2-hydroxy-1,7,8-trimethoxypyrene - Compound Card

2-hydroxy-1,7,8-trimethoxypyrene

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2-hydroxy-1,7,8-trimethoxypyrene

Structure
Zoomed Structure
  • Family: Annonaceae
  • Kingdom: Plantae
  • Class: Phenanthrenoid
    • Subclass: Pyrene
Canonical Smiles COc1c(OC)cc2c3c1ccc1c3c(cc2)cc(c1OC)O
InChI InChI=1S/C19H16O4/c1-21-15-9-11-5-4-10-8-14(20)18(22-2)12-6-7-13(19(15)23-3)17(11)16(10)12/h4-9,20H,1-3H3
InChIKey WDTIUHCVSBKXKZ-UHFFFAOYSA-N
Formula C19H16O4
HBA 4
HBD 1
MW 308.33
Rotatable Bonds 3
TPSA 47.92
LogP 4.32
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 308.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Uvaria lucida ssp. lucida Annonaceae Plantae 509419

Showing of synonyms

  • Achenbach H, Höhn M, et al. (1997). Oxygenated pyrenes, their potential biosynthetic precursor and benzylated dihydroflavones from two African Uvaria species. Phytochemistry,1997,44(29),359-364. [View] [PubMed]
Pubchem: 10757180
Nmrshiftdb2: 70071394

No compound-protein relationship available.

Structure

SMILES: c12c3c4ccc1cccc2ccc3ccc4

Level: 0

Mol. Weight: 202.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.550
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.640
Plasma Protein Binding
75.87
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
8.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.030
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.550
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.480
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.480
Rat (Acute)
2.180
Rat (Chronic Oral)
2.410
Fathead Minnow
5.340
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
450.070
Hydration Free Energy
-8.050
Log(D) at pH=7.4
4.290
Log(P)
3.92
Log S
-6.16
Log(Vapor Pressure)
-6.98
Melting Point
132.46
pKa Acid
8.97
pKa Basic
3.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9642
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9642
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9298
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9298
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9210
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9210
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.9179
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.9179
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9148
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9148
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9083
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9083
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9074
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9074
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9046
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9046
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9007
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9007
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8942
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8942
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8901
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8901
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8856
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8856
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8839
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8839
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8807
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8807
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8797
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8797
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8768
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8768
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8735
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8735
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8713
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8713
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8711
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8711
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8694
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8694
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8688
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8688
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8665
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8665
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8632
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8632
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8623
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8623
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8620
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8620
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8584
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8584
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8583
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8583
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8560
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8560
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8480
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8480
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8468
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8468
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8466
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8466
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8418
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8418
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8410
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8410
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8359
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8359
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8342
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8342
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8338
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8338
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8330
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8330
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8313
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8313
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8300
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8300
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8240
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8240
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8207
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8207
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8200
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8200
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8188
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8188
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8186
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8186
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8168
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8157
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8157
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8128
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8128
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8125
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8125
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8122
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8122
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8116
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8116
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8109
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8109
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8098
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8098
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8082
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8082
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8060
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8060
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8033
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8033
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8031
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8031
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8026
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8026
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8001
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8001
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7965
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7965
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7947
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7947
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7941
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7941
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7923
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7923
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7916
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7916
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7912
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7912
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7878
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7878
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7874
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7874
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7858
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7858
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7854
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7854
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7842
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7842
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7841
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7841
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7839
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7839
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7829
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7829
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7776
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7776
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7759
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7759
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7758
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7758
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7735
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7735
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7726
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7726
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7717
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7717
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7717
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7717
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7710
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7710
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7685
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7685
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7682
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7682
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7678
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7678
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7634
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7634
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7621
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7621
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7607
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7607
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7591
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7591
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7588
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7588
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7578
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7578
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7571
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7571
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7569
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7569
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7541
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7541
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7539
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7539
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7533
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7533
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7517
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7517
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7509
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7509
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7497
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7497
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7481
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7481
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7479
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7479
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7477
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7477
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7476
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7476
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7475
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7475
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7471
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7471
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7461
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7461
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7460
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7460
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7458
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7458
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7458
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7429
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7429
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7424
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7424
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7400
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7400
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7393
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7393
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7393
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7393
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7390
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7390
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7387
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7387
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7362
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7362
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7359
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7359
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7327
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7327
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7319
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7319
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7318
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7318
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7313
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7313
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7292
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7292
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7292
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7292
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7286
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7286
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7265
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7265
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7261
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7261
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7257
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7257
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7252
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7252
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7238
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7238
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7214
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7214
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7202
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7202
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7202
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7202
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7200
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7200
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7198
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7198
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7198
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7198
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7191
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7191
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7191
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7191
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7187
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7187
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7182
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7182
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7174
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7174
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7172
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7172
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7169
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7169
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7163
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7163
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7160
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7158
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7158
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7152
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7152
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7149
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7149
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7140
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7112
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7112
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7111
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7111
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7105
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7105
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7097
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7097
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7070
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7070
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7058
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7058
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7055
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7055
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7052
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7052
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7052
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7052
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7051
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7051
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7038
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7038
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7035
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7035
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7034
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7034
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7023
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7023
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7018
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7018
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7017
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7017

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