1-hydroxy-3-methoxy-10-methyl-9-acridone - Compound Card

1-hydroxy-3-methoxy-10-methyl-9-acridone

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1-hydroxy-3-methoxy-10-methyl-9-acridone

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridine Alkaloid
Canonical Smiles COc1cc(O)c2c(c1)n(C)c1c(c2=O)cccc1
InChI InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3
InChIKey OCUBFJMZYYIVBO-UHFFFAOYSA-N
Formula C15H13NO3
HBA 4
HBD 1
MW 255.27
Rotatable Bonds 1
TPSA 51.46
LogP 2.41
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 255.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zanthoxylum leprieurii Rutaceae Plantae 992815

Showing of synonyms

  • Ngoumfo RM, Jouda JB, et al. (2010). In vitro cytotoxic activity of isolated acridones alkaloids from Zanthoxylum leprieurii Guill. et Perr.. Bioorganic & medicinal chemistry,2010, 18(10), 3601-3605. [View] [PubMed]
Pubchem: 5377412
Chebi: 173801
Nmrshiftdb2: 60023898

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 255.27 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.140
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.250
Plasma Protein Binding
63.35
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
1.440
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.440
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.040
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
4.350
Rat (Acute)
2.110
Rat (Chronic Oral)
2.310
Fathead Minnow
4.760
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
398.010
Hydration Free Energy
-10.610
Log(D) at pH=7.4
2.050
Log(P)
2.48
Log S
-3.9
Log(Vapor Pressure)
-6.82
Melting Point
213.97
pKa Acid
5.07
pKa Basic
4.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9623
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9360
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9347
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9253
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9231
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9198
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9150
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8969
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8935
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8899
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8884
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8825
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8776
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8762
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8743
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8733
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8644
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8591
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8550
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8533
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8518
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8504
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8483
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 3 0.8410
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8272
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8245
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8226
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8155
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8100
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8050
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8048
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8037
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8010
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7978
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7966
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7955
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7942
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7918
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 3 0.7886
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7865
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7834
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7803
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7780
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7756
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7740
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7705
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7686
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7685
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7677
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7658
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7654
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7653
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.7647
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7617
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7610
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7602
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7598
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7589
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7546
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7530
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7521
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7517
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 3 0.7515
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7511
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7490
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7487
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7473
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7465
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7465
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7431
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7416
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7412
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7411
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7408
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7379
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7370
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7369
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.7365
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7360
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7355
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7351
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7345
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7340
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7328
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7326
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7307
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7303
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7296
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7293
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7291
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7289
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7287
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7281
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7273
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7262
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7256
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7241
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7240
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 3 0.7236
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7214
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7212
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7202
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7191
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 3 0.7180
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7163
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7156
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7154
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7151
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7144
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7107
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7101
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7085
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7072
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7071
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7065
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7056
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7049
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7041
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7018
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7014
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7002

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