1,5-dihydroxy-3-methoxyxanthone - Compound Card

1,5-dihydroxy-3-methoxyxanthone

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1,5-dihydroxy-3-methoxyxanthone

Structure
Zoomed Structure
  • Family: Gentianaceae, Clusiaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc(O)c2c(c1)oc1c(c2=O)cccc1O
InChI InChI=1S/C14H10O5/c1-18-7-5-10(16)12-11(6-7)19-14-8(13(12)17)3-2-4-9(14)15/h2-6,15-16H,1H3
InChIKey IQIGECASJMDDMD-UHFFFAOYSA-N
Formula C14H10O5
HBA 5
HBD 2
MW 258.23
Rotatable Bonds 1
TPSA 79.9
LogP 2.37
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 258.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Centaurium spicatum Gentianaceae Plantae 172074
2 Symphonia globulifera Clusiaceae Plantae 156483

Showing of synonyms

  • El-Shanawany MA, Mohamed GA, et al. (2011). A new xanthone from the roots of Centaurium spicatum. Phytochemistry Letters,2011,4,126-128. [View]
  • Nguengang RT, Tchegnitegni BT, et al. (2023). Constituents of the Stem Bark of Symphonia globulifera Linn. f. with Antileishmanial and Antibacterial Activities. Molecules. 2023, 28(6), 2473. [View] [PubMed]
Pubchem: 5281651
Kegg Ligand: C10081
Chebi: 6785
Nmrshiftdb2: 60070191
Metabolights: MTBLC6785
Bindingdb: 50155425

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 196.21 g/mol

Antimicrobial
Antiprotozoal
Cytotoxicity

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.370
Plasma Protein Binding
72.24
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
2.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.390
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.800
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.320
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.490
Rat (Acute)
2.100
Rat (Chronic Oral)
2.660
Fathead Minnow
4.570
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
404.430
Hydration Free Energy
-10.530
Log(D) at pH=7.4
2.750
Log(P)
3.11
Log S
-4.66
Log(Vapor Pressure)
-6.94
Melting Point
226.75
pKa Acid
7.34
pKa Basic
3.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9583
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9583
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9429
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9429
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9401
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9401
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9390
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9390
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9358
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9358
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9290
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9290
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9174
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9174
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9172
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9172
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9149
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9149
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9090
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9090
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.9012
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.9012
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8990
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8990
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8974
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8974
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8969
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8969
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8952
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8952
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8906
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8906
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8872
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8872
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8847
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8847
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8808
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8808
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8789
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8789
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8736
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8736
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8721
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8721
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8719
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8719
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8703
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8703
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8687
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8687
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8681
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8681
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8606
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8606
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8571
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8571
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8548
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8548
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8527
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8527
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8519
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8519
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8420
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8420
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8383
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8383
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8338
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8338
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8328
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8328
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8318
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8318
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8305
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8305
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8238
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8238
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8235
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8235
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.8209
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.8209
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8192
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8192
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8149
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8149
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8136
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8136
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8127
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8127
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8118
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8118
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8065
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8065
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8057
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8057
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8021
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8021
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8021
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8021
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8009
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8009
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7990
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7990
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7976
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7976
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7973
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7973
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7969
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7969
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7967
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7967
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7954
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7954
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7883
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7883
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7876
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7876
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7871
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7871
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7869
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7869
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7850
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7850
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7823
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7823
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7818
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7818
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7816
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7816
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7807
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7807
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7805
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7805
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7786
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7786
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7749
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7749
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7735
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7735
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7731
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7731
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7672
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7672
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7666
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7666
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7660
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7660
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7658
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7658
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7645
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7645
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7622
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7622
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7618
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7618
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7612
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7612
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7603
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7603
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7589
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7589
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7575
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7575
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7546
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7546
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7544
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7544
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7535
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7535
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7526
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7526
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7523
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7523
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7517
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7517
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7513
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7513
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7507
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7507
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7504
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7504
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7496
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7496
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7495
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7495
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7489
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7489
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7484
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7484
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7472
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7472
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7471
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7471
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7459
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7459
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7446
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7446
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7444
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7444
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7440
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7440
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7439
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7439
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7431
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7431
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7430
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7430
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7416
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7416
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7413
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7413
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7410
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7410
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7410
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7410
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7409
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7409
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7407
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7407
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7406
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7406
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7402
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7402
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7395
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7395
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7389
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7389
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7386
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7386
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7371
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7371
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7365
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7365
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7364
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7364
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7350
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7350
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7347
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7347
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7339
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7339
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7324
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7324
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7307
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7307
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7292
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7292
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7290
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7290
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7288
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7288
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7287
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7287
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7287
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7287
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7281
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7281
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7270
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7270
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7264
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7264
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7254
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7254
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7254
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7254
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7253
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7253
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7248
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7248
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7248
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7248
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7247
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7247
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7246
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7246
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7245
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7245
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7240
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7240
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7237
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 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
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7234
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7234
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7232
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7232
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7226
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7226
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7225
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7225
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7219
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7219
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7201
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7201
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7201
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7201
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7198
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7198
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7172
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7172
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7171
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7171
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7170
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7170
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7160
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7147
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7147
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7140
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7140
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7130
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7130
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7118
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7118
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7110
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7110
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7103
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7103
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7092
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7092
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7091
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7091
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7088
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7088
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7084
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7084
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7080
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7080
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7078
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7078
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7070
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7070
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7070
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7070
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7069
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7062
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7062
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7058
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7058
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7057
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7057
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7054
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7054
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7052
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7052
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7051
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7051
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7049
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7049
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7044
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7044
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7030
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7030
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7029
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 4 0.7029
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7017
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7017
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7016
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7016
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7008
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7008
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7007
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7007
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7005
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7005

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