Coumarin - Compound Card

Coumarin

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Coumarin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles O=c1ccc2c(o1)cccc2
InChI InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
InChIKey ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Formula C9H6O2
HBA 2
HBD 0
MW 146.15
Rotatable Bonds 0
TPSA 30.21
LogP 1.79
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 146.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia reptans Asteraceae Plantae 72350
2 Coriandrum sativum Apiaceae Plantae 4047

Showing of synonyms

  • Msaada K, Ben Jemia M, et al. (2014). Antioxidant activity of methanolic extracts from three coriander (Coriandrum sativum L.) fruit varieties. Arabian Journal of Chemistry,2014, in press. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones and acetylenes from Artemisia reptans.. Phytochemistry,1994,37(4),1055-1099. [View]
Pubchem: 323
Kegg Ligand: C05851
Chebi: 28794
Nmrshiftdb2: 10008786
Metabolights: MTBLC28794
Chembl: CHEMBL6466
Drugbank: DB04665
Pdb Ligand: COU
Bindingdb: 12342
Selleck: coumarin
CPRiL: 4038
Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 146.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.3
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
54.78
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.030
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.850
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.480
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.050
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
3.380
Rat (Acute)
2.290
Rat (Chronic Oral)
1.760
Fathead Minnow
3.940
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
283.600
Hydration Free Energy
-6.880
Log(D) at pH=7.4
1.620
Log(P)
1.56
Log S
-1.85
Log(Vapor Pressure)
-2.22
Melting Point
95.48
pKa Acid
4.5
pKa Basic
1.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9947
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9947
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9493
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9493
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.9410
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.9410
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9243
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9243
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9236
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9081
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9081
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8985
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8985
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8602
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8602
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8585
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8585
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8561
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8561
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8423
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8423
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8291
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8181
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.8049
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.8049
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7950
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7950
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7943
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7943
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7939
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7939
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7918
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7918
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7913
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7913
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7894
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7894
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7882
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7882
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7792
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7792
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7779
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7779
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7769
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7769
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7740
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7740
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7736
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7736
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7720
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7720
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7688
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7688
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7677
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7677
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7674
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7674
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7674
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7674
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7671
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7671
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7659
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7659
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7617
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7617
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7614
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7614
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7594
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7594
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7552
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7552
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7550
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7550
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7547
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7547
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7544
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7544
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7540
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7540
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7532
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 2 0.7532
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7522
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7522
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7520
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7520
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7518
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7518
Envelope glycoprotein gp160 C6G099 C6G099_9HIV1 Human immunodeficiency virus 1 2 0.7516
Envelope glycoprotein gp160 C6G099 C6G099_9HIV1 Human immunodeficiency virus 1 2 0.7516
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7506
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7506
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7505
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7505
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7495
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7495
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7478
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7478
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7478
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7478
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7474
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7474
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7459
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7459
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7458
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7458
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7458
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7458
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7453
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7453
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7452
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7452
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7452
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7452
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7448
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7448
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7447
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7447
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7446
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7446
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7411
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7411
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7406
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7406
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7403
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7403
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7393
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7393
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7384
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7384
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 2 0.7378
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 2 0.7378
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7373
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7373
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7364
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7364
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7363
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7363
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7362
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7362
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7360
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7360
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7352
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7352
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7340
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7340
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7338
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7338
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7322
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7322
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7321
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7321
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7317
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7317
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7316
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7316
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7316
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7316
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7310
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7310
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7301
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7301
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7299
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7299
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7292
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7292
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7290
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7290
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7288
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7288
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7287
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7287
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7286
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7286
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7285
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7285
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7285
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7285
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7273
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7273
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7270
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7270
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7270
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7270
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7268
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7268
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7258
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7258
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7241
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7241
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7239
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7239
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7238
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7238
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7234
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7234
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7223
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7223
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7212
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7212
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7211
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7211
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7210
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7210
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7209
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7209
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7203
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7203
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7202
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7202
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 2 0.7197
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7197
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 2 0.7197
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7197
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7193
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7193
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7188
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7188
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7180
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7180
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7178
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7178
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7173
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7173
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7172
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7172
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7169
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7169
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7167
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7167
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7166
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7166
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7152
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7152
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7149
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7149
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic O96693 DXR_PLAFX Plasmodium falciparum 2 0.7141
1-deoxy-D-xylulose 5-phosphate reductoisomerase, apicoplastic O96693 DXR_PLAFX Plasmodium falciparum 2 0.7141
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7132
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7132
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7131
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7131
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7124
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7124
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7123
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7123
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7121
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7121
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7115
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7115
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7094
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7094
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7093
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7093
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7093
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7093
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7089
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7089
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7086
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7086
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7080
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7080
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7079
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7079
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7064
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7064
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7064
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7064
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7053
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7053
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7051
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7051
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 2 0.7048
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 2 0.7048
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7038
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7038
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7038
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7038
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7034
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7034
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7031
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7031
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7027
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7026
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7026
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7013
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7013
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 2 0.7009
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 2 0.7009

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