and shoot extracts againstadult olive fruit flies (Diptera: Tephritidae).J Econ Entomol2007 Aug17849873
Antibacterial properties of tropical plants from Puerto Rico.Phytomedicine2006 Mar16492531