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L-chicoric acid
- Family: Plantae - Euphorbiaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | O=C(O[C@H]([C@H](C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1 |
| InChIKey | YDDGKXBLOXEEMN-IABMMNSOSA-N |
| Formula | C22H18O12 |
| HBA | 10 |
| HBD | 6 |
| MW | 474.37 |
| Rotatable Bonds | 9 |
| TPSA | 208.12 |
| LogP | 1.23 |
| Number Rings | 2 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.09 |
| Exact Mass | 474.08 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Alchornea cordifolia | Euphorbiaceae | Plantae | 316697 |
Showing of synonyms
L-chicoric acid
Chicoric acid
Cichoric Acid
70831-56-0
6537-80-0
(-)-Chicoric acid
Dicaffeoyltartaric acid
(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
(-)-L-Chicoric acid
NSC 699173
Chicoric acid, (-)-
S4YY3V8YHD
Trans-Caffeoyltartaric acid
NSC-699173
2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
(R-(R*,R*-(E,E)))-2,3-Bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
CHICORIC ACID [USP-RS]
NSC-99173
Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (2R,3R)-
Butanedioic acid, 2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*-(E,E)))-
TARTARIC ACID, BIS(3,4-DIHYDROXYCINNAMATE)
CHICORIC ACID (USP-RS)
Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))-
Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2R,3R)-
(2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid
(2S,3S)-2,3-bis((((2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy))butanedioic acid
(2S,3S)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
(2R,3R)-2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic acid
636-229-3
CHICORIC ACID (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS)
(2s,3s)-2,3-bis(((e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)butanedioic acid
(2s,3s)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
L-Cichoric acid
L-DCTA
NSC699173
Dicaffeoyl-L-tartaric acid
CHEBI:3594
CHEMBL282731
DTXSID0033332
(2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
(2R,3R)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid
(2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)-
UNII-S4YY3V8YHD
L-Chicoricacid
1-chicoricacid
Cichoric-Acid
L-Chicoric-acid
GKP
L-CA
(-)-CICHORIC ACID
2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
DTXCID8013332
SCHEMBL15532218
2,3-Dicaffeoyl-L-tartaric acid
YDDGKXBLOXEEMN-IABMMNSOSA-N
GLXC-10979
Chicoric Acid, >=95% (HPLC)
HY-N0457
MSK40121
Tox21_201055
BDBM50076273
MFCD00189418
MSK181147
S9133
AKOS000278435
CCG-269487
CS-4262
FC65730
( -)-Chicoric acid, analytical standard
NCGC00091914-01
NCGC00091914-02
NCGC00091914-04
NCGC00258608-01
1ST40121
AC-34315
AC-36990
AS-56447
DA-72145
DA-72146
CAS-70831-56-0
C3450
NS00037116
D78144
Q5119402
Chicoric Acid, United States Pharmacopeia (USP) Reference Standard
(2R,3R)-2,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
(2R,3R)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic acid
(2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}succinic acid
(2R,3R)-2,3-bis{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
[S-(R*,R*)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid
Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)- (9CI)
Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R-[R*,R*-(E,E)]]-
NCGC00091914-04!(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
Pubchem:
5281764
Cas:
70831-56-0
Gnps:
CCMSLIB00006435440
Zinc:
ZINC000004098726
Kegg Ligand:
C10437
Chebi:
3594
Nmrshiftdb2:
60033669
Chembl:
CHEMBL282731
Comptox:
DTXSID0033332
Pdb Ligand:
GKP
Bindingdb:
50076273
CPRiL:
63614
SMILES: c1ccccc1C=CC(=O)OCCOC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 474.37 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 474.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.34
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.460
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -5.6
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.680
- Plasma Protein Binding
- 67.64
- 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
- Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-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
- 6.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.530
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.610
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.940
- 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
- -81.200
- Rat (Acute)
- 1.970
- Rat (Chronic Oral)
- 3.530
- Fathead Minnow
- 3.960
- 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
- 622.190
- Hydration Free Energy
- -3.870
- Log(D) at pH=7.4
- -1.590
- Log(P)
- 2.05
- Log S
- -2.48
- Log(Vapor Pressure)
- -16.95
- Melting Point
- 264.0
- pKa Acid
- 5.83
- pKa Basic
- 3.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 3 | 0.9442 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9343 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9300 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9113 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9088 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.8954 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8950 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 3 | 0.8943 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8901 |
| MutT/nudix family protein | Q5SJY9 | Q5SJY9_THET8 | Thermus thermophilus | 3 | 0.8857 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 3 | 0.8757 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8739 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8684 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8622 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8606 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8529 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8495 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8441 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8396 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 3 | 0.8389 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.8369 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8346 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8315 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.8224 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.8214 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.8169 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8167 |
| Caffeic acid 3-O-methyltransferase | P28002 | COMT1_MEDSA | Medicago sativa | 3 | 0.8127 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8046 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8027 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8017 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 3 | 0.8008 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8005 |
| Adenosylmethionine-8-amino-7-oxononanoate aminotransferase | P12995 | BIOA_ECOLI | Escherichia coli | 3 | 0.7981 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 4 | 0.7972 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7947 |
| Non-receptor tyrosine-protein kinase TYK2 | P29597 | TYK2_HUMAN | Homo sapiens | 3 | 0.7906 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7879 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7855 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7854 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7802 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7788 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7788 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7752 |
