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5,7-dihydroxy-3-(4'-methoxybenzyl)-4-chromanone
- Family: Plantae - Hyacinthaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Homoisoflavonoid
| Canonical Smiles | COc1ccc(cc1)CC1COc2c(C1=O)c(O)cc(c2)O |
|---|---|
| InChI | InChI=1S/C17H16O5/c1-21-13-4-2-10(3-5-13)6-11-9-22-15-8-12(18)7-14(19)16(15)17(11)20/h2-5,7-8,11,18-19H,6,9H2,1H3 |
| InChIKey | IERGURVELWCYAW-UHFFFAOYSA-N |
| Formula | C17H16O5 |
| HBA | 5 |
| HBD | 2 |
| MW | 300.31 |
| Rotatable Bonds | 3 |
| TPSA | 75.99 |
| LogP | 2.54 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 300.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ledebouria graminifolia | Hyacinthaceae | Plantae | 2826844 |
Showing of synonyms
5,7-dihydroxy-3-(4'-methoxybenzyl)-4-chromanone
3,9-Dihydroeucomin
887375-68-0
5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-2,3-dihydrochromen-4-one
SCHEMBL6276129
CHEMBL4459503
MKB37568
(3R)-5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-2,3-dihydrochromen-4-one
DA-69899
NCGC00385930-01!5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-2,3-dihydrochromen-4-one
- Mutanyatta J, Matapa BG, et al. (2003). Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids. Phytochemistry, 2003, 62(5), 797–804. [View]
Pubchem:
11415348
Cas:
887375-68-0
Gnps:
CCMSLIB00000845498
Nmrshiftdb2:
70097476
Chembl:
CHEMBL4459503
No compound-protein relationship available.
SMILES: c1ccccc1CC(C2=O)COc(c23)cccc3
Level: 1
Mol. Weight: 300.31 g/mol
SMILES: c1cccc(c12)OCCC2=O
Level: 0
Mol. Weight: 300.31 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 300.31 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.56
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.690
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.22
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.150
- Plasma Protein Binding
- 57.44
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.680
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.860
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.330
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- 4.310
- Rat (Acute)
- 1.960
- Rat (Chronic Oral)
- 2.830
- Fathead Minnow
- 4.460
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 410.170
- Hydration Free Energy
- -9.850
- Log(D) at pH=7.4
- 2.900
- Log(P)
- 3.22
- Log S
- -5.52
- Log(Vapor Pressure)
- -7.57
- Melting Point
- 153.5
- pKa Acid
- 7.31
- pKa Basic
- 5.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9570 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.9412 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9392 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 3 | 0.9342 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9340 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9270 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.9090 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.9067 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.9065 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 4 | 0.9024 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8938 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8936 |
| Decaprenylphosphoryl-beta-D-ribose oxidase | I6X8C4 | I6X8C4_MYCTU | Mycobacterium tuberculosis | 3 | 0.8931 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.8887 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 3 | 0.8880 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8870 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8856 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8820 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.8776 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.8755 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8744 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.8723 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8719 |
| Cyclic dipeptide N-prenyltransferase | D1D8L6 | D1D8L6_ASPFM | Neosartorya fumigata | 3 | 0.8716 |
| IOMT 3 | Q06YR3 | Q06YR3_MEDTR | Medicago truncatula | 4 | 0.8672 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8664 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 4 | 0.8655 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8647 |
| UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase | Q8DNV6 | Q8DNV6_STRR6 | Streptococcus pneumoniae | 3 | 0.8629 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8627 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8619 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8617 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8609 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 4 | 0.8605 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.8597 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8596 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 4 | 0.8593 |
| Isoliquiritigenin 2'-O-methyltransferase | P93324 | CHOMT_MEDSA | Medicago sativa | 4 | 0.8582 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8526 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8521 |
| Calmodulin-domain protein kinase 1, putative | A3FQ16 | A3FQ16_CRYPI | Cryptosporidium parvum | 3 | 0.8520 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8510 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.8499 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8477 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8475 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8472 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.8467 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.8466 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8451 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8432 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8410 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8380 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8345 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 4 | 0.8337 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8333 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8323 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8310 |
| Pteridine reductase | O76290 | O76290_TRYBB | Trypanosoma brucei brucei | 3 | 0.8298 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.8291 |
| Dihydrofolate reductase | P22906 | DYR_CANAX | Candida albicans | 4 | 0.8257 |
| Heat shock protein HSP 90-beta | P08238 | HS90B_HUMAN | Homo sapiens | 3 | 0.8256 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 3 | 0.8249 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8231 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8196 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8192 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8187 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.8185 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.8165 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8158 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8133 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 4 | 0.8130 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8126 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.8108 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8103 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.8093 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.8087 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.8081 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 4 | 0.8076 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 3 | 0.8076 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.8069 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8069 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8059 |
