3-amino-5-methyl-1-(phenylsulfonyl)-1H-pyrazolo[4,3-c]pyridin-4(5H)-one - Compound Card

3-amino-5-methyl-1-(phenylsulfonyl)-1H-pyrazolo[4,3-c]pyridin-4(5H)-one

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3-amino-5-methyl-1-(phenylsulfonyl)-1H-pyrazolo[4,3-c]pyridin-4(5H)-one

Structure
Zoomed Structure
  • Family: Euphorbiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyridine Alkaloid
Canonical Smiles Nc1nn(c2c1c(=O)n(C)cc2)S(=O)(=O)c1ccccc1
InChI InChI=1S/C13H12N4O3S/c1-16-8-7-10-11(13(16)18)12(14)15-17(10)21(19,20)9-5-3-2-4-6-9/h2-8H,1H3,(H2,14,15)
InChIKey SZHSGUDHQBVFLW-UHFFFAOYSA-N
Formula C13H12N4O3S
HBA 7
HBD 1
MW 304.33
Rotatable Bonds 2
TPSA 99.98
LogP 0.55
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 304.06
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]

No compound-protein relationship available.

Structure

SMILES: O=c1[nH]ccc(c12)n(nc2)S(=O)(=O)c3ccccc3

Level: 1

Mol. Weight: 275.29 g/mol

Structure

SMILES: c1n[nH]c(c12)cc[nH]c2=O

Level: 0

Mol. Weight: 135.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Antimicrobial
Antiquorum-sensing

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.390
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
61.36
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.050
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.270
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.820
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.170
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
2.590
Rat (Acute)
2.130
Rat (Chronic Oral)
1.240
Fathead Minnow
4.570
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
449.440
Hydration Free Energy
-14.820
Log(D) at pH=7.4
0.270
Log(P)
0.82
Log S
-3.48
Log(Vapor Pressure)
-9.03
Melting Point
277.16
pKa Acid
4.98
pKa Basic
3.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9548
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9408
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9184
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9146
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9127
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9090
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.9028
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8874
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8742
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8611
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8611
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8573
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.8538
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8533
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.8528
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8466
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8370
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8305
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8289
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8270
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8249
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8227
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.8209
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8186
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.8179
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8130
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8118
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8101
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8083
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.8019
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.8005
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7987
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7982
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7970
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7959
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7943
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7939
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7930
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7922
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7914
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7911
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7888
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7866
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7852
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7835
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7830
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7827
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7821
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7819
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7811
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7801
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7800
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7780
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7778
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.7762
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7748
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7741
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7737
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7730
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7716
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7712
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7709
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7705
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7685
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7659
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7634
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7622
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7618
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7610
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7578
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7570
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 4 0.7568
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7550
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7535
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7510
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7490
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7471
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7460
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7430
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7426
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7425
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7425
AGAP001556-PA Q7PXT9 Q7PXT9_ANOGA Anopheles gambiae 3 0.7401
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7399
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7395
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7391
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7385
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7378
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7378
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7374
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7365
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7358
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7346
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7343
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7339
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7333
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7329
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7324
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7322
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7322
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7322
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 4 0.7318
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7316
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7312
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7309
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7295
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7291
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7280
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7277
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7274
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7268
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7259
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7259
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7239
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7235
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7233
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7227
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7223
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7207
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7204
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 2 0.7203
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7195
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7189
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7167
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7164
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7161
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7151
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7150
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7145
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7136
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7132
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7130
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7129
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7127
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7122
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7114
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7096
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7096
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7095
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 5 0.7093
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7089
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7088
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7083
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7078
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7077
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7058
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7048
Cytochrome P450 monooxygenase PikC O87605 PIKC_STRVZ Streptomyces venezuelae 2 0.7043
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7035
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7027
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7022

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