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1-methoxycanthin-6-one
- Family: Plantae - Simaroubaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Canthinone Alkaloid
| Canonical Smiles | COc1cnc2c3c1c1ccccc1n3c(=O)cc2 |
|---|---|
| InChI | InChI=1S/C15H10N2O2/c1-19-12-8-16-10-6-7-13(18)17-11-5-3-2-4-9(11)14(12)15(10)17/h2-8H,1H3 |
| InChIKey | LEPXKGXTXIACRO-UHFFFAOYSA-N |
| Formula | C15H10N2O2 |
| HBA | 4 |
| HBD | 0 |
| MW | 250.26 |
| Rotatable Bonds | 1 |
| TPSA | 43.6 |
| LogP | 2.45 |
| Number Rings | 4 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 250.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Brucea antidysenterica | Simaroubaceae | Plantae | 459111 |
| 2 | Brucea antidysenterica | Simaroubaceae | Plantae | 459111 |
| 3 | Quassia amara | Simaroubaceae | Plantae | 43725 |
Showing of synonyms
1-methoxycanthin-6-one
1-Methoxycanthinone
60755-86-4
6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 1-methoxy-
CHEBI:66700
1-Methoxy-6H-indolo(3,2,1-de)(1,5)naphthyridin-6-one
1-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
1-Methoxy-indolo[3,2,1-de][1,5]naphthyridin-6-one
CHEMBL507610
DTXSID00209576
Q27135321
8-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
- Njar VC, Alao TO, et al. (1993). 2-Methoxycanthin-6-one: A new alkaloid from the stem wood of Quassia amara. Planta Medica, 1993,59(3), 259-261. [View]
- Makong YS, Fotso GW, et al. (2021). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae).. Natural product research,2021, 35(12), 2037-2043. [View] [PubMed]
- Makong YS, Mouthé Happi G, et al. (2019). Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules, 2019, 24(23), 4412. [View] [PubMed]
Pubchem:
483522
Cas:
60755-86-4
Chebi:
66700
Nmrshiftdb2:
60078835
Metabolights:
MTBLC66700
Chembl:
CHEMBL507610
Comptox:
DTXSID00209576
No compound-protein relationship available.
SMILES: c1cccc(c1c23)n4c2c(ccc4=O)ncc3
Level: 0
Mol. Weight: 250.26 g/mol
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.56
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.020
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.24
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.450
- Plasma Protein Binding
- 78.69
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.170
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.080
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.510
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.160
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Toxic
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 3.540
- Rat (Acute)
- 2.220
- Rat (Chronic Oral)
- 1.550
- Fathead Minnow
- 4.920
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 449.490
- Hydration Free Energy
- -11.760
- Log(D) at pH=7.4
- 2.060
- Log(P)
- 2.44
- Log S
- -4.98
- Log(Vapor Pressure)
- -6.68
- Melting Point
- 236.57
- pKa Acid
- 9.72
- pKa Basic
- 4.46
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9723 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9575 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.9323 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.9310 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.9278 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8999 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8879 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8789 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8783 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8730 |
| Pteridine reductase, putative | Q581W1 | Q581W1_TRYB2 | Trypanosoma brucei brucei | 3 | 0.8704 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8692 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8653 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8646 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.8558 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.8557 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8544 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8526 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8463 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8439 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8426 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8391 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.8368 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8360 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8347 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.8340 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8274 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.8223 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8187 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8118 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.8092 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8067 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8007 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7991 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.7978 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7952 |
| D(3) dopamine receptor | P35462 | DRD3_HUMAN | Homo sapiens | 3 | 0.7933 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 2 | 0.7925 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 2 | 0.7872 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7846 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7840 |
| Hematopoietic prostaglandin D synthase | O60760 | HPGDS_HUMAN | Homo sapiens | 3 | 0.7786 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7768 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7764 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7709 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7695 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7647 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7632 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7571 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7568 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7528 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7518 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 2 | 0.7517 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7514 |
| 2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase | Q84HC8 | NCSB1_STRCZ | Streptomyces carzinostaticus | 2 | 0.7514 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7500 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7491 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7490 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7481 |
| Prenyltransferase | Q4R2T2 | Q4R2T2_STRC1 | Streptomyces sp | 2 | 0.7481 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7479 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7454 |
| Biphenyl-2,3-diol 1,2-dioxygenase | P17297 | BPHC_PSES1 | Pseudomonas sp | 3 | 0.7446 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7439 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7431 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7429 |
| Enoyl-ACP reductase | Q9BH77 | Q9BH77_PLAFA | Plasmodium falciparum | 3 | 0.7416 |
| Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 2 | 0.7405 |
| Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial | P08559 | ODPA_HUMAN | Homo sapiens | 3 | 0.7392 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7390 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7382 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 3 | 0.7374 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7350 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7346 |
| Nucleoprotein | P33469 | NCAP_CVHOC | Human coronavirus OC43 | 3 | 0.7345 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7344 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7329 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.7324 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 2 | 0.7313 |
| Glutamate receptor 3 | P19492 | GRIA3_RAT | Rattus norvegicus | 3 | 0.7301 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7288 |
| Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 2 | 0.7261 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7245 |
| Ceramide transfer protein | Q9Y5P4 | CERT_HUMAN | Homo sapiens | 3 | 0.7245 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7243 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7228 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7225 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7201 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7194 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7187 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 2 | 0.7169 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7161 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7160 |
| Gag-Pol polyprotein | P04585 | POL_HV1H2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7152 |
| High affinity 3',5'-cyclic-AMP phosphodiesterase 7A | Q13946 | PDE7A_HUMAN | Homo sapiens | 3 | 0.7135 |
| Alpha-1-acid glycoprotein 2 | P19652 | A1AG2_HUMAN | Homo sapiens | 3 | 0.7131 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7128 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7116 |
| cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 3 | 0.7110 |
| Thymidine kinase | P0DTH5 | KITH_HHV11 | Human herpesvirus 1 | 2 | 0.7109 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 3 | 0.7089 |
| Methionine aminopeptidase | P0AE18 | MAP1_ECOLI | Escherichia coli | 2 | 0.7071 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7059 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7047 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7038 |
| Putative HMP/thiamine-binding protein YkoF | O34911 | YKOF_BACSU | Bacillus subtilis | 3 | 0.7038 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7029 |