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(7R,14S)-trans-N-methylstylopine

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

Canonical Smiles	C[N@+]12CCc3c([C@@H]2Cc2c(C1)c1OCOc1cc2)cc1c(c3)OCO1
InChI	InChI=1S/C20H20NO4/c1-21-5-4-13-7-18-19(24-10-23-18)8-14(13)16(21)6-12-2-3-17-20(15(12)9-21)25-11-22-17/h2-3,7-8,16H,4-6,9-11H2,1H3/q+1/t16-,21-/m0/s1
InChIKey	GBUUKFRQPCPYPW-KKSFZXQISA-N
Formula	C₂₀H₂₀NO₄+
HBA	4
HBD	0
MW	338.38
Rotatable Bonds	0
TPSA	36.92
LogP	2.94
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	1
Fraction CSP3	0.4
Exact Mass	338.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Glaucium arabicum	Papaveraceae	Plantae	2072396

Showing of synonyms

Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]

Pubchem: 5460426

Zinc: ZINC000255211716

Chebi: 444

Nmrshiftdb2: 60027413

Metabolights: MTBLC444

Pdb Ligand: SYT

No compound-protein relationship available.

SMILES: O1COc(c12)ccc3c2C[NH+]4C(C3)c5c(CC4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 338.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.57
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.19
Plasma Protein Binding: 70.24
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: Non-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: 14.28
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.37
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.01
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.19
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: Safe
T. Pyriformis: -3.81
Rat (Acute): 2.59
Rat (Chronic Oral): 0.72
Fathead Minnow: 4.43
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 464.89
Hydration Free Energy: -5.57
Log(D) at pH=7.4: 2.35
Log(P): -0.19
Log S: -1.18
Log(Vapor Pressure): -11.3
Melting Point: 261.84
pKa Acid: 10.7
pKa Basic: 3.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9752
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9745
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9499
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9258
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9245
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.9228
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9107
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9081
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8995
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8876
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8858
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8634
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8604
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8473
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.8442
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8441
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8402
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8402
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8302
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8114
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.8104
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.8096
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8094
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8082
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8077
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7954
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7877
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7834
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7830
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7824
S-norcoclaurine synthase	Q67A25	NCS_THLFG	Thalictrum flavum subsp. glaucum	3	0.7791
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7783
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7770
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7747
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7740
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7740
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7739
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7730
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7726
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7722
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7666
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7598
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7587
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7581
Putative cytochrome P450	Q70AS3	Q70AS3_STRPE	Streptomyces peucetius	3	0.7575
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7567
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7541
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7537
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7523
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7519
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7509
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7498
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7477
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7471
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7429
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7420
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7419
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7400
Pyruvate kinase PKM	P14618	KPYM_HUMAN	Homo sapiens	3	0.7379
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7363
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7348
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7343
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7331
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7330
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7318
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7299
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7296
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7295
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7290
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7284
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7279
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7272
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7269
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7266
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7265
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7249
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7220
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7217
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7215
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7214
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7212
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7205
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7204
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7204
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7203
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7170
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7160
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7157
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7153
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7136
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7131
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7129
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7127
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7117
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7112
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7101
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7100
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7091
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7080
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7080
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7050
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7049
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7049
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7046
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7035
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7033
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7031
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7029
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7019
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7016
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7010
Peroxisome proliferator-activated receptor alpha	Q07869	PPARA_HUMAN	Homo sapiens	2	0.7002
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	2	0.7001

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