Ancistrolikokine F - Compound Card

Ancistrolikokine F

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Ancistrolikokine F

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c(c2c1C(=N[C@@H](C2)C)C)c1ccc(c2c1cc(C)cc2O)OC
InChI InChI=1S/C24H25NO4/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/h6-9,11,13,26-27H,10H2,1-5H3/t13-/m1/s1
InChIKey CAGBCZAJHUAFBK-CYBMUJFWSA-N
Formula C24H25NO4
HBA 5
HBD 2
MW 391.47
Rotatable Bonds 3
TPSA 71.28
LogP 5.0
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 391.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ancistrocladus likoko Ancistrocladaceae Plantae 714102

Showing of synonyms

  • 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: 163000264
Nmrshiftdb2: 60049025

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4

Level: 1

Mol. Weight: 391.47 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 391.47 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.400
Plasma Protein Binding
87.96
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
5.940
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.230
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.110
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
-14.240
Rat (Acute)
2.240
Rat (Chronic Oral)
2.440
Fathead Minnow
5.210
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
478.510
Hydration Free Energy
-6.690
Log(D) at pH=7.4
4.340
Log(P)
4.92
Log S
-6.64
Log(Vapor Pressure)
-8.14
Melting Point
183.41
pKa Acid
9.29
pKa Basic
7.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9237
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9237
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9186
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9186
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9145
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9145
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9094
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9094
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8995
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8995
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8984
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8984
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8973
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8973
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8740
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8740
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8734
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8734
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8409
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8409
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8405
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8405
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8130
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8130
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8121
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8121
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8081
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8081
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8039
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8039
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8030
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8030
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7917
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7917
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7897
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7897
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7870
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7870
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7772
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7772
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7719
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7719
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7718
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7718
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7647
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7647
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7634
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7634
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7614
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7614
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7489
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7489
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7450
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7450
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7448
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7448
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7446
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7446
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7428
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7428
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7423
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7423
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7374
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7374
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7312
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7312
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7285
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7272
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7272
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7270
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7270
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7266
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7266
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7249
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7249
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7232
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7232
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7219
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7219
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7184
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7184
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7149
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7149
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7148
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7148
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7123
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7123
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7121
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7121
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7109
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7109
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7099
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7099
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7074
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7074
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7071
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7071
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7070
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7070
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7056
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7056
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7054
Nicotinamide riboside kinase 1 Q9NWW6 NRK1_HUMAN Homo sapiens 4 0.7054
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7053
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7053
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7044
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7044
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7032
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7032
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7025
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7025
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7014
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7014

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