| Matrilysin | P09237 | MMP7_HUMAN | Homo sapiens | 3 | 0.8043 |
| Calmodulin-like domain protein kinase isoenzyme gamma, related | F0V9W9 | F0V9W9_NEOCL | Neospora caninum | 3 | 0.8041 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.8031 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.8024 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8023 |
| Calmodulin-domain protein kinase 1, putative | A3FQ16 | A3FQ16_CRYPI | Cryptosporidium parvum | 4 | 0.8018 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8008 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7995 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7978 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 3 | 0.7964 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7950 |
| BMP-2-inducible protein kinase | Q9NSY1 | BMP2K_HUMAN | Homo sapiens | 3 | 0.7945 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 4 | 0.7944 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7921 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7913 |
| Chalcone--flavanone isomerase 1 | P28012 | CFI1_MEDSA | Medicago sativa | 3 | 0.7907 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7894 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7884 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7883 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7873 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7865 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7860 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7860 |
| Transthyretin | P02766 | TTHY_HUMAN | Homo sapiens | 4 | 0.7844 |
| Single-strand selective monofunctional uracil DNA glycosylase | Q9YGN6 | SMUG1_XENLA | Xenopus laevis | 4 | 0.7844 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 4 | 0.7833 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7813 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7809 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7806 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7803 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7801 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 5 | 0.7798 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7795 |
| Cyclin-G-associated kinase | O14976 | GAK_HUMAN | Homo sapiens | 4 | 0.7786 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7782 |
| C-1-tetrahydrofolate synthase, cytoplasmic | P11586 | C1TC_HUMAN | Homo sapiens | 4 | 0.7773 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 | O88703 | HCN2_MOUSE | Mus musculus | 3 | 0.7770 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 3 | 0.7763 |
| orotidine-5'-phosphate decarboxylase | Q8T6J6 | Q8T6J6_PLAFA | Plasmodium falciparum | 4 | 0.7761 |
| Phosphodiesterase | Q8WQX9 | Q8WQX9_9TRYP | Trypanosoma brucei | 3 | 0.7760 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 3 | 0.7750 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7749 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7745 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7745 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7742 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7741 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7736 |
| C-1-tetrahydrofolate synthase, cytoplasmic | P11586 | C1TC_HUMAN | Homo sapiens | 3 | 0.7732 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7731 |
| Cellular tumor antigen p53 | P04637 | P53_HUMAN | Homo sapiens | 3 | 0.7718 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 3 | 0.7708 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7704 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | Q07422 | DRTS_TOXGO | Toxoplasma gondii | 3 | 0.7701 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7699 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7698 |
| Vitamin D3 dihydroxylase | P18326 | CPXE_STRGO | Streptomyces griseolus | 3 | 0.7697 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7694 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7694 |
| Tyrosine-protein kinase HCK | P08631 | HCK_HUMAN | Homo sapiens | 3 | 0.7685 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7652 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7637 |
| Cytochrome P450 130 | P9WPN5 | CP130_MYCTU | Mycobacterium tuberculosis | 3 | 0.7633 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7630 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7609 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7609 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7607 |
| Dihydrofolate reductase | P00374 | DYR_HUMAN | Homo sapiens | 3 | 0.7606 |
| Heat shock protein 75 kDa, mitochondrial | Q12931 | TRAP1_HUMAN | Homo sapiens | 3 | 0.7604 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7594 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.7593 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7587 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7581 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7580 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7570 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7570 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7568 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7565 |
| Pyruvate kinase PKM | P14618 | KPYM_HUMAN | Homo sapiens | 3 | 0.7564 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7553 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7541 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7538 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7538 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7536 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7535 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7526 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7522 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7518 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7517 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7514 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7507 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7502 |
| Antiviral protein I | P10297 | RIP1_PHYAM | Phytolacca americana | 4 | 0.7498 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7495 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7480 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7474 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7465 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7462 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7458 |
| DNA gyrase subunit B | Q839Z1 | GYRB_ENTFA | Enterococcus faecalis | 2 | 0.7451 |
| Cyclic AMP receptor protein | Q5SID7 | CRP_THET8 | Thermus thermophilus | 3 | 0.7449 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7447 |
| Aldehyde dehydrogenase, mitochondrial | P05091 | ALDH2_HUMAN | Homo sapiens | 3 | 0.7444 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7442 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7441 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7440 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7438 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 3 | 0.7437 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7434 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7433 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7423 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7421 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7401 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7399 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 3 | 0.7393 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7393 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 3 | 0.7392 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7391 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7389 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7388 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7386 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7386 |
