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Ancistrocladisine B
- Family: Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1cc2C[C@H](C)N[C@@H](c2c(c1c1c(C)cc(c2c1cccc2OC)OC)O)C |
|---|---|
| InChI | InChI=1S/C25H29NO4/c1-13-10-19(29-5)23-17(8-7-9-18(23)28-4)21(13)24-20(30-6)12-16-11-14(2)26-15(3)22(16)25(24)27/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15+/m0/s1 |
| InChIKey | XJKBCFDZMXLQGI-LSDHHAIUSA-N |
| Formula | C25H29NO4 |
| HBA | 5 |
| HBD | 2 |
| MW | 407.51 |
| Rotatable Bonds | 4 |
| TPSA | 59.95 |
| LogP | 5.14 |
| 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 ileboensis | Ancistrocladaceae | Plantae | 1367080 |
Showing of synonyms
Ancistrocladisine B
- Li J, Seupel R, et al. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese Liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of natural products,2017, 80(2), 443-458. [View] [PubMed]
No compound-protein relationship available.
SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4
Level: 1
Mol. Weight: 259.35 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 133.19 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 128.17 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -5.04
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.220
- Plasma Protein Binding
- 78.69
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-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
- 8.580
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.530
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.090
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.530
- 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
- Safe
- T. Pyriformis
- -34.430
- Rat (Acute)
- 2.520
- Rat (Chronic Oral)
- 2.110
- Fathead Minnow
- 5.220
- 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
- 454.960
- Hydration Free Energy
- -5.690
- Log(D) at pH=7.4
- 4.180
- Log(P)
- 4.04
- Log S
- -4.49
- Log(Vapor Pressure)
- -8.97
- Melting Point
- 156.04
- pKa Acid
- 10.02
- pKa Basic
- 9.71
| 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 | 0.9490 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.9306 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.9218 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8964 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8934 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8804 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.8471 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8443 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.8262 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8247 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.8206 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.8203 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8147 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.8000 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7967 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7827 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7804 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7760 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7750 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7748 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7664 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7635 |
| Glycylpeptide N-tetradecanoyltransferase | Q4Q5S8 | Q4Q5S8_LEIMA | Leishmania major | 3 | 0.7612 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7607 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7606 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7521 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.7498 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 3 | 0.7468 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7404 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7403 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7363 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7340 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7297 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7263 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7256 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7248 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7218 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7208 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7201 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7186 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7149 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7129 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7113 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7075 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7063 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7020 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7005 |
| Cytochrome P450 2C8 | P10632 | CP2C8_HUMAN | Homo sapiens | 3 | 0.7002 |