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4-(3′,3′-dimethylallyloxy)-3-(3′′,3′′-dimethylallyl)-2(1H)-quinolone
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Quinoline Alkaloid
| Canonical Smiles | CC(CCOC1C(CC=C(C)C)C(=O)Nc2c1cccc2)C |
|---|---|
| InChI | InChI=1S/C19H27NO2/c1-13(2)9-10-16-18(22-12-11-14(3)4)15-7-5-6-8-17(15)20-19(16)21/h5-9,14,16,18H,10-12H2,1-4H3,(H,20,21) |
| InChIKey | DGMQXPNGXNZFBA-UHFFFAOYSA-N |
| Formula | C19H27NO2 |
| HBA | 2 |
| HBD | 1 |
| MW | 301.43 |
| Rotatable Bonds | 6 |
| TPSA | 38.33 |
| LogP | 4.72 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 301.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Haplophyllum tuberculatum | Rutaceae | Plantae | 452784 |
Showing of synonyms
4-(3′,3′-dimethylallyloxy)-3-(3′′,3′′-dimethylallyl)-2(1H)-quinolone
- M. Sheriha G, Abouamer K, et al. (1987). Quinoline alkaloids and cytotoxic lignans from Haplophyllum tuberculatum. Phytochemistry, 1987, 26(12), 3339-3341. [View]
No compound-protein relationship available.
SMILES: C1CC(=O)Nc(c12)cccc2
Level: 0
Mol. Weight: 301.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.56
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.39
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.04
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.02
- Plasma Protein Binding
- 43.9
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-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
- 7.58
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.54
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.01
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.9
- Micronucleos
- Safe
- NR-AhR
- Safe
- 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
- 2.8
- Rat (Acute)
- 1.95
- Rat (Chronic Oral)
- 1.92
- Fathead Minnow
- 4.42
- 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
- 362.74
- Hydration Free Energy
- -7.4
- Log(D) at pH=7.4
- 3.58
- Log(P)
- 5.07
- Log S
- -4.96
- Log(Vapor Pressure)
- -5.88
- Melting Point
- 84.61
- pKa Acid
- 10.6
- pKa Basic
- 6.73
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8967 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8910 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 3 | 0.8885 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8479 |
| Epoxide hydrolase | Q41415 | Q41415_SOLTU | Solanum tuberosum | 3 | 0.8423 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8419 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8402 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8331 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8149 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8016 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7980 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7974 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7917 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7877 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7872 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7847 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7812 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.7764 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7665 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7657 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7647 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.7643 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7577 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7575 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7569 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7569 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7556 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7538 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7535 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7529 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7524 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7517 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7483 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7454 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7425 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 2 | 0.7401 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7389 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7383 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 2 | 0.7360 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7331 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7283 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7282 |
| Matrix metalloproteinase-20 | O60882 | MMP20_HUMAN | Homo sapiens | 3 | 0.7281 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 2 | 0.7272 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7258 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 2 | 0.7247 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7231 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7214 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7211 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7201 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7184 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7167 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7162 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7158 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7144 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7137 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7130 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7120 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7099 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7096 |
| Histone deacetylase-like amidohydrolase | Q70I53 | HDAH_ALCSD | Alcaligenes sp.) | 2 | 0.7092 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7076 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 2 | 0.7075 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7059 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7056 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7052 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7051 |
| Alcohol dehydrogenase 1C | P00326 | ADH1G_HUMAN | Homo sapiens | 2 | 0.7032 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7021 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7019 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7017 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7017 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7015 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7014 |