| 16S rRNA (guanine(1405)-N(7))-methyltransferase | Q763K9 | Q763K9_ECOLX | Escherichia coli | 3 | 0.7370 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7366 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7364 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7360 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7359 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7356 |
| FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 2 | 0.7350 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7350 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.7348 |
| Histidine kinase 4 | Q9C5U0 | AHK4_ARATH | Arabidopsis thaliana | 3 | 0.7338 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7330 |
| Nitric oxide synthase 3 | P29474 | NOS3_HUMAN | Homo sapiens | 3 | 0.7330 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7325 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 3 | 0.7323 |
| Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7317 |
| Dihydrofolate reductase | P0A017 | DYR_STAAU | Staphylococcus aureus | 3 | 0.7310 |
| Beta-adrenergic receptor kinase 1 | P25098 | ARBK1_HUMAN | Homo sapiens | 3 | 0.7309 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7305 |
| Nicotinamide phosphoribosyltransferase | P43490 | NAMPT_HUMAN | Homo sapiens | 3 | 0.7289 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7287 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7282 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 2 | 0.7282 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7274 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7268 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7266 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 4 | 0.7264 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7259 |
| Adenylate cyclase 2 | A0A2U2H3Y1 | A0A384LKY8_YERPE | Yersinia pestis | 3 | 0.7256 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7253 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7252 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7248 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7243 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7243 |
| Orotidine 5'-phosphate decarboxylase | O26232 | PYRF_METTH | Methanothermobacter thermautotrophicus | 3 | 0.7242 |
| Proto-oncogene tyrosine-protein kinase Src | P12931 | SRC_HUMAN | Homo sapiens | 3 | 0.7234 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7227 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 2 | 0.7227 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7223 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 3 | 0.7221 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7218 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7215 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7212 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7205 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7202 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7202 |
| Methionine adenosyltransferase 2 subunit beta | Q9NZL9 | MAT2B_HUMAN | Homo sapiens | 4 | 0.7197 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 3 | 0.7196 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 4 | 0.7196 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7187 |
| ADP compounds hydrolase NudE | P45799 | NUDE_ECOLI | Escherichia coli | 2 | 0.7183 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.7180 |
| Cyclin-dependent kinase 6 | Q00534 | CDK6_HUMAN | Homo sapiens | 4 | 0.7169 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7164 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7164 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.7160 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7156 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7154 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7151 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7151 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7151 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7144 |
| Beta-secretase 2 | Q9Y5Z0 | BACE2_HUMAN | Homo sapiens | 2 | 0.7142 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7139 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 2 | 0.7131 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 3 | 0.7126 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7124 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7124 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | Q27793 | DRTS_TRYCR | Trypanosoma cruzi | 3 | 0.7119 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7118 |
| 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial | Q6NVY1 | HIBCH_HUMAN | Homo sapiens | 3 | 0.7117 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 2 | 0.7113 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 2 | 0.7112 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7111 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 2 | 0.7108 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7105 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 2 | 0.7105 |
| Polymerase basic protein 2 | Q2LG68 | Q2LG68_9INFA | Influenza A virus) | 4 | 0.7102 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7092 |
| GTPase KRas | P01116 | RASK_HUMAN | Homo sapiens | 3 | 0.7091 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.7090 |
| Actin-related protein 3 | P61157 | ARP3_BOVIN | Bos taurus | 3 | 0.7089 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 2 | 0.7087 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7087 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7086 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 4 | 0.7080 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 2 | 0.7076 |
| Ephrin type-A receptor 3 | P29320 | EPHA3_HUMAN | Homo sapiens | 3 | 0.7064 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7060 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7060 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7049 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7045 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7043 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7039 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7038 |
| Vitamin D3 receptor | P11473 | VDR_HUMAN | Homo sapiens | 4 | 0.7033 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 3 | 0.7032 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7031 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7029 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7026 |
| LD-carboxypeptidase | A0A6L8PVW7 | A0A1Q4LWC0_BACAN | Bacillus anthracis | 3 | 0.7024 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7024 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7016 |
| Serine/threonine-protein kinase toxin HipA | P23874 | HIPA_ECOLI | Escherichia coli | 2 | 0.7016 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7015 |
| Mitogen-activated protein kinase kinase kinase 7 | O43318 | M3K7_HUMAN | Homo sapiens | 3 | 0.7013 |
| Geranyl diphosphate 2-C-methyltransferase | D3KYU3 | GPPMT_STRLS | Streptomyces lasalocidi | 3 | 0.7013 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 4 | 0.7007 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 2 | 0.7006 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7002 |