Fenprostalene

Basic Info

Common NameFenprostalene(F05685)
2D Structure
FRCD IDF05685
CAS Number
PubChem CID6435068
FormulaC23H30O6
IUPAC Name

methyl 7-[(1R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]cyclopentyl]hepta-4,5-dienoate

InChI Key

BYNHBQROLKAEDQ-PASQQFGNSA-N

InChI

InChI=1S/C23H30O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-22,24-26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17-,19-,20?,21+,22-/m1/s1

Canonical SMILES

COC(=O)CCC=C=CCC1C(CC(C1C=CC(COC2=CC=CC=C2)O)O)O

Isomeric SMILES

COC(=O)CCC=C=CC[C@H]1[C@H](C[C@H](C1/C=C/[C@H](COC2=CC=CC=C2)O)O)O

Synonyms
        
            Fenprostalene [USAN:BAN:INN]
        
            Methyl (+-)-7-((1R*,2R*,3R*,5S*)-3,5-dihydroxy-2-((E)-(3R*)-3-hydroxy-4-phenoxy-1-butenyl)cyclopentyl)-4,5-heptadienoate
        
            FENPROSTALENE
        
            Synchrocept B
        
            Synchrocept B (Veterinary)
        
            Fenprostalenum [INN-Latin]
        
            Fenprostaleno [INN-Spanish]
        
            EINECS 273-982-3
        
            AC1O5J1Y
        
            4,5-Heptadienoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)cyclopentyl)-, methyl ester
Classifies
                

                  
                    Predicted: Animal Toxin
Update DateNov 13, 2018 17:07

Properties

Property NameProperty Value
Molecular Weight402.487
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count11
Complexity574
Monoisotopic Mass402.204
Exact Mass402.204
XLogP1.6
Formal Charge0
Heavy Atom Count29
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5234
Human Intestinal AbsorptionHIA+0.9147
Caco-2 PermeabilityCaco2-0.5108
P-glycoprotein SubstrateSubstrate0.6361
P-glycoprotein InhibitorNon-inhibitor0.8624
Non-inhibitor0.6520
Renal Organic Cation TransporterNon-inhibitor0.7853
Distribution
Subcellular localizationMitochondria0.8852
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7740
CYP450 2D6 SubstrateNon-substrate0.8500
CYP450 3A4 SubstrateSubstrate0.5752
CYP450 1A2 InhibitorNon-inhibitor0.6624
CYP450 2C9 InhibitorNon-inhibitor0.8626
CYP450 2D6 InhibitorNon-inhibitor0.9086
CYP450 2C19 InhibitorNon-inhibitor0.7885
CYP450 3A4 InhibitorNon-inhibitor0.8255
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8343
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9183
Non-inhibitor0.7206
AMES ToxicityNon AMES toxic0.7513
CarcinogensNon-carcinogens0.9613
Fish ToxicityHigh FHMT0.9862
Tetrahymena Pyriformis ToxicityHigh TPT0.9998
Honey Bee ToxicityHigh HBT0.7218
BiodegradationReady biodegradable0.6927
Acute Oral ToxicityI0.5849
Carcinogenicity (Three-class)Non-required0.7600
Model Value Unit
Absorption
Aqueous solubility-2.5519LogS
Caco-2 Permeability0.3861LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity3.2470LD50, mol/kg
Fish Toxicity1.3210pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.5008pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Fat Of CattleUnited States0.ppb(safe concentrations)
Kidney Of CattleUnited States30ppb(safe concentrations)
Muscle Of CattleUnited States10ppb(safe concentrations)
CattleUnited States0.t needed
Cattle,Edible OffalJapan0.02ppm
Cattle,KidneyJapan0.03ppm
Cattle,LiverJapan0.02ppm
Cattle,FatJapan0.04ppm
Cattle,MuscleJapan0.01ppm
Liver Of CattleUnited States20ppb(safe concentrations)