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Bocconoline

Family: Plantae - Papaveraceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid

Canonical Smiles	OCC1c2c(ccc(c2OC)OC)c2c(N1C)c1cc3OCOc3cc1cc2
InChI	InChI=1S/C22H21NO5/c1-23-16(10-24)20-13(6-7-17(25-2)22(20)26-3)14-5-4-12-8-18-19(28-11-27-18)9-15(12)21(14)23/h4-9,16,24H,10-11H2,1-3H3
InChIKey	GKBDCSXIKLSKMH-UHFFFAOYSA-N
Formula	C₂₂H₂₁NO₅
HBA	6
HBD	1
MW	379.41
Rotatable Bonds	3
TPSA	60.39
LogP	3.74
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	379.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Glaucium flavum	Papaveraceae	Plantae	56853

Showing of synonyms

Bournine L, Bensalem S, et al. (2013). Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum. International Journal of Molecular Sciences,2013,14(12),23533-23544. [View] [PubMed]

Pubchem: 181121

Cas: 32906-88-0

Nmrshiftdb2: 60022939

Chembl: CHEMBL4754766

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c(c2)c4c(cc3)c5c(CN4)cccc5

Level: 0

Mol. Weight: 379.41 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -5.08
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.57
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.31
Plasma Protein Binding: 71.77
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 14.38
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.44
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.98
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.47
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -23.26
Rat (Acute): 2.8
Rat (Chronic Oral): 1.85
Fathead Minnow: 5.35
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 497.97
Hydration Free Energy: -5.41
Log(D) at pH=7.4: 2.85
Log(P): 3.48
Log S: -4.11
Log(Vapor Pressure): -9.94
Melting Point: 155.93
pKa Acid: 10.82
pKa Basic: 5.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9686
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9686
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9664
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9664
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9556
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9556
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9358
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9358
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9133
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9133
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8982
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8982
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8971
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8971
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8889
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8889
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8855
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8855
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8787
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8787
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8602
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8602
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8567
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8567
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8566
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8566
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8526
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8526
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8524
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8524
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8327
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8327
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8307
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8307
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8289
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8289
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8284
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8284
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8149
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8149
Cytochrome P450 2B4	P00178	CP2B4_RABIT	Oryctolagus cuniculus	3	0.8140
Cytochrome P450 2B4	P00178	CP2B4_RABIT	Oryctolagus cuniculus	3	0.8140
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8093
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8093
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8059
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8059
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8015
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8015
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8006
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.8006
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.8000
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.8000
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7883
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7883
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7883
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7883
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7807
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7807
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7751
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7751
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7750
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7750
Cytochrome P450 2D6	P10635	CP2D6_HUMAN	Homo sapiens	3	0.7662
Cytochrome P450 2D6	P10635	CP2D6_HUMAN	Homo sapiens	3	0.7662
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7553
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7553
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7536
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7536
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7513
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7513
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7508
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7508
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7455
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7455
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7440
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7440
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7410
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7410
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7409
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7409
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7407
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7407
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7390
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7390
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7354
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7354
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7348
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7348
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7346
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7346
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	3	0.7337
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	3	0.7337
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7292
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7292
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7283
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7283
Bromodomain protein, putative	Q8I240	Q8I240_PLAF7	Plasmodium falciparum	4	0.7268
Bromodomain protein, putative	Q8I240	Q8I240_PLAF7	Plasmodium falciparum	4	0.7268
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7263
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7263
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7257
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7257
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	4	0.7243
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	4	0.7243
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7204
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7204
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7195
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7195
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7162
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7162
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7159
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7159
(RS)-norcoclaurine 6-O-methyltransferase	Q5C9L7	6OMT_THLFG	Thalictrum flavum subsp. glaucum	3	0.7154
(RS)-norcoclaurine 6-O-methyltransferase	Q5C9L7	6OMT_THLFG	Thalictrum flavum subsp. glaucum	3	0.7154
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	4	0.7130
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	4	0.7130
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7120
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7120
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7119
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7119
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7102
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7102
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7096
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7096
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7090
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7090
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7088
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7088
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7076
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7076
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7053
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7053
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	3	0.7012
L-methionine gamma-lyase	Q84AR1	Q84AR1_CITFR	Citrobacter freundii	3	0.7012
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7007
Enterochelin uptake periplasmic binding protein	Q0P8Q4	Q0P8Q4_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7007
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7006
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7006
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7005
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.7005
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7004
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7004
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7001
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7001

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