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3,4-dicaffeoylquinic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Hydroxycinnamic Acid
| Canonical Smiles | O=C(O[C@@H]1[C@H](O)C[C@@](C[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)(O)C(=O)O)/C=C/c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1 |
| InChIKey | UFCLZKMFXSILNL-PSEXTPKNSA-N |
| Formula | C25H24O12 |
| HBA | 11 |
| HBD | 7 |
| MW | 516.46 |
| Rotatable Bonds | 7 |
| TPSA | 211.28 |
| LogP | 1.03 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 37 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 516.13 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Cynara scolymus | Asteraceae | Plantae | 59895 |
| 2 | Cotula cinerea | Asteraceae | Plantae | — |
Showing of synonyms
3,4-dicaffeoylquinic acid
4,5-Dicqa
4,5-Dicaffeoylquinic acid
89886-31-7
45777W94HK
UNII-45777W94HK
Cyclohexanecarboxylic acid, 3,4-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,5-dihydroxy-, (1S,3R,4R,5R)-
Isochlorogenic acid b
14534-61-3
(1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
3,4-Di-O-Caffeoylquinic acid
CHEBI:5995
CHEMBL249448
Cyclohexanecarboxylic acid, 3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,5-dihydroxy-, (1S,3R,4R,5R)-
Cyclohexanecarboxylic acid, 3,4-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,5-dihydroxy-, (1S,3R,4R,5R)-
IsochlorogenicacidB
102851-07-0
Isochlorogenic-acid-B
3,4-dicaffeoylquinate
Isochlorogenic acid B?
3,4-Dicaffeoylquinicacid
Rel-3,4-Dicaffeoylquinic Acid
4,5-Di-O-caffeoylquinic acid?
Quinic acid 3,4-di-O-caffeate
SCHEMBL12246115
ACon1_002212
GTPL12549
HY-N0057R
GLXC-13081
(1S,3R,4R,5R)-3,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
HY-N0057
MSK15168
BDBM50362838
S9274
3,4-Dicaffeoylquinic acid (Standard)
AKOS026673963
CCG-269822
CS-3769
FD40706
NCGC00179718-01
1ST15168
AS-74985
NS00097363
Q27106970
3,4-Di-O-caffeoylquinic acid, >=90% (LC/MS-ELSD)
(1S,3R,4R,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid
(1S,3R,4R,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid
- Hammouda FM, Seif El-Nesr MM, et al. (1991). HPLC evaluation of the active constituents in the newly introduced romanian strain of Cynara scolymus cultivated in Egypt. Planta Medica,1991,57(2),A119-A120. [View]
- Khallouki F, Sellam K, et al. (2015). Phytoconstituents and in vitro evaluation of antioxidant capacities of Cotula cinerea (Morocco) methanol extracts. Records of Natural Products,2015,9(4),572-575. [View]
Pubchem:
5281780
Cas:
89886-31-7
Gnps:
CCMSLIB00000081759
Zinc:
ZINC000004098735
Kegg Ligand:
C10468
Chebi:
5995
Nmrshiftdb2:
60022364
Metabolights:
MTBLC5995
Chembl:
CHEMBL249448
Bindingdb:
50362838
CPRiL:
85602
SMILES: c1ccccc1C=CC(=O)OC2C(CCCC2)OC(=O)C=Cc3ccccc3
Level: 2
Mol. Weight: 516.46 g/mol
SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 516.46 g/mol
SMILES: C1CCCCC1
Level: 0
Mol. Weight: 516.46 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 516.46 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -6.58
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.59
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -3.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.79
- Plasma Protein Binding
- 71.54
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.65
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.08
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.64
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.23
- 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
- -457.62
- Rat (Acute)
- 2.18
- Rat (Chronic Oral)
- 3.9
- Fathead Minnow
- 4.14
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 603.97
- Hydration Free Energy
- -2.56
- Log(D) at pH=7.4
- -0.14
- Log(P)
- 1.56
- Log S
- -2.4
- Log(Vapor Pressure)
- -14.7
- Melting Point
- 256.06
- pKa Acid
- 4.51
- pKa Basic
- 6.27
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9355 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9355 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9129 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9129 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9086 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9086 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9074 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9074 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8750 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8750 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8720 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8720 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8683 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8683 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8619 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8619 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8491 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8491 |
| Bis(5'-adenosyl)-triphosphatase | P49789 | FHIT_HUMAN | Homo sapiens | 3 | 0.8459 |
| Bis(5'-adenosyl)-triphosphatase | P49789 | FHIT_HUMAN | Homo sapiens | 3 | 0.8459 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8459 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8459 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8349 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8349 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.8326 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.8326 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.8271 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.8271 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8265 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8265 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.8261 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.8261 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 3 | 0.8239 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 3 | 0.8239 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8192 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8192 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8184 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8184 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8124 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8124 |
| Ectonucleoside triphosphate diphosphohydrolase I | Q5ZUA2 | Q5ZUA2_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.8089 |
| Ectonucleoside triphosphate diphosphohydrolase I | Q5ZUA2 | Q5ZUA2_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.8089 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8084 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8084 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8065 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8065 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8005 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8005 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7993 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7993 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7982 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7982 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7908 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7908 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7884 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7884 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7833 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7833 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7805 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7805 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7799 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7799 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | B1MKD5 | B1MKD5_MYCA9 | Mycobacteroides abscessus | 3 | 0.7791 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | B1MKD5 | B1MKD5_MYCA9 | Mycobacteroides abscessus | 3 | 0.7791 |
| Aspartate carbamoyltransferase catalytic subunit | P0A786 | PYRB_ECOLI | Escherichia coli | 3 | 0.7752 |
| Aspartate carbamoyltransferase catalytic subunit | P0A786 | PYRB_ECOLI | Escherichia coli | 3 | 0.7752 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 4 | 0.7752 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 4 | 0.7752 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7748 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7748 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7674 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7674 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7645 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7645 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 4 | 0.7621 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 4 | 0.7621 |
| Aspartate carbamoyltransferase catalytic subunit | P0A786 | PYRB_ECOLI | Escherichia coli | 3 | 0.7614 |
