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Ancistrolikokine F2
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinoline Alkaloid
| Canonical Smiles | COc1cc(O)c(c2c1C(=N[C@@H](C2)C)C)c1ccc(c2c1cc(C)cc2OC)OC |
|---|---|
| InChI | InChI=1S/C25H27NO4/c1-13-9-17-16(7-8-20(28-4)25(17)21(10-13)29-5)24-18-11-14(2)26-15(3)23(18)22(30-6)12-19(24)27/h7-10,12,14,27H,11H2,1-6H3/t14-/m1/s1 |
| InChIKey | CFBIKBQUHRRMOQ-CQSZACIVSA-N |
| Formula | C25H27NO4 |
| HBA | 5 |
| HBD | 1 |
| MW | 405.49 |
| Rotatable Bonds | 4 |
| TPSA | 60.28 |
| LogP | 5.3 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.32 |
| Exact Mass | 405.19 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus likoko | Ancistrocladaceae | Plantae | 714102 |
Showing of synonyms
Ancistrolikokine F2
- 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]
No compound-protein relationship available.
SMILES: c1cccc(c12)cccc2-c3cccc(c34)C=NCC4
Level: 1
Mol. Weight: 405.49 g/mol
SMILES: C1=NCCc(c12)cccc2
Level: 0
Mol. Weight: 405.49 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 405.49 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.86
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.730
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.11
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.590
- Plasma Protein Binding
- 86.72
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.670
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.590
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.120
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.460
- 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
- -27.880
- Rat (Acute)
- 2.550
- Rat (Chronic Oral)
- 2.390
- Fathead Minnow
- 5.510
- 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
- 494.800
- Hydration Free Energy
- -5.290
- Log(D) at pH=7.4
- 4.120
- Log(P)
- 5.27
- Log S
- -6.73
- Log(Vapor Pressure)
- -7.89
- Melting Point
- 165.36
- pKa Acid
- 9.92
- pKa Basic
- 7.52
| 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 | 0.9379 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9284 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.9190 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.9145 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9015 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8742 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.8683 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8514 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8288 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8113 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8100 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8099 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8080 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8066 |
| Actin-related protein 3 | P61157 | ARP3_BOVIN | Bos taurus | 4 | 0.7922 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7881 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7877 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7833 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.7785 |
| Hepatocyte growth factor receptor | P08581 | MET_HUMAN | Homo sapiens | 4 | 0.7714 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7699 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7647 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7641 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7630 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7626 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7613 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7584 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7513 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7473 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.7471 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7456 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | Q27552 | Q27552_CRYPV | Cryptosporidium parvum | 3 | 0.7450 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7428 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7427 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7388 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7374 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7329 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7320 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7317 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7312 |
| 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 | 0.7235 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7204 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7179 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7169 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7168 |
| Hematopoietic prostaglandin D synthase | O60760 | HPGDS_HUMAN | Homo sapiens | 3 | 0.7129 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7128 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7102 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7101 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7052 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7047 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7042 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7015 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7009 |