1,3-dihydroxy-2-methoxy-10-methyl-9-acridone - Compound Card

1,3-dihydroxy-2-methoxy-10-methyl-9-acridone

Select a section from the left sidebar

1,3-dihydroxy-2-methoxy-10-methyl-9-acridone

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridine Alkaloid
Canonical Smiles COc1c(O)cc2c(c1O)c(=O)c1c(n2C)cccc1
InChI InChI=1S/C15H13NO4/c1-16-9-6-4-3-5-8(9)13(18)12-10(16)7-11(17)15(20-2)14(12)19/h3-7,17,19H,1-2H3
InChIKey MEIZZDBRRJMWCJ-UHFFFAOYSA-N
Formula C15H13NO4
HBA 5
HBD 2
MW 271.27
Rotatable Bonds 1
TPSA 71.69
LogP 2.11
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 271.08
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: 91739029
Nmrshiftdb2: 60028693

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 271.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.310
Plasma Protein Binding
65.91
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.750
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.380
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
3.900
Rat (Acute)
2.230
Rat (Chronic Oral)
2.820
Fathead Minnow
4.570
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
401.420
Hydration Free Energy
-10.110
Log(D) at pH=7.4
1.700
Log(P)
2.23
Log S
-3.92
Log(Vapor Pressure)
-7.06
Melting Point
244.68
pKa Acid
6.47
pKa Basic
5.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9564
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9367
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9285
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9225
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9206
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9192
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9097
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9085
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9082
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9018
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 4 0.8976
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8963
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8913
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8788
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8747
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.8696
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8629
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8629
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8622
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8592
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.8586
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8569
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8564
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8543
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8538
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8531
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8504
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8481
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8381
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8314
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8253
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8240
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8214
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8212
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8186
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8165
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8154
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8129
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8119
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8095
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8078
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8066
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8063
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8039
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8014
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8007
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7998
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7995
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 3 0.7976
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7976
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7970
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7917
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7911
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7901
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7895
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7890
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7875
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7823
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7787
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7779
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7767
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7766
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7755
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7725
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7716
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7709
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7699
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7698
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7671
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7666
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7653
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7640
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7640
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7639
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7638
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7624
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7618
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7616
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7616
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7610
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7597
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7565
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7557
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7547
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7531
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7520
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7503
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7481
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7475
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7460
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7458
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7418
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7395
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7382
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7359
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7355
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7348
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7342
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7339
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7333
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7324
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7299
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7278
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7276
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7259
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7257
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7242
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7239
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7221
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7215
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7213
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7208
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7188
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7182
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7177
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7169
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7143
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7134
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7131
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7127
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7125
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7124
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7119
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7111
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 4 0.7099
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7094
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7065
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7061
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7061
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7056
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7055
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7035
Tyrosine-protein phosphatase non-receptor type 1 P18031 PTN1_HUMAN Homo sapiens 4 0.7033
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7029
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7028
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7020
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7020
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7019
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7014
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7012
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7010
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7004

Download SDF