Ancistrolikokine E - Compound Card

Ancistrolikokine E

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Ancistrolikokine E

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(C)cc2c1c(O)ccc2c1c(O)cc(c2c1C[C@@H](C)N=C2C)O
InChI InChI=1S/C23H23NO4/c1-11-7-15-14(5-6-17(25)23(15)20(8-11)28-4)22-16-9-12(2)24-13(3)21(16)18(26)10-19(22)27/h5-8,10,12,25-27H,9H2,1-4H3/t12-/m1/s1
InChIKey CEKZHSNCGMTYGG-GFCCVEGCSA-N
Formula C23H23NO4
HBA 5
HBD 3
MW 377.44
Rotatable Bonds 2
TPSA 82.28
LogP 4.69
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 377.16
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

  • 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]
  • 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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 377.44 g/mol

Structure

SMILES: C1=NCCc(c12)cccc2

Level: 0

Mol. Weight: 377.44 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 377.44 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
89.39
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
4.290
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.720
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.890
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.940
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
Toxic
T. Pyriformis
-6.330
Rat (Acute)
2.180
Rat (Chronic Oral)
2.450
Fathead Minnow
4.980
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
490.420
Hydration Free Energy
-7.830
Log(D) at pH=7.4
4.000
Log(P)
4.94
Log S
-6.11
Log(Vapor Pressure)
-8.57
Melting Point
216.2
pKa Acid
8.05
pKa Basic
7.62
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 0.9370
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9370
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9210
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9210
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9167
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9145
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9145
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9142
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9142
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9030
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9030
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8584
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8584
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8547
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8547
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8522
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8522
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8506
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8506
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8468
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8468
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8265
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8265
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8143
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8143
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8065
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8065
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8036
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8036
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8036
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8036
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8010
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8010
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7991
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7991
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7885
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7885
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7878
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7878
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7837
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7837
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7665
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7665
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7640
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7640
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7569
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7569
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7552
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7552
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7548
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7548
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7496
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7496
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7490
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7490
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7419
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7419
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7413
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7413
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7407
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7407
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7398
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7398
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7380
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7380
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7351
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7351
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7330
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7330
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7314
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7314
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7235
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7235
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7223
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7223
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7200
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7200
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7199
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 5 0.7172
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 5 0.7172
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7163
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7163
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7137
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7137
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7137
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7137
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7137
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7137
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7135
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7135
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7110
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7110
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7101
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7101
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7076
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7076
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7055
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7055
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7020
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7020
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7013
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7013

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