ANPDB

Select a section from the left sidebar

Ancistrolikokine B

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

Canonical Smiles	COc1cc(O)c(c2c1[C@H](C)N[C@@H](C2)C)c1ccc(c2c1cc(C)cc2O)OC
InChI	InChI=1S/C24H27NO4/c1-12-8-16-15(6-7-20(28-4)24(16)18(26)9-12)23-17-10-13(2)25-14(3)22(17)21(29-5)11-19(23)27/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14+/m1/s1
InChIKey	AFHOBLZGERHVHS-KGLIPLIRSA-N
Formula	C₂₄H₂₇NO₄
HBA	5
HBD	3
MW	393.48
Rotatable Bonds	3
TPSA	70.95
LogP	4.84
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	393.19
Number of Lipinski Rule Violations	0

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

Showing of synonyms

Bringmann G, Saeb W, et al. (2003). Ancistrolikokine D, a 5,8'-coupled naphthylisoquinoline alkaloid, and related natural products from Ancistrocladus likoko. Phytochemistry,2003, 62(4), 631-636. [View] [PubMed]
Fayez S, Feineis D, et al. (2017). Ancistrolikokines E-H and related 5,8'-coupled naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus likoko with antiausterity activities against PANC-1 human pancreatic cancer cells.. RSC Adv., 2017,7, 53740-53751. [View]

Pubchem: 10000664

Cas: 297749-37-2

Zinc: ZINC000033663659

Nmrshiftdb2: 80000403

Chembl: CHEMBL520553

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 393.48 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp): -5.1
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.940
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.160
Plasma Protein Binding: 76.82
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.240
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.520
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.190
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.320
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: -20.450
Rat (Acute): 2.290
Rat (Chronic Oral): 2.200
Fathead Minnow: 4.970
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 462.810
Hydration Free Energy: -8.080
Log(D) at pH=7.4: 4.530
Log(P): 3.96
Log S: -5.03
Log(Vapor Pressure): -8.64
Melting Point: 159.66
pKa Acid: 9.56
pKa Basic: 9.12

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9253
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9253
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9098
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9098
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9092
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9092
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9084
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9084
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9057
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9057
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9001
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.9001
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8861
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8861
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8742
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8742
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8697
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8697
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8552
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8552
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8479
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8479
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8131
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8131
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8075
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8075
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8034
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8034
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8018
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8018
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7984
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7984
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7832
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7832
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7740
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7740
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7619
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7619
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7608
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7608
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7533
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7533
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7515
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7515
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7491
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7491
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7488
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7488
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7421
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7421
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7417
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7417
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7391
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7391
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7385
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7385
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7356
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7356
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7347
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7347
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7287
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7287
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7282
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7282
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7281
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7281
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7273
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7273
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7259
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7259
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7227
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7227
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7222
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7222
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7196
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7196
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7185
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7185
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7166
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7166
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7158
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7158
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7136
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7136
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7131
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7131
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7113
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7113
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7090
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7090
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7079
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7079
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7025
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7025
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7017
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7017
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7012
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7012

Download SDF