5,8-dimethoxy-2-(3'-methoxyphenyl)-3-propyl-1H-quinolin-4- one - Compound Card

5,8-dimethoxy-2-(3'-methoxyphenyl)-3-propyl-1H-quinolin-4- one

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5,8-dimethoxy-2-(3'-methoxyphenyl)-3-propyl-1H-quinolin-4- one

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinolinone Alkaloid
Canonical Smiles CCCc1c([nH]c2c(c1=O)c(OC)ccc2OC)c1cccc(c1)OC
InChI InChI=1S/C21H23NO4/c1-5-7-15-19(13-8-6-9-14(12-13)24-2)22-20-17(26-4)11-10-16(25-3)18(20)21(15)23/h6,8-12H,5,7H2,1-4H3,(H,22,23)
InChIKey BAMLXOXNWWAWAS-UHFFFAOYSA-N
Formula C21H23NO4
HBA 4
HBD 1
MW 353.42
Rotatable Bonds 6
TPSA 60.55
LogP 4.17
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 353.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Casimiroa edulis Rutaceae Plantae 68535

Showing of synonyms

  • Awaad AS, Maitland DJ, et al. (2007). New alkaloids from Casimiroa edulis fruits and their pharmacological activity. Chemistry of Natural Compounds,2007,43(5),576-580. [View]
Pubchem: 24766570
Nmrshiftdb2: 70071983

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]c(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 221.26 g/mol

Structure

SMILES: c1cccc(c12)[nH]ccc2=O

Level: 0

Mol. Weight: 145.16 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.32
Plasma Protein Binding
75.48
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.9
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
-0.59
Rat (Acute)
2.21
Rat (Chronic Oral)
2.0
Fathead Minnow
4.99
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
460.03
Hydration Free Energy
-8.93
Log(D) at pH=7.4
3.27
Log(P)
4.54
Log S
-5.59
Log(Vapor Pressure)
-7.62
Melting Point
164.75
pKa Acid
8.94
pKa Basic
7.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9641
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9641
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9633
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9633
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9378
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9378
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9246
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9246
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9023
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9023
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9007
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.8921
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.8921
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8802
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8802
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8798
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8798
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8672
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8672
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8648
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8648
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8645
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8645
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8626
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8626
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8626
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8626
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8558
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8558
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8529
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8529
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8504
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8504
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8416
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8416
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8410
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8410
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8374
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8374
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8321
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8321
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8231
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8231
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8203
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8203
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8068
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8068
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7922
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7922
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7909
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7909
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7878
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7878
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7834
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7834
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7653
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7653
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7637
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7637
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7630
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7630
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7596
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7596
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7576
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7576
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7547
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7547
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7541
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7541
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7497
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7497
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7496
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7496
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7470
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7466
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7466
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7459
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7459
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7435
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7435
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7426
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7426
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7425
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7425
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7398
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7398
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7365
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7365
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7355
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7355
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7354
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7354
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7347
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7347
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7346
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7346
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7345
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7345
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7323
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7323
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7315
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7315
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7304
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7304
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7302
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7302
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7299
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7299
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7281
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7281
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7277
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7277
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7276
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7276
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7248
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7248
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7242
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7242
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7228
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7225
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7225
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 3 0.7220
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 3 0.7220
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7195
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7195
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7191
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7191
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7181
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7181
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7171
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7171
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7160
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7160
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7149
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7149
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7132
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7132
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7129
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7129
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7096
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7096
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7093
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7093
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7077
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7077
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7072
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7072
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7065
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7045
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7045
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7023
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7023
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7009
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7009
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7009
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7009

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