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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridine Alkaloid
Canonical Smiles COc1cc2c(c(c1O)O)c(=O)c1c(n2C)cccc1
InChI InChI=1S/C15H13NO4/c1-16-9-6-4-3-5-8(9)13(17)12-10(16)7-11(20-2)14(18)15(12)19/h3-7,18-19H,1-2H3
InChIKey NUNVWSSVDPNHPV-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: 132277135
Nmrshiftdb2: 60028694

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)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.450
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.270
Plasma Protein Binding
65.63
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
1.960
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.940
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.370
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
4.170
Rat (Acute)
2.240
Rat (Chronic Oral)
2.730
Fathead Minnow
4.670
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
407.840
Hydration Free Energy
-10.380
Log(D) at pH=7.4
1.280
Log(P)
1.37
Log S
-3.77
Log(Vapor Pressure)
-7.29
Melting Point
226.16
pKa Acid
5.46
pKa Basic
5.77
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 0.9573
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9407
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9271
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9212
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9079
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9017
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8993
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8956
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8764
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8738
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8668
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8630
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8602
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.8589
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8550
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8535
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8489
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8451
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8423
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8351
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8346
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8332
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8282
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8210
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.8144
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8134
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8118
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8110
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8095
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8054
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8048
Uricase Q00511 URIC_ASPFL Aspergillus flavus 4 0.8043
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8031
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8004
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7990
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7984
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7983
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7971
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7955
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7954
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7949
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7941
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7931
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7922
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7892
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7881
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7870
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7854
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7811
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7803
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7790
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7782
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7781
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7774
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7742
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7719
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7712
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7674
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7652
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7647
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7626
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7620
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7589
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7588
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7564
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7560
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7543
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7535
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7520
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 3 0.7518
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7494
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7485
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7472
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7463
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.7451
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7441
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7432
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 3 0.7429
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7420
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7416
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7414
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7414
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7409
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 5 0.7400
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7391
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7390
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7381
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7378
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7375
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7366
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7359
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7350
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7347
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7342
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7335
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7332
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7329
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7312
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7306
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.7292
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7288
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7282
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7275
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7273
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7259
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7255
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7246
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7244
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7232
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7224
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7223
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7221
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7217
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7213
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7203
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7198
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7194
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7188
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7182
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7180
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.7179
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7159
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7150
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7150
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7145
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7133
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7120
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7118
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7107
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7105
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7105
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7104
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7090
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7058
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7054
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7051
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7046
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7042
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7034
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7022
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7012
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7001

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