Protopine

Details

• Internal ID: 0e40230a-4a36-46cc-8300-2e236ad1a807
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 15-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
• SMILES (Canonical): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
• SMILES (Isomeric): CN1CCC2=CC3=C(C=C2C(=O)CC4=C(C1)C5=C(C=C4)OCO5)OCO3
• InChI: InChI=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
• InChI Key: GPTFURBXHJWNHR-UHFFFAOYSA-N
• Popularity: 260 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.40 g/mol
• Exact Mass: 353.12632271 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 130-86-9
• Corydinine
• Fumarine
• Biflorine
• Macleyine
• Protopin
• Hypercorine
• 7,13a-Secoberbin-13a-one, 7-methyl-2,3:9,10-bis(methylenedioxy)-
• CHEBI:16415
• HSDB 3527
• 7-Methyl-2,3:9,10-bis(methylenedioxy)-7,13a-secoberbin-13a-one
• EINECS 204-999-6
• UNII-UIW569HT35
• UIW569HT35
• AI3-62909
• 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c-5',6'-g)azecin-13(5H)-one
• 7-methyl-6,8,9,16-tetrahydrobis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-15(7H)-one
• Bis(1,3)benzodioxolo(4,5-C:5',6'-g)azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-
• CHEMBL453019
• 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[5',4':4,5]benzo[1,2-g]azecin-15(16H)-one
• DTXSID90156282
• Bis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one, 4,6,7,14-tetrahydro-5-methyl-
• Corydalis C
• 7-methyl-2,3:9,10-bis(methylenebis(oxy))-7,13a-secoberbin-13a-one
• 7-methyl-2,3:9,10-bis[methylenebis(oxy)]-7,13a-secoberbin-13a-one
• 7-methyl-6,8,9,16-tetrahydrobis(1,3)benzodioxolo(4,5-c:5',6'-g)azecin-15(7H)-one
• Alk-3
• Protopine (Corydinine)
• PROTOPINE [MI]
• Oprea1_718853
• Oprea1_722246
• Protopine, analytical standard
• SCHEMBL178013
• DTXCID7078773
• ACon1_001550
• GPTFURBXHJWNHR-UHFFFAOYSA-N
• HMS3428D22
• HMS3885M10
• HY-N0793
• TNP00339
• BDBM50286643
• CCG-36008
• HSCI1_000268
• MFCD00022322
• NSC781768
• s3883
• STL561430
• AKOS000278163
• CS-4249
• NSC-781768
• 4,6,7,14-Tetrahydro-5-methyl-bis[1,3]benzodioxolo[4,5-c-5,6-g]azecin-13(5H)-one
• NCGC00017389-01
• NCGC00017389-02
• NCGC00142402-01
• 7-methyl-4H,6H,8H,9H,12H,16H-1,3-dioxoleno[4''',5'''-3'',4'']benzo[1'',2''-8', 9']azecino[5',4'-2,1]benzo[4,5-d]1,3-dioxolan-15-one
• 7-Methyl-6,7,8,9-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[5',4':4,5]benzo[1,2-g]azecin-
• AC-34931
• BS-15163
• LS-144706
• FT-0674127
• P2611
• A14808
• C05189
• Q390706
• SR-05000002290
• SR-05000002290-2
• BRD-K83302049-001-01-6
• BRD-K83302049-003-01-2
• 2D13E16B-20F9-4670-AD3E-02EE26A53C9C
• 4,6,7,14-Tetrahydro-5-methyl-bis(1,3)benzodioxolo(4,5-c:5',6'-g)azecin-13(5h)-one
• 4,6,7,14-Tetrahydro-5-methylbis[1,3]benzodioxolo[4,5-c:5',6'-g]azecin-13(5H)-one
• 7-Methyl-6,8,9,16-tetrahydrodi[1,3]benzodioxolo[4,5-c:5,6-g]azecin-15(7H)-one #
• 15-methyl-7,9,19,21-tetraoxa-15-azapentacyclo[15.7.0.0^{4,12}.0^{6,10}.0^{18,22}]tetracosa-1(24),4(12),5,10,17,22-hexaen-3-one
• 15-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	+	0.8102	81.02%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5341	53.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9274	92.74%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8151	81.51%
P-glycoprotein inhibitior	-	0.4610	46.10%
P-glycoprotein substrate	-	0.7533	75.33%
CYP3A4 substrate	+	0.5208	52.08%
CYP2C9 substrate	-	0.8236	82.36%
CYP2D6 substrate	+	0.3945	39.45%
CYP3A4 inhibition	-	0.7379	73.79%
CYP2C9 inhibition	-	0.9081	90.81%
CYP2C19 inhibition	+	0.8993	89.93%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9490	94.90%
CYP inhibitory promiscuity	-	0.8129	81.29%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5416	54.16%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9223	92.23%
Skin irritation	-	0.7963	79.63%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7512	75.12%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8427	84.27%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.4614	46.14%
Acute Oral Toxicity (c)	III	0.7503	75.03%
Estrogen receptor binding	+	0.6468	64.68%
Androgen receptor binding	+	0.6076	60.76%
Thyroid receptor binding	-	0.7439	74.39%
Glucocorticoid receptor binding	+	0.5705	57.05%
Aromatase binding	+	0.5401	54.01%
PPAR gamma	+	0.6455	64.55%
Honey bee toxicity	-	0.8632	86.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9089	90.89%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3622	P33261	Cytochrome P450 2C19	10000 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	50.1 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	99.49%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	98.48%	93.40%
CHEMBL2581	P07339	Cathepsin D	97.93%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.49%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	92.06%	91.49%
CHEMBL4208	P20618	Proteasome component C5	91.58%	90.00%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	88.43%	90.95%
CHEMBL2056	P21728	Dopamine D1 receptor	87.93%	91.00%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	87.47%	81.29%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.97%	94.80%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.56%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.88%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.44%	91.11%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	82.89%	82.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.52%	90.71%
CHEMBL5805	Q9NR97	Toll-like receptor 8	82.36%	96.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.10%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.71%	89.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.64%	93.65%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.92%	82.67%
CHEMBL2535	P11166	Glucose transporter	80.10%	98.75%

