3-geranyl-2,4,6-trihydroxybenzophenone - Compound Card

3-geranyl-2,4,6-trihydroxybenzophenone

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3-geranyl-2,4,6-trihydroxybenzophenone

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles C/C(=C\Cc1c(O)cc(c(c1O)C(=O)c1ccccc1)O)/CCC=C(C)C
InChI InChI=1S/C23H26O4/c1-15(2)8-7-9-16(3)12-13-18-19(24)14-20(25)21(23(18)27)22(26)17-10-5-4-6-11-17/h4-6,8,10-12,14,24-25,27H,7,9,13H2,1-3H3/b16-12+
InChIKey ZAIQNYMNZNXUAF-FOWTUZBSSA-N
Formula C23H26O4
HBA 4
HBD 3
MW 366.46
Rotatable Bonds 7
TPSA 77.76
LogP 5.27
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 366.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Fobofou SA, Franke K, et al. (2015). Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.. Bioorganic & medicinal chemistry,2015, 23(19), 6327-6334. [View] [PubMed]
Pubchem: 6477676
Chebi: 65958
Nmrshiftdb2: 60031281
Metabolights: MTBLC65958

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 366.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 366.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
71.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.45
Micronucleos
Toxic
NR-AhR
Safe
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
0.66
Rat (Acute)
2.05
Rat (Chronic Oral)
3.13
Fathead Minnow
5.33
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
422.96
Hydration Free Energy
-10.87
Log(D) at pH=7.4
4.04
Log(P)
6.83
Log S
-6.16
Log(Vapor Pressure)
-8.11
Melting Point
120.15
pKa Acid
7.43
pKa Basic
7.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9607
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9546
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9428
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9378
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9298
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9220
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9208
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9186
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.9175
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.9091
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.9046
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9035
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9026
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9001
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8998
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8967
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8959
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.8938
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8915
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.8909
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8828
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8828
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8800
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8770
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.8768
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8728
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8710
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8704
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8644
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8593
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8586
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8576
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8512
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8480
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8478
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8474
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8466
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8426
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8425
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8412
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8403
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8370
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8345
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 4 0.8329
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 3 0.8324
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8311
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8309
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 5 0.8306
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8299
Calmodulin-domain protein kinase 1, putative A3FQ16 A3FQ16_CRYPI Cryptosporidium parvum 4 0.8291
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.8281
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8281
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8266
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8258
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8235
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8224
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.8217
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8199
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8196
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8182
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8180
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8180
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8166
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8159
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8129
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8097
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8096
Cytochrome P450 130 P9WPN5 CP130_MYCTU Mycobacterium tuberculosis 3 0.8088
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8087
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8073
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8070
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8061
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.8031
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8009
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.8009
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8000
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7993
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7992
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7981
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7980
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7978
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7938
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7916
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7893
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7890
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7884
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.7877
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7855
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7831
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7830
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7822
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7821
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7816
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7795
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7775
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7771
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7766
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7765
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7758
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7745
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7745
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7741
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7725
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7710
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7706
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7706
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7705
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7703
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7694
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7685
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7683
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7672
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7665
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7661
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7656
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7641
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7638
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7635
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7630
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7627
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7621
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7615
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7614
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7612
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7611
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7603
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7598
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7594
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7592
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7592
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7585
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7583
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7577
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7576
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7574
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7569
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7567
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7557
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7551
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7549
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7546
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7537
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7537
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7535
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7530
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7527
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7520
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7512
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7504
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7499
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7497
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7497
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7487
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7485
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7470
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7467
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7467
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7463
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7457
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7456
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7454
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7453
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7451
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7451
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7440
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7430
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7428
Uncharacterized protein C7YVL8 C7YVL8_NECH7 Nectria haematococca 3 0.7426
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7423
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7423
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7420
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7420
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7419
Bifunctional dihydrofolate reductase-thymidylate synthase D9N170 D9N170_PLAFA Plasmodium falciparum 4 0.7414
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7412
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7407
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7402
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7402
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7400
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7393
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7391
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7386
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 3 0.7384
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7368
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7366
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7364
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7361
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7360
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7358
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7357
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7354
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7350
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.7348
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7348
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7346
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7344
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7344
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7342
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7341
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7339
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7335
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7333
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7333
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7326
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7322
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7318
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7312
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7312
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7306
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7302
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7302
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7296
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7296
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7295
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7292
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7292
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial P08559 ODPA_HUMAN Homo sapiens 3 0.7290
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 4 0.7284
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7280
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 4 0.7274
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7274
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7263
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P9WK11 MEND_MYCTU Mycobacterium tuberculosis 3 0.7260
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7260
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7260
Transthyretin P02766 TTHY_HUMAN Homo sapiens 3 0.7259
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 4 0.7258
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7256
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7252
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7251
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7249
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7241
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7241
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7234
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7234
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7231
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7228
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7228
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7225
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7223
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7222
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7220
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7218
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7216
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7215
Thiamine-binding periplasmic protein P31550 THIB_ECOLI Escherichia coli 3 0.7214
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7212
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7212
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7209
Thiamin pyrophosphokinase 1 Q9R0M5 TPK1_MOUSE Mus musculus 3 0.7207
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7206
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7202
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7201
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7198
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7188
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7187
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7186
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7179
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 2 0.7179
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7179
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7177
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7163
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7162
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7162
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7162
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7159
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7159
Pyruvate dehydrogenase E1 component P0AFG8 ODP1_ECOLI Escherichia coli 3 0.7156
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7149
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7148
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7147
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7147
Multifunctional 2-oxoglutarate metabolism enzyme A0R2B1 KGD_MYCS2 Mycolicibacterium smegmatis155) 3 0.7146
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7145
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7145
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7144
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.7143
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.7139
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7137
N(2)-(2-carboxyethyl)arginine synthase Q9LCV9 CEAS_STRCL Streptomyces clavuligerus 3 0.7133
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7130
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 2 0.7123
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7120
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7118
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7115
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7114
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7113
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7100
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7098
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7097
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7093
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7092
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7089
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7088
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7086
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7086
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7084
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7083
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7082
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7081
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 4 0.7081
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 4 0.7080
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7076
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7061
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7057
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7054
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7049
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7049
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7049
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7047
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7046
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7046
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 4 0.7045
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7042
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7039
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7038
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7034
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7032
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7030
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7027
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7027
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7023
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7020
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7015
Pyruvate decarboxylase isozyme 1 P06169 PDC1_YEAST Saccharomyces cerevisiae 3 0.7013
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7011
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7008
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7007
V-1 PROTEASE protein Q9Q288 Q9Q288_9HIV1 Human immunodeficiency virus 1 3 0.7004
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7003
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7001

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