| 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase | B1MKD5 | B1MKD5_MYCA9 | Mycobacteroides abscessus | 3 | 0.7742 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7741 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7688 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7688 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7687 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7680 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7667 |
| Glutathione S-transferase F2 | P46422 | GSTF2_ARATH | Arabidopsis thaliana | 3 | 0.7600 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7594 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7581 |
| Nucleoside diphosphate kinase | A5J299 | A5J299_PENVA | Penaeus vannamei | 3 | 0.7548 |
| Glucose-1-phosphate adenylyltransferase small subunit, chloroplastic/amyloplastic | P23509 | GLGS_SOLTU | Solanum tuberosum | 3 | 0.7546 |
| non-specific serine/threonine protein kinase | Q6FS46 | Q6FS46_CANGA | Candida glabrata | 4 | 0.7516 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7504 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7495 |
| 5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase | Q8U0R7 | PURP_PYRFU | Pyrococcus furiosus | 3 | 0.7476 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7462 |
| Amino-acid acetyltransferase | Q5FAK7 | Q5FAK7_NEIG1 | Neisseria gonorrhoeae | 3 | 0.7461 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 4 | 0.7456 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7450 |
| Thymidylate synthase | P04818 | TYSY_HUMAN | Homo sapiens | 4 | 0.7430 |
| SRSF protein kinase 1 | Q96SB4 | SRPK1_HUMAN | Homo sapiens | 4 | 0.7419 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7374 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7367 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7364 |
| Nucleoside diphosphate kinase | O58429 | NDK_PYRHO | Pyrococcus horikoshii | 3 | 0.7362 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7360 |
| mRNA-capping enzyme subunit alpha | P78587 | MCE1_CANAX | Candida albicans | 3 | 0.7320 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7312 |
| Ectonucleoside triphosphate diphosphohydrolase I | Q5ZUA2 | Q5ZUA2_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.7310 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7301 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 3 | 0.7293 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7288 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7285 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7279 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7279 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7278 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7275 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 4 | 0.7264 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7262 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7253 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 2 | 0.7252 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7246 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7246 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7245 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7240 |
| MutT/nudix family protein | O33199 | O33199_MYCTO | Mycobacterium tuberculosis | 3 | 0.7238 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7237 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7237 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7236 |
| Thymidylate synthase | P0A886 | TYSY_ECO57 | Escherichia coli O157:H7 | 3 | 0.7236 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7235 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7229 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7221 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7205 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7202 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.7202 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7201 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7196 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7194 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7189 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7188 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7181 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7176 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7175 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7174 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7168 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.7168 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7160 |
| Eukaryotic translation initiation factor 2 subunit alpha | P20459 | IF2A_YEAST | Saccharomyces cerevisiae | 3 | 0.7158 |
| Bifunctional AAC/APH | P0A0C1 | AACA_STAAU | Staphylococcus aureus | 4 | 0.7155 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 4 | 0.7150 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7149 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7145 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7141 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7138 |
| Malate dehydrogenase | P10584 | MDH_THETH | Thermus thermophilus | 3 | 0.7131 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7129 |
| Glycerol kinase | P0A6F3 | GLPK_ECOLI | Escherichia coli | 4 | 0.7127 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7127 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7127 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7127 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7126 |
| Uncharacterized protein | Q8DY32 | Q8DY32_STRA5 | Streptococcus agalactiae serotype V | 4 | 0.7116 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7115 |
| Adenylosuccinate synthetase | P0A7D4 | PURA_ECOLI | Escherichia coli | 4 | 0.7113 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7113 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7111 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 2 | 0.7103 |
| Formate--tetrahydrofolate ligase | Q2RM91 | FTHS_MOOTA | Moorella thermoacetica | 2 | 0.7101 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7099 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7098 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7093 |
| Eukaryotic translation initiation factor 4E type 2 | O60573 | IF4E2_HUMAN | Homo sapiens | 4 | 0.7080 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7080 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7077 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7074 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7073 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7065 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7065 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7063 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7063 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7062 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7056 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7050 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7044 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7041 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 4 | 0.7036 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7025 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7024 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7023 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7008 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7006 |