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Norsanguinarine
- Family: Plantae - Papaveraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | C1Oc2c(O1)cc1c(c2)ccc2c1ncc1c2ccc2c1OCO2 |
|---|---|
| InChI | InChI=1S/C19H11NO4/c1-2-12-11-3-4-15-19(24-9-21-15)14(11)7-20-18(12)13-6-17-16(5-10(1)13)22-8-23-17/h1-7H,8-9H2 |
| InChIKey | CNXVDVMAYXLWPD-UHFFFAOYSA-N |
| Formula | C19H11NO4 |
| HBA | 5 |
| HBD | 0 |
| MW | 317.3 |
| Rotatable Bonds | 0 |
| TPSA | 49.81 |
| LogP | 4.0 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.11 |
| Exact Mass | 317.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Glaucium arabicum | Papaveraceae | Plantae | 2072396 |
Showing of synonyms
Norsanguinarine
522-30-5
Sanguinarine, 13-demethyl-
(1,3)Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridine
1,3-Dioxolo[i][1,3]dioxolo[4,5]benzo[1,2-c]phenanthridine
5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
NSC 143762
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridine
1,3-Dioxolo(i)(1,3)dioxolo(4,5)benzo(1,2-c)phenanthridine
5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene
5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.0^(2,10).0^(4,8).0^(14,22).0^(17,21))tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaene
5,7,18,20-tetraoxa-24-azahexacyclo(11.11.0.02,10.04,8.014,22.017,21)tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
Cnxvdvmayxlwpd-uhfffaoysa-n
[1,3]Dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridine
5157-23-3
13-Demethyl-Sanguinarine
CHEMBL4751586
SCHEMBL16125304
DTXSID90965891
CHEBI:179641
NSC143762
AKOS030535106
FS-8003
NSC-143762
HY-123077
NS00093944
[1,6-c]-1,3-dioxolo[4,5-i]phenanthridine
7,8-Bis(methylenedioxy)benzo[c]phenanthridine
1,3]dioxolo[4,5]benzo[1,2-c]phenanthridine
2H,10H-[1,3]Benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridine
5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0(2),(1)?.0?,?.0(1)?,(2)(2).0(1)?,(2)(1)]tetracosa-1(13),2(10),3,8,11,14(22),15,17(21),23-nonaene
- Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]
Pubchem:
97679
Cas:
522-30-5
Zinc:
ZINC000001727527
Chebi:
179641
Nmrshiftdb2:
60032606
Chembl:
CHEMBL4751586
No compound-protein relationship available.
SMILES: O1COc(c12)ccc3c2cnc4c3ccc5c4cc6c(c5)OCO6
Level: 0
Mol. Weight: 317.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.26
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.44
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.76
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.74
- Plasma Protein Binding
- 82.8
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- 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
- Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.49
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.3
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.42
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.62
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -1.01
- Rat (Acute)
- 2.51
- Rat (Chronic Oral)
- 1.46
- Fathead Minnow
- 5.38
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 510.54
- Hydration Free Energy
- -6.99
- Log(D) at pH=7.4
- 3.47
- Log(P)
- 4.46
- Log S
- -5.79
- Log(Vapor Pressure)
- -10.19
- Melting Point
- 234.55
- pKa Acid
- 10.21
- pKa Basic
- 2.92
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9826 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.9648 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.9622 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.9502 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.9439 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.9405 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9389 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9379 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9374 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9314 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.9310 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9215 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 4 | 0.9171 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.9170 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9134 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.9127 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 3 | 0.9091 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.9067 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.9013 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9009 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8963 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8950 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.8948 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8948 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8909 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8880 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8872 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8848 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8838 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8837 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8823 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8794 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8789 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8774 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8768 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.8732 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8727 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.8710 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.8696 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8684 |
| Steroid C26-monooxygenase | P9WPP1 | CP125_MYCTU | Mycobacterium tuberculosis | 3 | 0.8671 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8665 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8654 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8634 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8629 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.8607 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8594 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8569 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 4 | 0.8542 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8517 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 4 | 0.8516 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8416 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8410 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8401 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8379 |
| Alpha-1-acid glycoprotein 2 | P19652 | A1AG2_HUMAN | Homo sapiens | 3 | 0.8375 |
| Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8375 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.8373 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8295 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.8290 |
| Tubulin alpha chain | D0VWZ0 | D0VWZ0_SHEEP | Ovis aries | 4 | 0.8289 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8287 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8258 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8241 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8220 |
| Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase | Q46381 | BPHB_COMTE | Comamonas testosteroni | 3 | 0.8157 |
