2'-hydroxy-5'-(7''-methoxycoumarin-6''-yl)-4'-methoxyphenylpropanoic acid - Compound Card

2'-hydroxy-5'-(7''-methoxycoumarin-6''-yl)-4'-methoxyphenylpropanoic acid

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2'-hydroxy-5'-(7''-methoxycoumarin-6''-yl)-4'-methoxyphenylpropanoic acid

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Coumarin Derivative
Canonical Smiles COc1cc(O)c(cc1c1cc2ccc(=O)oc2cc1OC)CCC(=O)O
InChI InChI=1S/C20H18O7/c1-25-17-9-15(21)11(3-5-19(22)23)7-13(17)14-8-12-4-6-20(24)27-16(12)10-18(14)26-2/h4,6-10,21H,3,5H2,1-2H3,(H,22,23)
InChIKey CLTULMKJHXAQIM-UHFFFAOYSA-N
Formula C20H18O7
HBA 6
HBD 2
MW 370.36
Rotatable Bonds 6
TPSA 106.2
LogP 3.2
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 370.11
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]

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)ccc(c2)-c3ccccc3

Level: 1

Mol. Weight: 370.36 g/mol

Structure

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

Level: 0

Mol. Weight: 370.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 370.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.010
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
Non-Penetrable
Fraction Unbound (Human)
1.900
Plasma Protein Binding
71.95
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
8.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.080
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.300
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.850
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
-0.970
Rat (Acute)
2.290
Rat (Chronic Oral)
2.450
Fathead Minnow
4.350
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
502.720
Hydration Free Energy
-6.440
Log(D) at pH=7.4
0.440
Log(P)
2.98
Log S
-4.09
Log(Vapor Pressure)
-9.46
Melting Point
197.55
pKa Acid
6.57
pKa Basic
5.52
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 0.9731
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9684
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.9656
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9596
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9534
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9445
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9427
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9386
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9376
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9373
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9314
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9313
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9294
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9288
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.9256
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9187
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9142
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9142
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9117
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.9088
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9082
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9052
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.9039
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9037
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9018
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9009
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8999
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8983
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.8982
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8961
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8936
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8934
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8933
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8919
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8917
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8905
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8895
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8893
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.8862
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8820
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8809
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8785
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8750
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8730
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8708
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8703
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8690
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8686
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8682
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8676
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.8675
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 5 0.8671
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8671
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8667
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8658
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8653
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8640
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8639
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8631
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8621
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8602
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8591
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8591
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.8570
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8565
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.8543
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8539
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8504
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8503
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 3 0.8484
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.8478
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8468
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8467
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8421
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.8408
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8404
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8393
Neutrophil collagenase P22894 MMP8_HUMAN Homo sapiens 3 0.8386
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8380
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8354
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8350
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8313
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8307
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8295
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8282
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8277
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8266
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8260
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8253
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8249
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8248
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8238
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8235
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8196
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8193
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8190
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.8182
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.8181
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8167
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8160
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8146
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8144
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8141
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8129
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 3 0.8125
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8117
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8105
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8101
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8086
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8076
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8050
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8050
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8035
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8032
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8031
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8023
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8013
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.8010
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 5 0.8007
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8005
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8000
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8000
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7997
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7990
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7987
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7979
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 5 0.7976
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7966
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7957
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7936
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7934
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7929
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.7922
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7912
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7894
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7880
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7870
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7865
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7857
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7855
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7847
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 5 0.7845
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7834
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7833
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7830
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7829
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7824
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7810
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7807
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7804
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7797
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7796
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7783
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7779
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7773
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7747
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7687
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7683
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 3 0.7683
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7673
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7673
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7658
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7658
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7646
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7645
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7645
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7638
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7634
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7634
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7626
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 5 0.7621
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7621
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7616
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7614
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7604
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7604
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7604
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7601
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7593
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7587
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7583
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7575
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7561
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7555
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7554
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7553
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7547
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7542
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7533
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7530
Flagellum-specific ATP synthase P26465 FLII_SALTY Salmonella typhimurium 2 0.7529
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7526
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7526
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7525
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7525
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7519
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7518
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7517
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7511
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 4 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7508
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7502
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7498
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7498
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7494
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7492
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7488
Mitogen-activated protein kinase kinase kinase 21 Q5TCX8 M3K21_HUMAN Homo sapiens 3 0.7487
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7484
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7484
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7483
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7476
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7474
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7470
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 3 0.7470
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7464
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7463
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7460
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7455
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7452
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7448
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7437
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7430
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7420
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7420
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7419
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7418
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7414
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7407
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7404
Nitrogen regulatory protein P-II P70731 P70731_AZOBR Azospirillum brasilense 3 0.7401
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7399
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7390
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7389
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7383
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7382
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7381
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.7375
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7370
Nucleoside diphosphate kinase O58429 NDK_PYRHO Pyrococcus horikoshii 3 0.7367
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7365
Sulfotransferase 1E1 P49891 ST1E1_MOUSE Mus musculus 4 0.7358
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7357
Thymidylate kinase Q9HZN8 KTHY_PSEAE Pseudomonas aeruginosa 4 0.7342
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7342
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7335
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7329
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7328
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7323
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7322
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7322
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7321
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7316
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7315
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7310
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7301
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 3 0.7293
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7292
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7284
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7279
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7274
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7274
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7272
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7270
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7266
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7265
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7253
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7248
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7246
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7246
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7242
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7234
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7207
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7204
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7197
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7190
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7190
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7188
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 3 0.7183
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7176
Nucleoside diphosphate kinase, cytosolic P22887 NDKC_DICDI Dictyostelium discoideum 3 0.7168
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7157
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7153
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7152
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7152
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7145
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7144
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7144
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7142
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7139
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7136
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 4 0.7133
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 4 0.7133
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7130
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7124
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7123
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7123
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7121
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7118
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7117
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7112
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7103
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7092
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.7091
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7091
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7070
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7068
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7061
Type 4 fimbrial biogenesis protein PilM G3XD28 G3XD28_PSEAE Pseudomonas aeruginosa 3 0.7056
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7055
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7050
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7050
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7047
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7045
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7043
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7041
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7038
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.7038
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.7037
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7033
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7033
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7023
Histone H3 P61830 H3_YEAST Saccharomyces cerevisiae 2 0.7022
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7018
Metabotropic glutamate receptor 7 Q14831 GRM7_HUMAN Homo sapiens 3 0.7018
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7018
mRNA-capping enzyme subunit alpha P78587 MCE1_CANAX Candida albicans 3 0.7012
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7007
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7002

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