1,3-dimethoxy-N-methylacridone - Compound Card

1,3-dimethoxy-N-methylacridone

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1,3-dimethoxy-N-methylacridone

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1cc(OC)cc2c1c(=O)c1c(n2C)cccc1
InChI InChI=1S/C16H15NO3/c1-17-12-7-5-4-6-11(12)16(18)15-13(17)8-10(19-2)9-14(15)20-3/h4-9H,1-3H3
InChIKey WNNQYTLUXXDDQL-UHFFFAOYSA-N
Formula C16H15NO3
HBA 4
HBD 0
MW 269.3
Rotatable Bonds 2
TPSA 40.46
LogP 2.71
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 269.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Teclea gerrardii Rutaceae Plantae 1237830

Showing of synonyms

  • Waffo AF, Coombes PH, et al. (2007). Acridone and furoquinoline alkaloids from Teclea gerrardii(Rutaceae: Toddalioideae) of southern Africa. Phytochemistry, 2007, 68(5), 663–667. [View]
Pubchem: 83122
Nmrshiftdb2: 60064548

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 269.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.850
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
66.19
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
Non-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
2.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.570
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.910
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
Safe
T. Pyriformis
4.200
Rat (Acute)
2.010
Rat (Chronic Oral)
2.070
Fathead Minnow
5.040
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
409.300
Hydration Free Energy
-9.720
Log(D) at pH=7.4
1.350
Log(P)
2.41
Log S
-4.12
Log(Vapor Pressure)
-6.18
Melting Point
171.94
pKa Acid
6.9
pKa Basic
3.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9773
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9418
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9410
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9361
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9249
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9241
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9190
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9144
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9089
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9002
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8892
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8867
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8848
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8809
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8788
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8757
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8737
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8729
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8723
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8705
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8693
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8691
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8643
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8622
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8520
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8500
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8496
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8455
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8445
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8413
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8340
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8329
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8161
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8117
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8102
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8076
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8063
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8058
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7921
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7913
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7911
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7901
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7898
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7884
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7872
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7853
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7832
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7730
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7713
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7705
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7681
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7677
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7668
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7647
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7643
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7639
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7637
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7635
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7612
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7612
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7611
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7607
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7605
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7604
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7596
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7594
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7580
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7572
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7571
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7552
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7548
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7532
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7524
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7497
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7495
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7489
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7482
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7470
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7462
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7461
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7456
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7443
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7427
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7425
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7409
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7409
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7406
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7397
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7393
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7382
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7366
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7365
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7340
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7335
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7333
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7333
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7332
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7317
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7308
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7306
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7301
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7301
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7265
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7264
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7246
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7241
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7240
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7235
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7200
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7199
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7198
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7192
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7174
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7170
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7165
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7151
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7149
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7143
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7138
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7110
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7110
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7101
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7084
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7070
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7068
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7067
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7063
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7061
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7052
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 2 0.7052
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7019

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