Ancistrolikokine A - Compound Card

Ancistrolikokine A

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Ancistrolikokine A

Structure
Zoomed Structure
  • Family: Plantae - Ancistrocladaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Naphthylisoquinoline Alkaloid
Canonical Smiles COc1cc(O)c2c(c1c1ccc(c3c1cc(C)cc3OC)O)C[C@H](N([C@@H]2C)C)C
InChI InChI=1S/C25H29NO4/c1-13-9-17-16(7-8-19(27)25(17)21(10-13)29-5)24-18-11-14(2)26(4)15(3)23(18)20(28)12-22(24)30-6/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15-/m1/s1
InChIKey ANPZWXGVVSLGLN-HUUCEWRRSA-N
Formula C25H29NO4
HBA 5
HBD 2
MW 407.51
Rotatable Bonds 3
TPSA 62.16
LogP 5.18
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 407.21
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

  • Bringmann G, Saeb W, et al. (2003). Ancistrolikokine D, a 5,8'-coupled naphthylisoquinoline alkaloid, and related natural products from Ancistrocladus likoko. Phytochemistry,2003, 62(4), 631-636. [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: 407.51 g/mol

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Structure

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Anti-leishmanial

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.880
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
75.73
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.210
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.370
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.840
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-31.330
Rat (Acute)
2.370
Rat (Chronic Oral)
2.010
Fathead Minnow
5.030
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
469.250
Hydration Free Energy
-6.610
Log(D) at pH=7.4
4.110
Log(P)
4.74
Log S
-4.68
Log(Vapor Pressure)
-9.37
Melting Point
155.0
pKa Acid
9.63
pKa Basic
9.39
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 0.9513
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9513
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9361
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9361
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9164
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9164
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9147
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9147
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9132
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9132
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9012
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9012
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8660
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8660
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8606
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8606
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8602
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8602
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8527
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8527
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8513
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8513
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8374
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8374
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8336
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8336
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8183
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8183
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8104
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8104
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7985
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7985
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7977
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7977
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7967
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7967
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7925
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7925
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7910
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7910
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7826
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7826
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7816
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7816
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7757
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7757
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7682
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7682
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7678
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7678
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7654
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7654
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7646
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7646
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7593
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7593
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7578
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7578
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7551
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7551
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7543
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7543
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7507
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7507
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7488
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7488
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7472
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7472
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7447
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7447
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7419
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7419
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7418
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7418
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7407
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7407
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7405
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7405
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7395
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7395
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7380
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7380
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7377
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7377
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7370
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7370
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7303
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7303
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7297
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7297
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7295
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7295
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7291
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7291
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7286
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7286
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7267
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7267
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7262
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7262
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7223
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7223
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7196
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7196
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7193
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7193
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7190
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7190
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7176
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7176
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7174
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7174
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7158
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7158
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7151
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7151
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7134
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7134
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7133
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7133
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7123
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7123
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7123
Thiamine-monophosphate kinase O67883 THIL_AQUAE Aquifex aeolicus 3 0.7123
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7113
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7113
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7111
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7111
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7111
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7111
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7105
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7105
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7098
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7098
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7093
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7093
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7078
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7078
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7067
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7067
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7065
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7065
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7051
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7051
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7051
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7051
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7050
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7050
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7037
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7037
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7004
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7004
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7002
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7002

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