2-hydroxy-3-methoxyxanthone - Compound Card

2-hydroxy-3-methoxyxanthone

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2-hydroxy-3-methoxyxanthone

Structure
Zoomed Structure
  • Family: Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Xanthone Derivative
Canonical Smiles COc1cc2oc3ccccc3c(=O)c2cc1O
InChI InChI=1S/C14H10O4/c1-17-13-7-12-9(6-10(13)15)14(16)8-4-2-3-5-11(8)18-12/h2-7,15H,1H3
InChIKey ZXVAPEXGRPGWCF-UHFFFAOYSA-N
Formula C14H10O4
HBA 4
HBD 1
MW 242.23
Rotatable Bonds 1
TPSA 59.67
LogP 2.66
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 242.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum riparium Hypericaceae Plantae 269018

Showing of synonyms

  • Tala MF, Talontsi FM, et al. (2015). Antimicrobial and cytotoxic constituents from native Cameroonian medicinal plant Hypericum riparium.. Fitoterapia,2015, 102, 149-155. [View] [PubMed]
Pubchem: 12214327
Nmrshiftdb2: 70013534

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 196.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.180
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.280
Plasma Protein Binding
77.34
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.920
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.950
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.600
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
Safe
T. Pyriformis
4.450
Rat (Acute)
1.840
Rat (Chronic Oral)
2.320
Fathead Minnow
4.680
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
392.040
Hydration Free Energy
-10.340
Log(D) at pH=7.4
2.770
Log(P)
2.82
Log S
-4.31
Log(Vapor Pressure)
-7.1
Melting Point
197.81
pKa Acid
6.3
pKa Basic
3.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9684
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9481
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9441
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.9429
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9411
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9374
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9351
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9342
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9306
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9192
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9048
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8942
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8931
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8914
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8854
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8820
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8809
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8806
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8786
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8756
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8742
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8683
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8678
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8612
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8601
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8597
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8573
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8524
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8496
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8455
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8453
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.8421
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8407
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.8398
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8388
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8378
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 3 0.8372
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8359
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8322
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8317
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8288
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8264
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.8259
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8198
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8194
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8106
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8082
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8073
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8065
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8056
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8039
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8036
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8028
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8025
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8013
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 3 0.8009
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7998
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7986
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7984
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7960
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.7957
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7934
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7913
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7897
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7897
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7889
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7865
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7863
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7852
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7845
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7844
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7837
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7825
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7814
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7806
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7802
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7797
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7789
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7741
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7736
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7728
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7715
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7694
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7694
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7692
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7690
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7671
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7666
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7662
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7656
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7655
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7655
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7653
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7648
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7637
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7634
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7630
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7629
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7629
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7627
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7608
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7607
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7601
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7600
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7581
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7573
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7573
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7562
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7536
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7530
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7527
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7523
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7516
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7515
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7513
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7498
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7492
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7490
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7489
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7484
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7482
Envelope glycoprotein gp160 Q0ED31 Q0ED31_9HIV1 Human immunodeficiency virus 1 3 0.7479
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7479
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7478
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7470
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7455
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7455
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7450
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7448
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7426
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7425
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7424
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7418
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7418
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7413
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7411
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7404
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7400
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7394
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7391
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7386
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7384
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7382
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7377
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7377
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7366
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7350
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7349
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 4 0.7347
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7347
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7339
Tubulin alpha chain A0A0R4I993 A0A0R4I993_SUSBA Sus barbatus 3 0.7335
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 2 0.7333
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 2 0.7328
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7328
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7326
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7324
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7319
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7316
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7305
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7303
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7299
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7297
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7288
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7283
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7283
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7281
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7281
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7268
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7263
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7262
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7261
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7261
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7260
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7258
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7241
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7237
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7237
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7225
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7223
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7219
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7213
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7205
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7202
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7201
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7200
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7196
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7195
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7191
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7190
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7183
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7183
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7183
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7175
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7164
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7162
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7160
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7159
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7158
Bifunctional dihydrofolate reductase-thymidylate synthase D9N170 D9N170_PLAFA Plasmodium falciparum 3 0.7158
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7152
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7152
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7149
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7143
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7141
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7137
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7129
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7128
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7127
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 4 0.7124
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7116
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7112
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7104
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7098
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7094
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 2 0.7083
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7080
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7073
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7068
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7067
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7064
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7064
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7062
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7060
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7058
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7058
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7056
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7056
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Q9NTG7 SIR3_HUMAN Homo sapiens 4 0.7050
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7043
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7038
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7037
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7036
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7035
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7031
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7024
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7020
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7020
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7014
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7014
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 4 0.7012
Ribosomal RNA small subunit methyltransferase Nep1 Q57977 NEP1_METJA Methanocaldococcus jannaschii 3 0.7008
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7006
Thymidylate kinase Q9HZN8 KTHY_PSEAE Pseudomonas aeruginosa 3 0.7001

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