Basic Info

Common NameProhexadione(F06324)
2D Structure
FRCD IDF06324
CAS Number88805-35-0
PubChem CID184900
FormulaC10H12O5
IUPAC Name

3,5-dioxo-4-propanoylcyclohexane-1-carboxylic acid

InChI Key

BUCOQPHDYUOJSI-UHFFFAOYSA-N

InChI

InChI=1S/C10H12O5/c1-2-6(11)9-7(12)3-5(10(14)15)4-8(9)13/h5,9H,2-4H2,1H3,(H,14,15)

Canonical SMILES

CCC(=O)C1C(=O)CC(CC1=O)C(=O)O

Isomeric SMILES

CCC(=O)C1C(=O)CC(CC1=O)C(=O)O

Synonyms
        
            Prohexadione
        
            DOCHC
        
            88805-35-0
        
            UNII-4PC163MD7L
        
            4PC163MD7L
        
            3,5-Dioxo-4-propionylcyclohexanecarboxylic acid
        
            3,5-dioxo-4-propanoylcyclohexanecarboxylic acid
        
            3,5-dioxo-4-propanoylcyclohexane-1-carboxylic acid
        
            Cyclohexanecarboxylicacid, 3,5-dioxo-4-(1-oxopropyl)-
        
            Prohexadione [ISO]
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree Nodes1,3-dicarbonyl compounds
Direct ParentBeta-diketones
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
Substituents1,3-diketone - Cyclic ketone - Ketone - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.

Properties

Property NameProperty Value
Molecular Weight212.201
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Complexity313
Monoisotopic Mass212.068
Exact Mass212.068
XLogP-0.4
Formal Charge0
Heavy Atom Count15
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+0.8711
Human Intestinal AbsorptionHIA+0.9860
Caco-2 PermeabilityCaco2-0.5240
P-glycoprotein SubstrateNon-substrate0.7584
P-glycoprotein InhibitorNon-inhibitor0.8851
Non-inhibitor0.9821
Renal Organic Cation TransporterNon-inhibitor0.9124
Distribution
Subcellular localizationMitochondria0.9046
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8354
CYP450 2D6 SubstrateNon-substrate0.9104
CYP450 3A4 SubstrateNon-substrate0.7168
CYP450 1A2 InhibitorNon-inhibitor0.9882
CYP450 2C9 InhibitorNon-inhibitor0.9539
CYP450 2D6 InhibitorNon-inhibitor0.9358
CYP450 2C19 InhibitorNon-inhibitor0.9439
CYP450 3A4 InhibitorNon-inhibitor0.9528
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9914
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9176
Non-inhibitor0.9871
AMES ToxicityNon AMES toxic0.8853
CarcinogensNon-carcinogens0.8464
Fish ToxicityHigh FHMT0.8280
Tetrahymena Pyriformis ToxicityHigh TPT0.7486
Honey Bee ToxicityHigh HBT0.7611
BiodegradationReady biodegradable0.7667
Acute Oral ToxicityIII0.7085
Carcinogenicity (Three-class)Non-required0.7417

Model Value Unit
Absorption
Aqueous solubility-1.2501LogS
Caco-2 Permeability0.5679LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1413LD50, mol/kg
Fish Toxicity1.6298pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.6107pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Cherries (sweet) (Black cherries, Capulins, Chokecherries, Cornelian cherries/European corniols, Nanking cherries, Sour cherries/morello cherries,)0140020European Union0.406/02/2018
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*06/02/2018
Aubergines/eggplants (Antroewas/African eggplants/gboma, Ethiopian eggplants/gilo', Pepinos, Thorn apples, Turkey berries/devil's figs/pea eggplants/pea aubergines, Kangaroo apples/poroporo,)0231030European Union0.01*06/02/2018
Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou...0251040European Union0.01*06/02/2018
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.05*06/02/2018
(g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh...1017000European Union0.01*06/02/2018
Citrus fruits0110000European Union0.01*06/02/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*06/02/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*06/02/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*06/02/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*06/02/2018
Figs0161020European Union0.01*06/02/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.01*06/02/2018
Brazil nuts0120020European Union0.01*06/02/2018
Cashew nuts0120030European Union0.01*06/02/2018
Chestnuts0120040European Union0.01*06/02/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.01*06/02/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.01*06/02/2018
Macadamias0120070European Union0.01*06/02/2018
Pecans (Hickory nuts,)0120080European Union0.01*06/02/2018