ANPDB

Select a section from the left sidebar

(±)-hypecorinine

Family: Plantae - Hypecoaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Aporphine Alkaloid

Canonical Smiles	CN1CCc2c(C31OCc1c(C3=O)ccc3c1OCO3)cc1c(c2)OCO1
InChI	InChI=1S/C20H17NO6/c1-21-5-4-11-6-16-17(25-9-24-16)7-14(11)20(21)19(22)12-2-3-15-18(26-10-23-15)13(12)8-27-20/h2-3,6-7H,4-5,8-10H2,1H3
InChIKey	DFLLMUXSZJESOF-UHFFFAOYSA-N
Formula	C₂₀H₁₇NO₆
HBA	7
HBD	0
MW	367.36
Rotatable Bonds	0
TPSA	66.46
LogP	2.2
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	367.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypecoum procumbens	Hypecoaceae	Plantae	391933

Showing of synonyms

Saad HEA (1995). (±)-8-oxohypecorinine from Hypecoum procumbens Var. Glaucescens. Phytochemistry,1995,38(4),1049-1051. [View]

Pubchem: 13997263

Cas: 41787-57-9

Nmrshiftdb2: 70081732

Chembl: CHEMBL4173190

Bindingdb: 50286644

No compound-protein relationship available.

SMILES: O1COc(cc2)c1c(CO3)c2C(=O)C34c5c(CCN4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 367.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.97
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.6
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 50.36
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 17.43
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.4
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.4
Micronucleos: Toxic
NR-AhR: Safe
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: -19.36
Rat (Acute): 2.29
Rat (Chronic Oral): 0.79
Fathead Minnow: 4.66
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 441.27
Hydration Free Energy: -5.4
Log(D) at pH=7.4: 2.56
Log(P): 2.9
Log S: -4.15
Log(Vapor Pressure): -10.4
Melting Point: 178.32
pKa Acid: 7.92
pKa Basic: 4.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8930
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8930
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8610
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8610
Beta-adrenergic receptor kinase 1	P25098	ARBK1_HUMAN	Homo sapiens	3	0.8451
Beta-adrenergic receptor kinase 1	P25098	ARBK1_HUMAN	Homo sapiens	3	0.8451
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8257
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8257
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8223
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8223
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8204
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8204
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.8159
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.8159
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8146
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8146
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8127
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8127
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8084
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8084
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8063
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8063
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8048
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8048
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7982
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7982
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7891
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7891
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7823
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7823
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7766
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7766
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7718
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7718
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7697
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7697
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7682
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7682
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7681
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7681
Lanosterol 14-alpha demethylase	A6ZSR0	A6ZSR0_YEAS7	Saccharomyces cerevisiae	3	0.7642
Lanosterol 14-alpha demethylase	A6ZSR0	A6ZSR0_YEAS7	Saccharomyces cerevisiae	3	0.7642
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7613
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7613
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7548
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7548
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7520
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7520
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7480
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7480
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7464
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7464
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7432
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7432
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7431
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7431
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7398
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7398
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7364
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7364
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7339
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7339
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7329
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7329
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7329
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7329
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7327
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7327
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7327
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.7327
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7312
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7312
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7296
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7296
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7292
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7292
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7263
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7263
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7261
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7261
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7217
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7217
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7187
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7187
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7169
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7169
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7125
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7125
Cytochrome P450 2C19	P33261	CP2CJ_HUMAN	Homo sapiens	3	0.7116
Cytochrome P450 2C19	P33261	CP2CJ_HUMAN	Homo sapiens	3	0.7116
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7114
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7114
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.7071
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.7071
Heat shock protein 75 kDa, mitochondrial	Q12931	TRAP1_HUMAN	Homo sapiens	3	0.7050
Heat shock protein 75 kDa, mitochondrial	Q12931	TRAP1_HUMAN	Homo sapiens	3	0.7050
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7043
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7043
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7039
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7039
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7035
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7035
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7004
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7004
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7001
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7001

Download SDF