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Dioncophylline D2
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1ccc(c2c1c(OC)cc(c2)C)c1ccc2c(c1O)[C@@H](C)N([C@H](C2)C)C |
|---|---|
| InChI | InChI=1S/C25H29NO3/c1-14-11-20-18(9-10-21(28-5)24(20)22(12-14)29-6)19-8-7-17-13-15(2)26(4)16(3)23(17)25(19)27/h7-12,15-16,27H,13H2,1-6H3/t15-,16+/m0/s1 |
| InChIKey | MYPHOFQPUOJYOZ-JKSUJKDBSA-N |
| Formula | C25H29NO3 |
| HBA | 4 |
| HBD | 1 |
| MW | 391.51 |
| Rotatable Bonds | 3 |
| TPSA | 41.93 |
| LogP | 5.48 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.36 |
| Exact Mass | 391.21 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ancistrocladus ileboensis | Ancistrocladaceae | Plantae | 1367080 |
Showing of synonyms
Dioncophylline D2
- 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: 391.51 g/mol
SMILES: C1CNCc(c12)cccc2
Level: 0
Mol. Weight: 391.51 g/mol
SMILES: c1cccc(c12)cccc2
Level: 0
Mol. Weight: 391.51 g/mol
Antimalarial
Absorption
- Caco-2 (logPapp)
- -5.09
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.820
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -0.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.150
- Plasma Protein Binding
- 81.92
- 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
- 7.530
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 2.620
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.740
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.020
- 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
- -20.330
- Rat (Acute)
- 2.810
- Rat (Chronic Oral)
- 1.900
- Fathead Minnow
- 5.080
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 451.010
- Hydration Free Energy
- -6.440
- Log(D) at pH=7.4
- 3.860
- Log(P)
- 4.76
- Log S
- -4.18
- Log(Vapor Pressure)
- -8.98
- Melting Point
- 144.43
- pKa Acid
- 9.86
- pKa Basic
- 9.53
| 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 | 0.9470 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9117 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.9071 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.9061 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9051 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.8942 |
| 11-beta-hydroxysteroid dehydrogenase 1 | Q6QLL4 | DHI1_CAVPO | Cavia porcellus | 3 | 0.8688 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.8590 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8533 |
| Bromodomain testis-specific protein | Q58F21 | BRDT_HUMAN | Homo sapiens | 3 | 0.8526 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8476 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8465 |
| Transthyretin | Q9PTT3 | Q9PTT3_SPAAU | Sparus aurata | 3 | 0.8421 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8388 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8314 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8278 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.8196 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.8158 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8137 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.8134 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8106 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.8090 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8048 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.8005 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.7996 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7941 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7869 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7799 |
| Tubulin alpha chain | D0VWZ0 | D0VWZ0_SHEEP | Ovis aries | 3 | 0.7746 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7668 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7625 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7620 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7617 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7608 |
| Endoplasmin | P14625 | ENPL_HUMAN | Homo sapiens | 3 | 0.7584 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.7581 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7574 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7550 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7533 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7523 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7504 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7474 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7417 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7416 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7410 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7408 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7396 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7356 |
| HLA class I histocompatibility antigen, B alpha chain | P01889 | HLAB_HUMAN | Homo sapiens | 3 | 0.7353 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7339 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.7330 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7329 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7327 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 4 | 0.7293 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7267 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7249 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7243 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7232 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7210 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.7205 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7141 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 3 | 0.7136 |
| Granule-bound starch synthase 1, chloroplastic/amyloplastic | Q0DEV5 | SSG1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7133 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7123 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7122 |
| Mitogen-activated protein kinase 1 | P63086 | MK01_RAT | Rattus norvegicus | 3 | 0.7101 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7100 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7077 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7075 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7063 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7058 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7052 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7047 |