Protopine

Basic Info

FADB-China IDC0443
Substance NameHoney
Substance Chinese Name蜂蜜
Molecular NameProtopine
Molecular Chinese Name原嘌呤
2D StructureNo image
CAS Number130-86-9
PubChem CID4970
FormulaC20H19NO5
IUPAC Name15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.04,12.06,10.018,22]tetracosa-1(17),4,6(10),11,18(22),23-hexaen-3-one
InChI KeyGPTFURBXHJWNHR-UHFFFAOYSA-N
InChIInChI=1S/C20H19NO5/c1-21-5-4-13-7-18-19(25-10-24-18)8-14(13)16(22)6-12-2-3-17-20(15(12)9-21)26-11-23-17/h2-3,7-8H,4-6,9-11H2,1H3
Canonical SMILES

CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3

Isomeric SMILES

CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3

CFM-ID 3.0URL Link
Related linksProcessing
Addition PurposesNone
Molecular Synonyms
        
            Protopine
        
            130-86-9
        
            Corydinine
        
            Biflorine
        
            Macleyine
        
            Hypercorine
        
            Protopin
        
            UNII-UIW569HT35
        
            HSDB 3527
        
            Fumarine
Data UploaderShuyu Ouyang
Update DateJul 25, 2019 20:46

Properties

Property NameProperty Value
Molecular Weight353.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Complexity542
Monoisotopic Mass353.12632272
Exact Mass353.12632272
XLogP2.8
Formal Charge0
Heavy Atom Count26
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+0.9810
Human Intestinal AbsorptionHIA+0.9937
Caco-2 PermeabilityCaco2+0.7897
P-glycoprotein SubstrateSubstrate0.7069
P-glycoprotein InhibitorNon-inhibitor0.6999
Non-inhibitor0.9594
Renal Organic Cation TransporterInhibitor0.6428
Distribution
Subcellular localizationLysosome0.5341
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8378
CYP450 2D6 SubstrateSubstrate0.5212
CYP450 3A4 SubstrateSubstrate0.6502
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9081
CYP450 2D6 InhibitorInhibitor0.8931
CYP450 2C19 InhibitorInhibitor0.8993
CYP450 3A4 InhibitorNon-inhibitor0.7379
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8129
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.6267
Non-inhibitor0.8853
AMES ToxicityAMES toxic0.7050
CarcinogensNon-carcinogens0.9428
Fish ToxicityHigh FHMT0.9735
Tetrahymena Pyriformis ToxicityHigh TPT0.9329
Honey Bee ToxicityLow HBT0.6332
BiodegradationReady biodegradable0.5468
Acute Oral ToxicityIII0.7503
Carcinogenicity (Three-class)Non-required0.5416

ADMET -- Regression

Model Value Unit
Aqueous solubility-2.8880LogS
Caco-2 Permeability1.4339LogPapp, cm/s
Rat Acute Toxicity2.3873LD50, mol/kg
Fish Toxicity1.0291pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4287pIGC50, ug/L

Related Foods

FADB-China ID F0090
Food Image No Pictures
Food Name Honey
Food Chinese Name 蜂蜜
Food Type Processed food
References Use of isoquinoline alkaloids as markers for identification of honey and pollen from Macleaya cordata (Willd.) R. Br

References

TitleDOI/PubMed/ISSN
Use of isoquinoline alkaloids as markers for identification of honey and pollen from Macleaya cordata (Willd.) R. Br