4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide - Compound Card

4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

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4-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyridine Alkaloid
Canonical Smiles COc1ccn(c(=O)c1C(=O)N)C
InChI InChI=1S/C8H10N2O3/c1-10-4-3-5(13-2)6(7(9)11)8(10)12/h3-4H,1-2H3,(H2,9,11)
InChIKey OFTNSOWAEPBVCF-UHFFFAOYSA-N
Formula C8H10N2O3
HBA 4
HBD 1
MW 182.18
Rotatable Bonds 2
TPSA 74.32
LogP -0.51
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 182.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ricinus communis Euphorbiaceae Plantae 3988

Showing of synonyms

  • El-Naggar M.H, Elgaml A, et al. (2019). Antimicrobial and antiquorum-sensing activity of Ricinus communis extracts and ricinine derivatives. Natural product research, 2019, 33(11), 1556-1562. [View] [PubMed]
Pubchem: 167313249

No compound-protein relationship available.

Structure

SMILES: O=c1cccc[nH]1

Level: 0

Mol. Weight: 182.18 g/mol

Antimicrobial
Antiquorum-sensing

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.240
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.370
Plasma Protein Binding
5.34
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.920
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.760
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.950
Micronucleos
Toxic
NR-AhR
Safe
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
1.900
Rat (Acute)
1.790
Rat (Chronic Oral)
1.670
Fathead Minnow
3.490
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
330.130
Hydration Free Energy
-15.110
Log(D) at pH=7.4
-0.650
Log(P)
-0.87
Log S
-0.69
Log(Vapor Pressure)
-5.75
Melting Point
212.55
pKa Acid
8.01
pKa Basic
6.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 3 0.9776
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.9557
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9366
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9345
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9249
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.9045
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9010
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9009
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9006
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8971
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8959
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8916
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8831
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8662
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8566
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8544
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8502
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8497
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8469
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8462
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8460
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8441
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8419
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 3 0.8409
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8399
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8367
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8333
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8319
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8289
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8276
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.8275
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8223
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.8201
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8183
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 3 0.8122
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8119
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8029
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7994
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7981
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7967
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7910
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7903
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7903
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7892
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7848
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7829
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7816
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7791
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7774
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7742
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7741
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7734
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7725
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7692
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7643
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7633
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7597
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7575
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7573
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7572
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7558
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7494
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7474
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7445
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7443
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7412
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7403
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7396
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7389
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7386
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7373
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7361
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7357
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7348
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7342
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7322
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7309
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7286
Lactoperoxidase A5JUY8 PERL_BUBBU Bubalus bubalis 3 0.7285
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7280
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7275
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7272
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7245
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7241
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7241
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7235
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7214
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7192
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7145
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7127
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7118
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7117
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7112
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7103
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7100
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7094
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 3 0.7080
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7072
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7062
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7057
Cytochrome P450 monooxygenase PikC O87605 PIKC_STRVZ Streptomyces venezuelae 2 0.7049
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7031
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7027
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7018
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7013
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7008

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