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Coptisine

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

Canonical Smiles	C1Oc2c(O1)cc1c(c2)CC[n+]2c1cc1ccc3c(c1c2)OCO3
InChI	InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1
InChIKey	XYHOBCMEDLZUMP-UHFFFAOYSA-N
Formula	C₁₉H₁₄NO₄+
HBA	4
HBD	0
MW	320.32
Rotatable Bonds	0
TPSA	40.8
LogP	2.81
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	1
Fraction CSP3	0.21
Exact Mass	320.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fumaria parviflora	Fumariaceae	Plantae	1464625
2	Fumaria parviflora	Papaveraceae	Plantae	1464625

Showing of synonyms

Elsaid M.B, Elnaggar D.M, et al. (2022). Production of isoquinoline alkaloids from the in vitro conserved Fumaria parviflora and their in vitro wound healing activity. Natural product research, 2022, 36(10), 2575-2579. [View] [PubMed]

Pubchem: 72322

Cas: 3486-66-6

Gnps: CCMSLIB00006438084

Zinc: ZINC000001709414

Kegg Ligand: C16938

Chebi: 67862

Nmrshiftdb2: 60026245

Metabolights: MTBLC67862

Chembl: CHEMBL362071

Comptox: DTXSID10188404

Pdb Ligand: KPT

Bindingdb: 50030257

CPRiL: 60664

SMILES: O1COc(c12)ccc3c2c[n+]4c(c3)c5c(CC4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 320.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.07
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.4
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.04
Plasma Protein Binding: 64.54
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: Non-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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.06
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.95
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 10.05
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: -6.06
Rat (Acute): 2.39
Rat (Chronic Oral): 0.78
Fathead Minnow: 5.1
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 458.08
Hydration Free Energy: -8.11
Log(D) at pH=7.4: 2.72
Log(P): 0.5
Log S: -2.46
Log(Vapor Pressure): -9.97
Melting Point: 239.86
pKa Acid: 11.64
pKa Basic: 2.06

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9813
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9666
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.9446
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9438
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9384
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.9371
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9363
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.9143
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9032
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8963
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8948
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8787
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8766
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8707
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8632
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8620
S-norcoclaurine synthase	Q67A25	NCS_THLFG	Thalictrum flavum subsp. glaucum	3	0.8596
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8587
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8399
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8274
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8182
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8162
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8077
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.8061
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.8049
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8018
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8016
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7997
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7988
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7971
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7967
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7932
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7922
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7917
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7913
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7900
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7878
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7856
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7842
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7796
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7791
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7782
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7767
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7762
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7761
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7743
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7743
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7738
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7737
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7703
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7683
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7656
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	2	0.7655
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7647
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7606
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7601
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7599
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7565
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7540
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7537
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7535
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7528
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7499
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7495
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7494
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7482
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7472
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7470
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7460
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7458
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	3	0.7457
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7449
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7422
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7421
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7417
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7411
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7377
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7374
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7370
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7367
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7354
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7346
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7345
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7331
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7328
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7324
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	2	0.7322
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7321
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7320
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7305
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7301
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7294
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7291
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7286
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7281
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7278
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	2	0.7277
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7255
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	2	0.7253
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7252
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7249
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	3	0.7228
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7218
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7212
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7208
Poly [ADP-ribose] polymerase 1	P26446	PARP1_CHICK	Gallus gallus	4	0.7201
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7198
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7194
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7193
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7184
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7178
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7176
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7171
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7166
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7160
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7158
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7155
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7139
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7129
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7123
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7121
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7120
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7106
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7103
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7099
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7087
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.7084
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7083
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7083
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7079
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7078
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7075
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7063
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7041
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7035
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7035
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7026
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7026
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	2	0.7020
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7013
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	2	0.7012
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7011
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7005

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