Ancistrolikokine C2 - Compound Card

Ancistrolikokine C2

Select a section from the left sidebar

Ancistrolikokine C2

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(OC)c2c(c1c1ccc(c3c1cc(C)cc3O)OC)C[C@H](N([C@@H]2C)C)C
InChI InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)20(28)11-14)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-/m1/s1
InChIKey QCRNSFIWXGLJQP-HZPDHXFCSA-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
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)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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.99
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
-1.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
74.56
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
9.830
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.650
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.300
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.820
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
Toxic
T. Pyriformis
-51.510
Rat (Acute)
2.650
Rat (Chronic Oral)
1.890
Fathead Minnow
5.470
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
471.630
Hydration Free Energy
-4.750
Log(D) at pH=7.4
4.420
Log(P)
5.01
Log S
-4.99
Log(Vapor Pressure)
-9.28
Melting Point
144.02
pKa Acid
10.18
pKa Basic
9.73
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 0.9361
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9361
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9212
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9212
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9211
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9211
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9177
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9177
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9126
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9126
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9126
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9126
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9100
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9100
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9013
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8902
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8902
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8747
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8747
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8650
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8650
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8622
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8622
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8581
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8581
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8461
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8461
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8277
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8277
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8232
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8232
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8215
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8215
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8135
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.8135
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8051
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8051
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7947
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7947
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7931
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7931
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7929
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7929
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7860
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7860
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7837
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7837
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7749
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7749
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7745
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7745
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7721
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7721
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7644
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7644
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7638
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7638
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7616
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7616
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7605
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7605
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7598
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7598
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7581
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7581
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7578
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7578
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7568
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7568
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7541
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7541
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7484
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7484
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7478
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7478
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7442
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7442
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7436
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7436
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7429
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7429
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7424
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7424
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7415
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7415
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7406
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7406
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7371
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7371
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7367
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7367
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7334
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7334
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7329
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7329
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7319
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7319
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7299
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7299
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7293
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7293
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7279
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7279
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7278
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7278
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7263
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7263
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7263
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 4 0.7263
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7238
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7238
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7226
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7226
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7225
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7225
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7210
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7210
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7209
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7209
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7187
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7187
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7160
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7160
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7157
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7157
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7143
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7143
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7136
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7136
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7131
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7131
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7111
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7111
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7110
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7110
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7103
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7103
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7102
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7102
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7096
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7096
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7055
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7055
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7055
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7055
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7049
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7049
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7043
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7043
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7015
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7015
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7014
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7014
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7008
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7008
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7007
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7007
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7006
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7006
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7003
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7003

Download SDF