Plants that contains it

• Allium sativum
• Aloe microstigma
• Angelica dahurica
• Arctomecon merriamii
• Argemone grandiflora
• Argemone mexicana
• Argemone munita
• Argemone ochroleuca
• Argemone polyanthemos
• Argemone subfusiformis
• Artabotrys maingayi
• Berberis darwinii
• Berberis empetrifolia
• Berberis laurina
• Bocconia frutescens
• Caltha palustris
• Capnoides sempervirens
• Ceratocapnos claviculata
• Chelidonium majus
• Chrozophora plicata
• Corydalis ambigua
• Corydalis balansae
• Corydalis bulleyana
• Corydalis bungeana
• Corydalis calliantha
• Corydalis campulicarpa
• Corydalis caucasica
• Corydalis cava
• Corydalis cheilanthifolia
• Corydalis decumbens
• Corydalis gortschakovii
• Corydalis govaniana
• Corydalis heterocarpa
• Corydalis incisa
• Corydalis ledebouriana
• Corydalis meifolia
• Corydalis nobilis
• Corydalis ophiocarpa
• Corydalis orthopoda
• Corydalis pallida
• Corydalis paniculigera
• Corydalis pseudoadunca
• Corydalis racemosa
• Corydalis rutifolia
• Corydalis saxicola
• Corydalis sewerzowi
• Corydalis solida
• Corydalis speciosa
• Corydalis stricta
• Corydalis ternata
• Corydalis thyrsiflora
• Corydalis turtschaninovii
• Corydalis vaginans
• Corydalis yanhusuo
• Cyclea atjehensis
• Cyperus nipponicus
• Dactylicapnos torulosa
• Dalbergia spruceana
• Dendrobium amplum
• Dicentra formosa
• Diospyros ebenum
• Erythrophleum suaveolens
• Eschscholzia californica
• Fumaria agraria
• Fumaria bracteosa
• Fumaria capreolata
• Fumaria densiflora
• Fumaria gaillardotii
• Fumaria indica
• Fumaria officinalis
• Fumaria parviflora
• Fumaria rostellata
• Fumaria vaillantii
• Galanthus trojanus
• Glaucium elegans
• Glaucium fimbrilligerum
• Glaucium flavum
• Glaucium grandiflorum
• Glaucium leiocarpum
• Glaucium squamigerum
• Horsfieldia glabra
• Hunnemannia fumariifolia
• Hylomecon japonica
• Hypecoum erectum
• Hypecoum imberbe
• Hypecoum leptocarpum
• Hypecoum pendulum
• Hypecoum procumbens
• Ichtyoselmis macrantha
• Lappula squarrosa
• Larix decidua
• Ligularia sagitta
• Macleaya cordata
• Meconopsis napaulensis
• Meconopsis robusta
• Mezzettia parviflora
• Nuxia sphaerocephala
• Panax ginseng
• Papaver albiflorum
• Papaver atlanticum
• Papaver bracteatum
• Papaver canescens
• Papaver curviscapum
• Papaver dubium
• Papaver heterophyllum
• Papaver lapponicum
• Papaver lateritium
• Papaver oreophilum
• Papaver orientale
• Papaver pavoninum
• Papaver pinnatifidum
• Papaver pygmaeum
• Papaver rhoeas
• Papaver somniferum
• Papaver somniferum subsp. setigerum
• Phellodendron amurense
• Phellodendron chinense
• Piper methysticum
• Platycapnos saxicola
• Platystemon californicus
• Prunus humilis
• Psacalium peltatum
• Roemeria refracta
• Sanguinaria canadensis
• Sarcocapnos baetica
• Sarcocapnos crassifolia
• Sarcocapnos enneaphylla
• Senna spectabilis
• Stachys plumosa
• Stylophorum diphyllum
• Stylophorum lasiocarpum
• Swertia mussotii
• Symphytum officinale
• Thalictrum delavayi
• Thalictrum foetidum
• Thalictrum minus
• Thalictrum revolutum
• Thalictrum simplex
• Thuja plicata
• Ulex parviflorus subsp. airensis
• Vepris heterophylla
• Zanthoxylum vitiense

Cross-Links

• PubChem: 4970
• NPASS: NPC308267
• ChEMBL: CHEMBL453019
• LOTUS: LTS0080245
• wikiData: Q390706