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Mbandakamine E
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1cc(O)c(c2c1C(C)N[C@@H](C2)C)c1cc(c2c(C)cc(c3c2c(ccc3OC)c2c(O)cc(c3c2C[C@@H](C)N([C@H]3C)C)OC)O)c(c2c1cc(C)cc2OC)O |
|---|---|
| InChI | InChI=1S/C49H54N2O8/c1-22-14-29-30(45-31-17-24(3)50-26(5)42(31)39(58-10)20-36(45)54)19-33(49(55)46(29)38(15-22)57-9)41-23(2)16-34(52)48-37(56-8)13-12-28(47(41)48)44-32-18-25(4)51(7)27(6)43(32)40(59-11)21-35(44)53/h12-16,19-21,24-27,50,52-55H,17-18H2,1-11H3/t24-,25-,26?,27+/m1/s1 |
| InChIKey | MPLQOMZYFMFMIU-GWDBROLASA-N |
| Formula | C49H54N2O8 |
| HBA | 10 |
| HBD | 5 |
| MW | 798.98 |
| Rotatable Bonds | 7 |
| TPSA | 133.11 |
| LogP | 10.0 |
| Number Rings | 8 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 59 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.35 |
| Exact Mass | 798.39 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus ealaensis | Ancistrocladaceae | Plantae | 714098 |
| 2 | Ancistrocladus ealaensis | Ancistrocladaceae | Plantae | 714098 |
Showing of synonyms
Mbandakamine E
- Tshitenge DT, Bruhn T, et al. (2019). An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ealaensis.. Scientific reports,2019, 9(1), 9812. [View] [PubMed]
- Tshitenge DT, Feineis D, et al. (2018). Mbandakamine-Type Naphthylisoquinoline Dimers and Related Alkaloids from the Central African Liana Ancistrocladus ealaensis with Antiparasitic and Antileukemic Activities.. Journal of natural products,2018, 81(4), 918-933. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CNCc(c12)cccc2-c3cccc(c34)cccc4-c(cc(c56)cccc6)cc5-c7cccc(c78)CNCC8
Level: 3
Mol. Weight: 798.98 g/mol
SMILES: c1cccc(c12)cccc2-c(cc(c34)cccc4)cc3-c5cccc(c56)CNCC6
Level: 2
Mol. Weight: 798.98 g/mol
SMILES: c1cccc(c12)ccc(c2)-c3cccc(c34)cccc4-c5cccc(c56)CNCC6
Level: 2
Mol. Weight: 798.98 g/mol
SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4
Level: 1
Mol. Weight: 798.98 g/mol
SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)cccc4
Level: 1
Mol. Weight: 798.98 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 798.98 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 798.98 g/mol
Antileukemia
Antiparasitic
Absorption
- Caco-2 (logPapp)
- -5.74
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 211.470
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 28421.49
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.310
- Plasma Protein Binding
- 71.23
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 7.390
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -661.560
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.070
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.140
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -51579801.600
- Rat (Acute)
- 2.400
- Rat (Chronic Oral)
- 2.690
- Fathead Minnow
- 65114.280
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 5796228.500
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- 6.240
- Log(P)
- 8.03
- Log S
- -7.43
- Log(Vapor Pressure)
- -190809.78
- Melting Point
- 203.66
- pKa Acid
- -1350.82
- pKa Basic
- 10.41
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8465 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.8287 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8263 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8110 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.8091 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.7657 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7598 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7466 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7361 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7297 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7242 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7219 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7185 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7181 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 3 | 0.7066 |
| Aldo-keto reductase family 1 member B1 | P80276 | ALDR_PIG | Sus scrofa | 3 | 0.7002 |