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8-oxocoptisine

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

Canonical Smiles	O=c1c2c(ccc3c2OCO3)cc2n1CCc1c2cc2c(c1)OCO2
InChI	InChI=1S/C19H13NO5/c21-19-17-11(1-2-14-18(17)25-9-22-14)5-13-12-7-16-15(23-8-24-16)6-10(12)3-4-20(13)19/h1-2,5-7H,3-4,8-9H2
InChIKey	UCAFJBSQKXVPDX-UHFFFAOYSA-N
Formula	C₁₉H₁₃NO₅
HBA	6
HBD	0
MW	335.32
Rotatable Bonds	0
TPSA	58.92
LogP	2.68
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	335.08
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: 5245667

Cas: 19716-61-1

Zinc: ZINC000013459011

Nmrshiftdb2: 60033248

Chembl: CHEMBL3612189

Bindingdb: 50131223

No compound-protein relationship available.

SMILES: O1COc(c12)ccc3c2c(=O)n4c(c3)c5c(CC4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 335.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.03
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.380
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.590
Plasma Protein Binding: 81.89
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: 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: 12.660
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.040
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.110
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.410
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -4.620
Rat (Acute): 1.950
Rat (Chronic Oral): 0.830
Fathead Minnow: 5.010
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 518.070
Hydration Free Energy: -6.460
Log(D) at pH=7.4: 2.670
Log(P): 3.66
Log S: -5.31
Log(Vapor Pressure): -11.44
Melting Point: 295.1
pKa Acid: 10.33
pKa Basic: 3.87

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	0.9725
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9373
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9270
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9195
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9175
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9102
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8863
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8824
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8776
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8741
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8730
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8714
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8701
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8663
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8637
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8544
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8543
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8522
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8501
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8435
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8406
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8342
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8311
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8292
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8196
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8157
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8147
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8068
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8066
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	4	0.8043
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.8036
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7988
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7984
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7944
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7929
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7920
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7862
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7859
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7837
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7801
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7793
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7755
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7749
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7748
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7726
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7724
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7663
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7649
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7647
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7647
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7640
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7606
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7603
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7602
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7597
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7595
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7590
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7584
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7582
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7582
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7572
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7561
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7558
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7549
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7547
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7547
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7515
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7502
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7491
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7474
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.7454
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7439
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7439
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7437
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7433
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7427
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7411
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7411
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7396
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7380
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7372
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7363
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7351
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7334
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7324
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7321
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7320
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7316
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7312
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7299
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7287
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7252
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7250
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7241
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7231
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7230
Lanosterol 14-alpha demethylase	A6ZSR0	A6ZSR0_YEAS7	Saccharomyces cerevisiae	3	0.7213
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7198
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7194
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7176
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7165
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7157
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7139
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7137
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7135
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7114
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7106
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7104
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7101
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7096
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7082
Poly [ADP-ribose] polymerase 1	P26446	PARP1_CHICK	Gallus gallus	4	0.7067
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7052
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7052
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7040
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7032
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7023
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7023
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	4	0.7020
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7001
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7001

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