7-methoxy- 6,7'-dicoumarinyl ether - Compound Card

7-methoxy- 6,7'-dicoumarinyl ether

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7-methoxy- 6,7'-dicoumarinyl ether

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Derivative
Canonical Smiles COc1cc2oc(=O)ccc2cc1Oc1ccc2c(c1)oc(=O)cc2
InChI InChI=1S/C19H12O6/c1-22-16-10-15-12(4-7-19(21)25-15)8-17(16)23-13-5-2-11-3-6-18(20)24-14(11)9-13/h2-10H,1H3
InChIKey GJFYDYXKONYNND-UHFFFAOYSA-N
Formula C19H12O6
HBA 6
HBD 0
MW 336.3
Rotatable Bonds 3
TPSA 78.88
LogP 3.7
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.05
Exact Mass 336.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum riparium Guttiferae Plantae 269018

Showing of synonyms

  • Tanemossu SA, Franke K, et al. (2014). Rare biscoumarin derivatives and flavonoids from Hypericum riparium.. Phytochemistry,2014, 105, 171-177. [View] [PubMed]
Pubchem: 162885890

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)ccc(c2)Oc(cc3)cc(c34)oc(=O)cc4

Level: 1

Mol. Weight: 336.3 g/mol

Structure

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

Level: 0

Mol. Weight: 336.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.530
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.770
Plasma Protein Binding
91.59
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.620
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.490
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.650
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.560
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
1.390
Rat (Acute)
2.220
Rat (Chronic Oral)
1.130
Fathead Minnow
5.420
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
492.300
Hydration Free Energy
-8.670
Log(D) at pH=7.4
2.620
Log(P)
2.65
Log S
-5.56
Log(Vapor Pressure)
-8.55
Melting Point
255.52
pKa Acid
7.03
pKa Basic
2.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9705
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9621
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9402
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9392
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.9390
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9385
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9373
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9362
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.9353
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9328
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.9306
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9300
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9210
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9151
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9150
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9150
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.9138
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9106
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9082
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9046
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9022
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9008
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9003
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8897
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8889
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8887
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8858
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8857
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8856
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.8854
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8844
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8819
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8800
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8777
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8776
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8746
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8713
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8707
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8676
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8654
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8569
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8564
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8514
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8504
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8487
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8480
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8447
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8435
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8392
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8385
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8357
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8333
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8331
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8329
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.8309
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8298
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8292
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8265
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8240
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8240
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8227
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8207
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8173
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8135
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8131
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.8122
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8114
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8082
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8077
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8058
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8057
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.8045
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8013
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8005
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8005
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7997
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7977
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7973
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7971
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7949
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7948
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7945
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7945
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7943
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7941
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7934
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7921
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7915
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7906
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7898
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7886
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7883
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7868
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7865
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7854
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7851
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7849
CRP-like cAMP-activated global transcriptional regulator P9WMH3 CRPL_MYCTU Mycobacterium tuberculosis 3 0.7840
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7839
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7827
Mu-type opioid receptor P42866 OPRM_MOUSE Mus musculus 3 0.7826
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7816
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7784
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7783
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7769
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7769
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7767
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7764
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7755
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7752
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7746
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7745
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7728
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7723
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7721
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7718
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7717
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7714
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7707
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7699
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7689
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7686
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7683
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7682
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7679
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7674
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7673
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7661
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7655
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7652
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7641
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7628
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7624
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7619
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.7618
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7612
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7606
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7599
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7598
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7595
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7593
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7588
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7569
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7566
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7563
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7563
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7557
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7545
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7543
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7540
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7539
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7533
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7533
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7529
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7526
Casein kinase I homolog 1 P40233 CKI1_SCHPO Schizosaccharomyces pombe 4 0.7520
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7519
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7518
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7517
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7511
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7505
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7505
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7504
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7504
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7494
Cyclin-dependent kinase 2 homolog Q5CRJ8 Q5CRJ8_CRYPI Cryptosporidium parvum 4 0.7493
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7493
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 2 0.7487
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7481
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7474
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7470
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7465
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7465
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7463
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7461
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7457
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7451
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7450
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7446
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7442
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7438
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7434
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7433
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7428
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7428
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7427
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7421
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7418
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7412
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7410
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7409
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7402
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7398
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7390
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7390
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7389
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7383
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7376
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7367
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7354
Endoplasmic reticulum aminopeptidase 2 Q6P179 ERAP2_HUMAN Homo sapiens 2 0.7354
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7352
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7340
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7335
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7333
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 3 0.7331
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7330
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7323
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7318
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7317
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7314
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7309
Genome polyprotein O93077 O93077_9HEPC Hepacivirus hominis 3 0.7306
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7305
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7305
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7297
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7296
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7291
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7290
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7290
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7280
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7277
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7270
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7267
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7267
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7265
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7264
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7264
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 2 0.7263
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7262
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7255
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7249
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7243
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7242
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7242
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7239
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7235
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 3 0.7234
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7233
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7223
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7218
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7215
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 2 0.7214
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7213
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7211
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7208
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7205
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7204
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7200
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7195
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7194
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7184
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7184
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7178
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7172
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7166
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7164
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7158
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7153
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7153
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7150
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7148
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7145
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7143
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7138
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7138
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7131
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7125
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7121
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7113
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7109
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 3 0.7104
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7103
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7095
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7092
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7090
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7088
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7086
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7084
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7083
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7075
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7073
Phosphoenolpyruvate carboxykinase [GTP] A5TYT6 PCKG_MYCTA Mycobacterium tuberculosis 3 0.7073
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 2 0.7072
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7070
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7065
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 4 0.7063
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7062
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7061
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7059
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7059
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7057
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7054
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7053
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7053
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7050
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7047
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7044
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7036
Dual specificity tyrosine-phosphorylation-regulated kinase 1A Q13627 DYR1A_HUMAN Homo sapiens 4 0.7035
Ephrin type-A receptor 3 P29320 EPHA3_HUMAN Homo sapiens 3 0.7034
ADP-dependent (S)-NAD(P)H-hydrate dehydratase P94368 NNRD_BACSU Bacillus subtilis 3 0.7034
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7028
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7026
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7026
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7025
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7021
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7019
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7018
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7016
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7007
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 3 0.7001
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7001

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