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Ancistrobrevine J
- Family: Plantae - Ancistrocladaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid
| Canonical Smiles | COc1cc2C[C@@H](C)N=C(c2c(c1c1ccc(c2c1cc(C)cc2OC)OC)O)C |
|---|---|
| InChI | InChI=1S/C25H27NO4/c1-13-9-18-17(7-8-19(28-4)23(18)20(10-13)29-5)24-21(30-6)12-16-11-14(2)26-15(3)22(16)25(24)27/h7-10,12,14,27H,11H2,1-6H3/t14-/m1/s1 |
| InChIKey | BVQLTRHNRBNBPY-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 abbreviatus | Ancistrocladaceae | Plantae | 122295 |
Showing of synonyms
Ancistrobrevine J
- Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]
No compound-protein relationship available.
SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCN=C4
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
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.91
- 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
- -1.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.520
- Plasma Protein Binding
- 86.29
- 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
- 6.360
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.760
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.140
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.430
- 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
- -27.840
- Rat (Acute)
- 2.630
- Rat (Chronic Oral)
- 2.430
- Fathead Minnow
- 5.490
- 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
- 493.790
- Hydration Free Energy
- -5.210
- Log(D) at pH=7.4
- 3.950
- Log(P)
- 5.17
- Log S
- -6.56
- Log(Vapor Pressure)
- -7.92
- Melting Point
- 158.69
- pKa Acid
- 9.62
- pKa Basic
- 7.81
| 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 | 0.9156 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.9125 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.8905 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8904 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.8775 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8497 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8477 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.8434 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8354 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.8304 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8130 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.8123 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8107 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8093 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.8080 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.8000 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7978 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7976 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7950 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7940 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 3 | 0.7938 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7925 |
| Endolysin | P00720 | ENLYS_BPT4 | Enterobacteria phage T4 | 3 | 0.7913 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7902 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7886 |
| Transthyretin | Q9PTT3 | Q9PTT3_SPAAU | Sparus aurata | 3 | 0.7766 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7752 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.7707 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7666 |
| Serine/threonine-protein kinase PLK2 | Q9NYY3 | PLK2_HUMAN | Homo sapiens | 3 | 0.7660 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7613 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7611 |
| TetR family transcriptional regulator | Q58L87 | Q58L87_MYCSM | Mycolicibacterium smegmatis | 3 | 0.7609 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7589 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7577 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7550 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7537 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7500 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7480 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7467 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7416 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7411 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.7391 |
| HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7383 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7357 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7356 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7316 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7291 |
| Thyroxine-binding globulin | P05543 | THBG_HUMAN | Homo sapiens | 3 | 0.7271 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7235 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7212 |
| Putative HMP/thiamine-binding protein YkoF | O34911 | YKOF_BACSU | Bacillus subtilis | 3 | 0.7207 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7199 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7182 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7180 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7172 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7159 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7141 |
| Cytochrome P450 2C8 | P10632 | CP2C8_HUMAN | Homo sapiens | 3 | 0.7140 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7130 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7096 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.7094 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7076 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7065 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 4 | 0.7059 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7058 |
| 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 | O50008 | METE1_ARATH | Arabidopsis thaliana | 2 | 0.7047 |
| Granule-bound starch synthase 1, chloroplastic/amyloplastic | Q0DEV5 | SSG1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7046 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7011 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7002 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7001 |