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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Quinolinone Alkaloid
Canonical Smiles CCCc1c([nH]c2c(c1=O)c(OC)ccc2OC)c1ccc(c(c1)OC)OC
InChI InChI=1S/C22H25NO5/c1-6-7-14-20(13-8-9-15(25-2)18(12-13)28-5)23-21-17(27-4)11-10-16(26-3)19(21)22(14)24/h8-12H,6-7H2,1-5H3,(H,23,24)
InChIKey OSTCLUSJTWXHEU-UHFFFAOYSA-N
Formula C22H25NO5
HBA 5
HBD 1
MW 383.44
Rotatable Bonds 7
TPSA 69.78
LogP 4.18
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 383.17
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: 24766569
Nmrshiftdb2: 70071980

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 383.44 g/mol

Structure

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

Level: 0

Mol. Weight: 383.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 383.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
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)
1.3
Plasma Protein Binding
75.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-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
6.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.19
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.2
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
-8.3
Rat (Acute)
2.43
Rat (Chronic Oral)
2.01
Fathead Minnow
5.08
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
470.15
Hydration Free Energy
-7.31
Log(D) at pH=7.4
2.97
Log(P)
4.04
Log S
-4.79
Log(Vapor Pressure)
-7.67
Melting Point
179.95
pKa Acid
9.06
pKa Basic
6.76
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 0.9633
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9633
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9572
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9572
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9342
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9342
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9263
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9263
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9192
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9192
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9077
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9077
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9004
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9004
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8951
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8951
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.8826
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.8826
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8815
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8815
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.8708
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.8708
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8704
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8704
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8691
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8691
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8620
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8620
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8608
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8608
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8567
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.8567
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8525
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8525
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8372
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8372
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8369
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8369
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8349
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8349
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8204
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8204
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8190
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8190
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8171
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8171
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8156
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8156
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8052
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8002
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8002
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7974
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7974
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7901
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7901
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7894
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7894
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7889
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7889
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7877
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7877
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7861
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7861
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7833
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7833
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7815
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7815
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7694
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7694
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7693
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7693
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7644
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7644
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7603
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7603
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7598
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7598
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7578
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7578
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7568
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7568
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7533
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7533
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7527
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7527
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7510
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7510
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7498
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7498
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7496
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7496
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7482
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7482
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7466
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7466
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7463
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7463
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7440
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7440
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7432
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7432
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7415
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7415
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7389
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7389
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7341
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7341
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7332
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7332
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7317
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7317
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7312
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7312
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7308
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7308
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7306
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7306
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7301
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7301
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7294
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7294
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7285
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7285
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7284
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7284
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7265
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7265
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7230
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7230
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7229
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7229
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7196
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7196
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7182
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7182
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7182
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7182
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7179
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7179
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7168
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7168
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 3 0.7143
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 3 0.7143
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7110
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7110
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7103
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7103
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7099
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7099
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7078
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7078
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7071
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7071
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7061
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7061
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7046
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7046
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7028
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7028
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7025
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7025
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7005
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7005
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7003
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7003
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7001
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7001

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