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Corydine

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

Canonical Smiles	COc1cc2CCN([C@@H]3c2c(c1O)c1c(C3)ccc(c1OC)OC)C
InChI	InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)19(22)18-16(12)13(21)9-11-5-6-14(23-2)20(25-4)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1
InChIKey	IDQUPXZJURZAGF-ZDUSSCGKSA-N
Formula	C₂₀H₂₃NO₄
HBA	5
HBD	1
MW	341.41
Rotatable Bonds	3
TPSA	51.16
LogP	3.17
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	341.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Glaucium corniculatum	Papaveraceae	Plantae	1533087

Showing of synonyms

Al-Wakeel SAM, Moubasher MH, et al. (1995). Alkaloids from Glaucium corniculatum (L.) of Egyptian origin. Biochemical Systematics and Ecology,1995,23(3),337-338. [View]

Pubchem: 10153

Cas: 476-69-7

Gnps: CCMSLIB00006525128

Zinc: ZINC000001651264

Nmrshiftdb2: 60026211

Chembl: CHEMBL489524

Bindingdb: 50250271

CPRiL: 249117

SMILES: c1cccc(c1c23)CC4c2c(ccc3)CCN4

Level: 0

Mol. Weight: 341.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.790
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.920
Plasma Protein Binding: 54.14
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.010
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.920
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.600
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.770
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: Safe
T. Pyriformis: -4.550
Rat (Acute): 2.600
Rat (Chronic Oral): 1.900
Fathead Minnow: 4.690
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 403.330
Hydration Free Energy: -9.160
Log(D) at pH=7.4: 2.620
Log(P): 1.87
Log S: -2.66
Log(Vapor Pressure): -7.45
Melting Point: 169.39
pKa Acid: 9.46
pKa Basic: 8.28

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9256
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9256
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8995
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8995
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8782
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.8782
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8576
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8576
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8552
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8552
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8518
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8518
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8463
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8463
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8394
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8394
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8365
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8365
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8269
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8269
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8234
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8234
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8224
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8224
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8089
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8089
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8058
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8058
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8030
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8030
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.8008
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.8008
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7986
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7986
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7954
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7954
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7829
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	3	0.7829
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7640
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7640
Putative snRNP Sm-like protein	Q8ZYG5	Q8ZYG5_PYRAE	Pyrobaculum aerophilum	3	0.7633
Putative snRNP Sm-like protein	Q8ZYG5	Q8ZYG5_PYRAE	Pyrobaculum aerophilum	3	0.7633
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7614
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7614
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7568
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.7568
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7493
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7493
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7489
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7489
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7469
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7469
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7468
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7468
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7451
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7451
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7443
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7443
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7384
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7384
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7365
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7362
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7362
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7330
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7330
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7295
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7295
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7285
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7285
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7273
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7273
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7272
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7272
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7239
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7239
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7222
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7222
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7220
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7220
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7147
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7147
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7145
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7145
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7126
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7126
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7122
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7122
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7091
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7091
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7081
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7081
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase	P23970	MEND_BACSU	Bacillus subtilis	3	0.7063
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase	P23970	MEND_BACSU	Bacillus subtilis	3	0.7063
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7046
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7046
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7043
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7043
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7041
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7041
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7013
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7013
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7003
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7003

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