| Proliferating cell nuclear antigen | P12004 | PCNA_HUMAN | Homo sapiens | 3 | 0.8145 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8132 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8044 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8024 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8007 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7979 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7967 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7964 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7955 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7946 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7938 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7930 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7926 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.7924 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 4 | 0.7920 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 3 | 0.7920 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7879 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7873 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7844 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7842 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 3 | 0.7835 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 4 | 0.7814 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7813 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7802 |
| Estrogen receptor beta | Q92731 | ESR2_HUMAN | Homo sapiens | 4 | 0.7795 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7774 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7752 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7744 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 3 | 0.7735 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7726 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7721 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7673 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 4 | 0.7663 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7659 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7614 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7602 |
| Cyclic nucleotide-binding protein | B8FW11 | B8FW11_DESHD | Desulfitobacterium hafniense | 3 | 0.7593 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7579 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7569 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7565 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7564 |
| Phosphodiesterase | Q8WQX9 | Q8WQX9_9TRYP | Trypanosoma brucei | 3 | 0.7563 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7556 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7556 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7553 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.7541 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7536 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7532 |
| Beta-2 adrenergic receptor | P07550 | ADRB2_HUMAN | Homo sapiens | 2 | 0.7517 |
| Cytochrome P450 2B4 | P00178 | CP2B4_RABIT | Oryctolagus cuniculus | 3 | 0.7516 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7513 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7512 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7499 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7495 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7477 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.7472 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7466 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7461 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7454 |
| Dual specificity protein kinase TTK | P33981 | TTK_HUMAN | Homo sapiens | 3 | 0.7453 |
| Nuclear receptor coactivator 2 | Q15596 | NCOA2_HUMAN | Homo sapiens | 3 | 0.7447 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7443 |
| Sterol 14alpha-demethylase | P9WPP9 | CP51_MYCTU | Mycobacterium tuberculosis | 4 | 0.7440 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7434 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 4 | 0.7431 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7426 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7422 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7418 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7416 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 3 | 0.7412 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7411 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7407 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7405 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7389 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 2 | 0.7388 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7369 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7367 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 4 | 0.7359 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7351 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7342 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7335 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7319 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7306 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7304 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 2 | 0.7290 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7251 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7249 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7249 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7235 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7230 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7226 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7224 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7213 |
| Bromodomain protein, putative | Q8I240 | Q8I240_PLAF7 | Plasmodium falciparum | 4 | 0.7210 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7208 |
| Focal adhesion kinase 1 | Q05397 | FAK1_HUMAN | Homo sapiens | 3 | 0.7198 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 4 | 0.7195 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7179 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 3 | 0.7157 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7156 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7149 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7139 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7138 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7134 |
| Hexokinase-4 | P35557 | HXK4_HUMAN | Homo sapiens | 3 | 0.7124 |
| tyrosine--tRNA ligase | Q4QFJ7 | Q4QFJ7_LEIMA | Leishmania major | 3 | 0.7120 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 4 | 0.7117 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7114 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7098 |
| Aminoglycoside 3'-phosphotransferase AphA1-IAB | B0VD92 | B0VD92_ACIBY | Acinetobacter baumannii | 3 | 0.7084 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 4 | 0.7078 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7066 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7063 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7050 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7046 |
| ALK tyrosine kinase receptor | Q9UM73 | ALK_HUMAN | Homo sapiens | 4 | 0.7015 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7010 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7010 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7008 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 2 | 0.7005 |