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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridone Alkaloid
Canonical Smiles COc1cc(O)cc2c1c(=O)c1c(n2C)cccc1
InChI InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(17)8-13(14)19-2/h3-8,17H,1-2H3
InChIKey UFEDIXBJQROJES-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
2 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]
  • Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]
Pubchem: 16220278
Nmrshiftdb2: 20249230

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)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.090
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
63.22
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
1.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.320
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.120
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
4.290
Rat (Acute)
2.060
Rat (Chronic Oral)
2.190
Fathead Minnow
4.750
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
402.890
Hydration Free Energy
-10.850
Log(D) at pH=7.4
1.100
Log(P)
2.36
Log S
-3.77
Log(Vapor Pressure)
-6.84
Melting Point
237.32
pKa Acid
5.69
pKa Basic
4.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9851
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9404
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9392
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9349
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9222
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9037
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9015
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8968
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8945
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8939
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8899
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8882
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8863
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8786
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8750
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8709
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8708
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8683
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8567
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8546
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8546
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8319
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8314
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8238
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8233
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8137
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8097
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8038
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7970
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7968
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7962
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7961
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7900
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7882
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7878
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7834
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7818
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7811
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7805
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7739
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7738
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7702
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7701
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7676
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7669
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7653
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7647
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7637
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7633
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7613
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7555
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7544
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7544
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7537
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7536
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7528
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7505
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7487
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7475
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7472
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7452
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7450
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7446
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7445
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7443
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7435
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7416
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7414
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7405
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7401
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.7386
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7380
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7380
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7377
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7375
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7357
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7353
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7351
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7349
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7309
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7300
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7288
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7283
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7280
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7250
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7232
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7230
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7229
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7215
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7215
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7200
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7195
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7191
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7188
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7187
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7167
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7153
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7152
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7151
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7148
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7134
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7128
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7117
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7090
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 2 0.7085
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7055
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7053
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7048
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7047
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7025
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7020
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7017
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7014
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7011
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7010
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7002
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7002

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