| Aspartate carbamoyltransferase catalytic subunit | P0A786 | PYRB_ECOLI | Escherichia coli | 3 | 0.7614 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7603 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7603 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7573 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7573 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7555 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7555 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7544 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7544 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7525 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7525 |
| 5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase | Q8U0R7 | PURP_PYRFU | Pyrococcus furiosus | 3 | 0.7501 |
| 5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase | Q8U0R7 | PURP_PYRFU | Pyrococcus furiosus | 3 | 0.7501 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7500 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7500 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7499 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7499 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7495 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7495 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7473 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7473 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7433 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7433 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7422 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7422 |
| Chemotaxis protein CheA | Q56310 | CHEA_THEMA | Thermotoga maritima | 3 | 0.7413 |
| Chemotaxis protein CheA | Q56310 | CHEA_THEMA | Thermotoga maritima | 3 | 0.7413 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7407 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7407 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7384 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7384 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7355 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7355 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7348 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7348 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7306 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7306 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7294 |
| Nickel-binding periplasmic protein | P33590 | NIKA_ECOLI | Escherichia coli | 2 | 0.7294 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7288 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7288 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7279 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7279 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7273 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7273 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7243 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7243 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 4 | 0.7241 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 4 | 0.7241 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7234 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7234 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7229 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7229 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7214 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7214 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7214 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7214 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7203 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7203 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7193 |
| Glucose-1-phosphate adenylyltransferase small subunit, chloroplastic/amyloplastic | P23509 | GLGS_SOLTU | Solanum tuberosum | 3 | 0.7193 |
| Glucose-1-phosphate adenylyltransferase small subunit, chloroplastic/amyloplastic | P23509 | GLGS_SOLTU | Solanum tuberosum | 3 | 0.7193 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7193 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7172 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7172 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7160 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7160 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7159 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7159 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7158 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7158 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7158 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7158 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7158 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7158 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7156 |
| Histone deacetylase 8 | Q9BY41 | HDAC8_HUMAN | Homo sapiens | 3 | 0.7156 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7139 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7139 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7131 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7131 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 3 | 0.7129 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7129 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 3 | 0.7129 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7129 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7128 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7128 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7127 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7127 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7123 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7123 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7114 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7114 |
| Histone-lysine N-methyltransferase 2C | Q8NEZ4 | KMT2C_HUMAN | Homo sapiens | 3 | 0.7114 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7114 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7097 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7097 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7095 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7095 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7091 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7091 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7090 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7090 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 3 | 0.7088 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 3 | 0.7088 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7079 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7079 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7079 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7079 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7072 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7072 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7067 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7067 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7066 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7066 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 3 | 0.7057 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 3 | 0.7057 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7055 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7055 |
| Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 2 | 0.7047 |
| Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 2 | 0.7047 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7046 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7046 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7044 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7044 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7043 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7043 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7043 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7043 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7041 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7041 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7036 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7036 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7030 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7030 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7024 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7024 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7022 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7022 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7020 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7020 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7018 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7018 |
| Acetylglutamate kinase | Q0ASS9 | Q0ASS9_MARMM | Maricaulis maris | 3 | 0.7015 |
| Acetylglutamate kinase | Q0ASS9 | Q0ASS9_MARMM | Maricaulis maris | 3 | 0.7015 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7013 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7013 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7011 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7011 |
| Basic phospholipase A2 homolog piratoxin-1 | P58399 | PA2H1_BOTPI | Bothrops pirajai | 4 | 0.7006 |
| Basic phospholipase A2 homolog piratoxin-1 | P58399 | PA2H1_BOTPI | Bothrops pirajai | 4 | 0.7006 |