Ancistrolikokine E2 - Compound Card

Ancistrolikokine E2

Select a section from the left sidebar

Ancistrolikokine E2

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)cc2OC)O
InChI InChI=1S/C24H25NO4/c1-12-8-16-15(6-7-18(26)24(16)20(9-12)28-4)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 LHRYTRIXHHUCIK-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
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: 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)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.760
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.380
Plasma Protein Binding
87.16
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.200
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.170
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.190
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
-14.430
Rat (Acute)
2.240
Rat (Chronic Oral)
2.440
Fathead Minnow
5.220
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
481.170
Hydration Free Energy
-6.530
Log(D) at pH=7.4
4.080
Log(P)
4.98
Log S
-6.45
Log(Vapor Pressure)
-8.11
Melting Point
185.48
pKa Acid
9.45
pKa Basic
7.34
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 0.9367
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9367
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9223
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9223
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
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9143
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9143
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9141
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9141
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8969
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8969
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8739
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8739
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8590
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8590
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8521
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8521
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8520
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8520
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8477
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8477
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8301
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8301
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8079
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8079
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8053
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8053
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8014
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8014
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8012
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8012
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7880
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7880
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7867
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7867
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7854
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7854
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7818
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7818
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7805
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7805
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7707
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7707
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7666
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7666
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7616
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7616
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7569
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7569
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7534
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7534
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7505
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7505
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7478
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7478
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7474
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7474
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7473
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7473
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7470
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7467
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7467
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7382
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7382
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7368
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7368
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7361
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7361
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7342
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7342
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7339
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7339
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7298
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7298
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7272
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7272
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7259
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7259
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7256
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7256
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7254
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7254
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7252
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7252
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7246
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7246
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7208
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7208
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7198
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7198
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7186
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7186
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7169
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7169
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7161
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7161
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7143
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7143
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7143
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7143
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7129
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7129
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7121
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7121
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7118
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7118
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7103
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7103
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7092
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7092
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7085
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7085
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7083
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7083
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7077
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7077
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7067
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7067
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7064
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7064
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7023
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7023
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7021
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7021
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7013
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7013
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7004
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7004
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7001
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7001

Download SDF