5,8-dihydroxy-1-methylnaphtho[2,3c]furan-4,9-dione - Compound Card

5,8-dihydroxy-1-methylnaphtho[2,3c]furan-4,9-dione

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5,8-dihydroxy-1-methylnaphtho[2,3c]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles Oc1ccc(c2c1C(=O)c1c(C)occ1C2=O)O
InChI InChI=1S/C13H8O5/c1-5-9-6(4-18-5)12(16)10-7(14)2-3-8(15)11(10)13(9)17/h2-4,14-15H,1H3
InChIKey JYJNQZBODMZAMR-UHFFFAOYSA-N
Formula C13H8O5
HBA 5
HBD 2
MW 244.2
Rotatable Bonds 0
TPSA 87.74
LogP 1.77
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 244.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954
2 Bulbine capitata Asphodelaceae Plantae 576756

Showing of synonyms

  • Bezabih M, Abegaz BM, et al. (2001). Antiplasmodial and Antioxidant Isofuranonaphthoquinones from the Roots of Bulbine capitata. Planta medica, 2001, 67(4), 340–344. [View]
  • Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]
Pubchem: 135496998
Nmrshiftdb2: 60063502

No compound-protein relationship available.

Structure

SMILES: c1occ(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 244.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.650
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.890
Plasma Protein Binding
47.61
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.170
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.950
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.150
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)
2.570
Rat (Chronic Oral)
3.220
Fathead Minnow
4.230
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
398.440
Hydration Free Energy
-11.050
Log(D) at pH=7.4
2.080
Log(P)
2.98
Log S
-5.14
Log(Vapor Pressure)
-7.83
Melting Point
224.1
pKa Acid
5.08
pKa Basic
3.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9344
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9344
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9296
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.9296
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.9181
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.9181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9163
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9163
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9150
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.9150
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9135
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9135
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9107
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.9107
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.9097
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.9097
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9034
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9034
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8916
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8916
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8857
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8857
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8832
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8832
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8811
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8811
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8782
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8782
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8776
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8776
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8762
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8762
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8755
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8755
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8723
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8723
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8708
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8708
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8666
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8666
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8535
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8535
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8531
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8531
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8343
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.8343
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8335
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8335
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8310
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8310
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8259
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8259
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8224
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8224
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8180
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8154
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8154
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8113
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8113
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8004
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8004
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7968
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7968
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7968
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7968
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7944
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7944
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7888
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7888
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7799
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7799
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7760
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7760
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7754
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7754
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7742
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7742
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7719
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7719
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7719
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7719
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7717
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7717
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7715
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7715
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7701
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7701
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7693
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7693
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7692
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7692
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7688
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7688
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7676
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7676
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7634
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7634
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7617
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7617
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7600
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7600
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7589
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7589
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7576
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7576
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7576
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7576
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7574
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7574
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7552
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7552
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7541
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7541
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7525
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7525
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7515
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7496
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7496
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7492
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7492
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7489
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7489
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7473
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7473
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7461
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7461
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7455
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7455
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7450
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7450
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7442
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7442
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7438
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7438
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7429
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7429
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7404
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7404
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7401
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7401
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7399
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7399
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7387
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7387
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7368
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7368
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7358
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7358
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7345
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7345
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7342
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7342
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7339
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7339
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7324
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7324
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7321
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7320
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7320
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7320
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7320
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7315
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7315
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7299
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7299
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7289
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7289
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7287
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7287
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7284
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7284
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7259
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7259
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7243
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7243
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7236
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7236
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7234
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7234
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7221
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7221
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7192
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7192
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7186
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7186
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7182
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 4 0.7182
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7157
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7157
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7112
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7112
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7106
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7106
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7096
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7096
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7084
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7084
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7074
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7074
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7071
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7071
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7070
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7070
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7048
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7048
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7040
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7040
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7032
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7032
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7029
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7029
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7025
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7025
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7019
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7019

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