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Ancistrolikokine J2

Family: Plantae - Ancistrocladaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Quinoline Alkaloid

Canonical Smiles	COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3OC)O)cc(nc2C)C
InChI	InChI=1S/C25H25NO4/c1-13-9-17-16(7-8-19(27)25(17)20(10-13)28-4)24-18-11-14(2)26-15(3)23(18)21(29-5)12-22(24)30-6/h7-12,27H,1-6H3
InChIKey	AVRKHQXNNYLIGF-UHFFFAOYSA-N
Formula	C₂₅H₂₅NO₄
HBA	5
HBD	1
MW	403.48
Rotatable Bonds	4
TPSA	60.81
LogP	5.71
Number Rings	4
Number Aromatic Rings	4
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	403.18
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus likoko	Ancistrocladaceae	Plantae	714102

Showing of synonyms

Fayez S, Feineis D, et al. (2018). Ancistrolikokine I and further 5,8′-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko and their cytotoxic activities against drug-sensitive and multidrug resistant human leukemia cells.. Fitoterapia,2018, 129, 114-125. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c3cccc(c34)cncc4

Level: 1

Mol. Weight: 403.48 g/mol

SMILES: c1cncc(c12)cccc2

Level: 0

Mol. Weight: 403.48 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 403.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.79
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.800
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.36

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.800
Plasma Protein Binding: 89.69
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: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.190
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.870
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.200
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.120
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: -27.200
Rat (Acute): 2.760
Rat (Chronic Oral): 2.310
Fathead Minnow: 6.020
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 517.260
Hydration Free Energy: -5.780
Log(D) at pH=7.4: 4.020
Log(P): 5.38
Log S: -6.57
Log(Vapor Pressure): -8.52
Melting Point: 184.24
pKa Acid: 10.38
pKa Basic: 6.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9445
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9165
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9141
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9099
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9078
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8746
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.8698
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8531
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8514
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8476
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8475
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8372
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8259
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8219
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8122
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8055
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8039
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8037
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7928
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7842
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7775
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7734
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7695
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	4	0.7671
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7619
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7550
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7510
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7468
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7461
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7453
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7414
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7391
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7387
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27552	Q27552_CRYPV	Cryptosporidium parvum	3	0.7385
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7376
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7332
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7309
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	4	0.7295
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7294
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7289
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7277
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7268
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.7265
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7231
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7230
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7229
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7185
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7175
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7147
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7146
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7136
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7135
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7133
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7078
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7070
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7046
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7028
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	3	0.7024
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7013

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