2,7-dihydroxy-1,8-dimethoxypyrene - Compound Card

2,7-dihydroxy-1,8-dimethoxypyrene

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2,7-dihydroxy-1,8-dimethoxypyrene

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Phenanthrenoid
    • Subclass: Pyrene
Canonical Smiles COc1c(O)cc2c3c1ccc1c3c(cc2)cc(c1OC)O
InChI InChI=1S/C18H14O4/c1-21-17-11-5-6-12-16-10(8-14(20)18(12)22-2)4-3-9(15(11)16)7-13(17)19/h3-8,19-20H,1-2H3
InChIKey GCHNQYKYNHGZKM-UHFFFAOYSA-N
Formula C18H14O4
HBA 4
HBD 2
MW 294.31
Rotatable Bonds 2
TPSA 58.92
LogP 4.01
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.11
Exact Mass 294.09
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: 10613704
Nmrshiftdb2: 70071392

No compound-protein relationship available.

Structure

SMILES: c12c3c4ccc1cccc2ccc3ccc4

Level: 0

Mol. Weight: 294.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.520
Plasma Protein Binding
75.94
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
5.680
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.650
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.990
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
2.000
Rat (Acute)
2.100
Rat (Chronic Oral)
3.010
Fathead Minnow
5.110
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
435.050
Hydration Free Energy
-8.900
Log(D) at pH=7.4
3.680
Log(P)
3.74
Log S
-5.91
Log(Vapor Pressure)
-6.87
Melting Point
186.29
pKa Acid
8.04
pKa Basic
3.55
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 0.9579
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9579
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9277
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9277
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9176
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9176
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9151
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.9151
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9032
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9032
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9019
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9019
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8980
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8980
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8954
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8954
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8830
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8830
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8823
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8823
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8800
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8800
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8773
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8773
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8664
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8664
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8628
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8628
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8600
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8600
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8588
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8588
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8575
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8575
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8560
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8560
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8547
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8547
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8542
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8500
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8500
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8467
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8467
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8424
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.8424
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8413
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8413
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8410
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8410
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8381
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8381
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8358
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8358
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8340
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8340
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8302
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8302
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8298
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8298
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8281
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8281
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8235
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8235
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8212
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8212
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8176
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8176
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8159
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8159
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8125
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.8125
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8118
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8118
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8103
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8103
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8089
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8089
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8085
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8085
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8083
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8083
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8014
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8014
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7977
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7977
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7947
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7947
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7946
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7946
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7932
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7932
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7926
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7926
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7925
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7925
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7879
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7879
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7851
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7851
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7846
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7846
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7843
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7843
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7838
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7838
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7830
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7830
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7818
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7818
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7815
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7815
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7795
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7795
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7795
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7795
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7788
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7788
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7782
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7782
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7775
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7775
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7774
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7774
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7747
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7747
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7720
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7720
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7681
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7681
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7673
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7673
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7665
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7665
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7639
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.7639
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7636
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7636
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7624
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7624
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7595
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7595
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7583
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7583
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7578
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7578
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7575
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7575
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7573
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7573
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7558
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7558
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7553
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7553
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7546
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7546
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7514
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7514
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7482
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7482
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7477
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7477
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7476
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7476
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7463
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7463
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7417
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7417
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7391
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7391
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7385
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7385
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7362
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7362
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7356
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7356
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7335
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7335
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7334
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7334
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7325
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7325
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7322
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7322
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7311
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7311
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7309
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7309
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7295
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7295
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7284
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7284
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7272
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7272
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7267
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7267
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7260
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7260
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7253
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7253
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7249
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7249
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7247
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7247
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7243
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7243
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7237
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7237
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7236
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7236
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7233
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7233
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7230
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7230
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7223
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7223
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7222
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7222
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7208
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7208
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7206
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7206
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7198
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7198
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7193
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7193
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7185
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7185
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7160
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7160
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7155
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7155
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7150
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7150
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7147
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7147
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7143
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7143
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7137
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7137
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7123
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7122
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7122
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7117
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7117
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7111
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7111
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7104
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7104
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7104
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7104
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7103
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7103
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7098
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7098
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7086
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7086
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7069
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7069
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7068
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7068
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7058
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7058
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7047
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7047
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7033
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7033
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7033
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7033
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7029
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7029
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7006
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7006

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