Ancistrolikokine H - Compound Card

Ancistrolikokine H

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Ancistrolikokine H

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+/m0/s1
InChIKey ANPZWXGVVSLGLN-LSDHHAIUSA-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

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: 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

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.0
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
75.8
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
8.240
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.270
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
9.830
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
-31.490
Rat (Acute)
2.360
Rat (Chronic Oral)
2.020
Fathead Minnow
5.000
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
469.570
Hydration Free Energy
-6.620
Log(D) at pH=7.4
4.040
Log(P)
4.73
Log S
-4.69
Log(Vapor Pressure)
-9.38
Melting Point
153.56
pKa Acid
9.63
pKa Basic
9.36
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 0.9538
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9538
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9200
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9200
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9157
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9157
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9108
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9108
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9054
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9054
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8995
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8995
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8800
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8800
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8706
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.8706
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8583
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8583
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8561
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8561
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8553
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8553
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8527
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8527
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8093
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8093
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8073
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8073
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8030
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7970
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7970
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7968
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7968
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7940
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7940
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7886
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7886
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7876
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7876
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7805
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7805
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7710
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7710
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7701
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.7701
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7681
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7666
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7666
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7657
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7657
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7635
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 4 0.7635
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7620
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7620
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7589
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7589
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7560
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7560
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7535
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7535
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7530
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7530
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7514
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7514
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7497
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7497
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7481
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7481
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7474
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7474
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7460
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7460
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7452
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7452
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7450
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7450
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7446
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7446
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7412
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7412
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7408
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7408
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7400
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7400
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7391
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7391
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7306
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7306
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7277
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7277
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7274
Bifunctional dihydrofolate reductase-thymidylate synthase Q27552 Q27552_CRYPV Cryptosporidium parvum 3 0.7274
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7259
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7259
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7256
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7256
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7226
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7226
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7214
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7214
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7197
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7197
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7190
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7190
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7189
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7189
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7173
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7173
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7172
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7172
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7167
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7167
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7163
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7163
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7159
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7159
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7157
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7157
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7136
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7136
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7124
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7124
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7109
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7109
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7100
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7100
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7076
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7076
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7065
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7065
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7057
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7037
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7037
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7035
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7035
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7027
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7027
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7022
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7022
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7020
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7020
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
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7004
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7004
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7000
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7000
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7000
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7000

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