1,11-dimethoxycanthin-6-one - Compound Card

1,11-dimethoxycanthin-6-one

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1,11-dimethoxycanthin-6-one

Structure
Zoomed Structure
  • Family: Plantae - Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Canthinone Alkaloid
Canonical Smiles COc1cccc2c1c1c(OC)cnc3c1n2c(=O)cc3
InChI InChI=1S/C16H12N2O3/c1-20-11-5-3-4-10-14(11)15-12(21-2)8-17-9-6-7-13(19)18(10)16(9)15/h3-8H,1-2H3
InChIKey VGXICZIFUHMPMS-UHFFFAOYSA-N
Formula C16H12N2O3
HBA 5
HBD 0
MW 280.28
Rotatable Bonds 2
TPSA 52.83
LogP 2.46
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 280.08
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

  • 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: 190613

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)n4c2c(ccc4=O)ncc3

Level: 0

Mol. Weight: 280.28 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.080
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.420
Plasma Protein Binding
78.78
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
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
1.370
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.470
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.040
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
3.590
Rat (Acute)
2.160
Rat (Chronic Oral)
1.540
Fathead Minnow
4.900
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
479.340
Hydration Free Energy
-12.640
Log(D) at pH=7.4
2.380
Log(P)
2.52
Log S
-5.06
Log(Vapor Pressure)
-6.89
Melting Point
230.89
pKa Acid
10.37
pKa Basic
5.1
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 0.9554
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9507
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.9479
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9473
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.9374
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9226
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9064
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9002
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8982
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8963
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8833
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8632
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8571
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8557
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8393
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8371
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8219
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8209
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8186
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8182
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8173
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8161
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8147
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8079
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8050
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8044
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7992
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7961
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7952
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7943
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7866
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7860
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7849
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7821
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7819
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7810
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7793
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7773
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7773
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7763
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7761
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7731
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7716
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7695
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7685
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7673
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7619
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 3 0.7617
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7604
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7603
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7567
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7563
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7525
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7517
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7497
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7483
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7438
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7433
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7432
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7418
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7387
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7368
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7360
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7338
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7266
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7258
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7254
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7249
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7247
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7245
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7243
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7222
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7204
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7202
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7196
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7181
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7171
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7164
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7163
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7160
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7153
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7144
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7140
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7133
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7121
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7115
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7099
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7083
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7058
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7045
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7020
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7016
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7004

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