Ancistrolikokine H2 - Compound Card

Ancistrolikokine H2

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Ancistrolikokine H2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3OC)O)C[C@@H](N([C@@H]2C)C)C
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-20(28)26(18)21(11-14)29-5)25-19-12-15(2)27(4)16(3)24(19)22(30-6)13-23(25)31-7/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16+/m0/s1
InChIKey ANXPSJUENZYMEN-JKSUJKDBSA-N
Formula C26H31NO4
HBA 5
HBD 1
MW 421.54
Rotatable Bonds 4
TPSA 51.16
LogP 5.48
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 421.23
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. (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)CNCC4

Level: 1

Mol. Weight: 421.54 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.820
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
74.04
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.020
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.280
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.930
Micronucleos
Toxic
NR-AhR
Safe
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
-52.120
Rat (Acute)
2.650
Rat (Chronic Oral)
1.830
Fathead Minnow
5.460
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
472.510
Hydration Free Energy
-4.550
Log(D) at pH=7.4
4.110
Log(P)
5.04
Log S
-4.87
Log(Vapor Pressure)
-9.29
Melting Point
143.8
pKa Acid
10.22
pKa Basic
9.73
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 0.9563
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9563
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9373
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9373
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9144
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9144
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9140
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9140
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9110
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9110
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9103
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9103
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9057
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9057
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8900
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8900
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8676
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8676
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8669
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8669
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8547
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8547
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8532
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8532
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8501
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8501
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8335
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8335
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8306
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8306
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8219
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8219
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8167
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8167
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7999
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7999
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7992
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7992
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7944
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7944
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7916
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7916
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7901
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7901
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7897
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7897
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7880
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7880
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7756
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7756
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7734
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7734
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7728
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7728
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7726
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7726
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7704
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7704
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7699
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7699
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7692
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7692
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7689
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7689
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7680
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7680
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7671
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7671
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7661
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7661
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7624
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7624
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7619
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7619
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7610
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7610
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7609
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7609
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7584
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7584
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7562
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7562
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7514
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7514
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7511
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7511
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7505
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7505
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7479
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7479
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7456
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7456
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7452
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7452
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7406
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7406
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7402
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7395
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7395
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7382
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7382
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7360
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7360
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
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7331
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7331
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7318
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7318
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7314
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7314
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7304
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7304
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7275
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7275
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7270
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7270
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7247
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7247
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7235
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7235
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7191
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7191
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7180
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7180
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7176
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7176
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7174
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7174
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7169
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7169
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7158
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7158
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
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7129
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7129
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7120
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7120
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7116
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7116
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7115
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7115
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7109
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7109
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7075
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7075
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7069
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7069
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7061
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7061
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7057
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7040
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7040
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7033
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7033
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7019
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7019
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7009
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7009
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7001
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7001

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