1,5-dicaffeoylquinic acid - Compound Card

1,5-dicaffeoylquinic acid

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1,5-dicaffeoylquinic acid

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles O=C(O[C@H]1C[C@@](OC(=O)/C=C/c2ccc(c(c2)O)O)(C[C@@H]([C@H]1O)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(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3-,8-4+/t19-,20-,23+,25-/m0/s1
InChIKey YDDUMTOHNYZQPO-CZWHYVATSA-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 Echinops galalensis Asteraceae-Compositae Plantae 32194

Showing of synonyms

  • Abdallah HM, Ezzat SM, et al. (2013). Protective effect of Echinops galalensis against CCl4-induced injury on the human hepatoma cell line (Huh7). Phytochemistry Letters,2013,6,73-78. [View]
Pubchem: 24720973
Nmrshiftdb2: 70000285
CPRiL: 20198
Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(CCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 376.45 g/mol

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 230.31 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 84.16 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Protective against ccl4-induced injury on the human hepatoma cell line (huh7)

Absorption

Caco-2 (logPapp)
-6.78
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.13
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
90.13
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
9.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.84
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.02
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
-471.35
Rat (Acute)
2.18
Rat (Chronic Oral)
3.5
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
579.61
Hydration Free Energy
-3.07
Log(D) at pH=7.4
0.15
Log(P)
1.35
Log S
-2.66
Log(Vapor Pressure)
-14.69
Melting Point
216.79
pKa Acid
5.29
pKa Basic
5.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9150
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9150
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.9149
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.9149
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9120
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9120
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9099
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9099
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8891
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8891
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8785
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8785
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8762
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.8762
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8712
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8712
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8690
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8690
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8552
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.8552
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8487
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8487
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8444
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8444
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8351
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8351
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8338
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8338
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8296
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8296
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8241
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8241
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8136
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8136
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8093
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8093
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8010
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8010
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 3 0.7995
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 3 0.7995
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7966
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7966
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7962
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7962
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7931
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7931
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7930
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7930
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.7928
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.7928
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7906
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7906
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7899
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7899
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7883
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7883
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7805
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7805
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7805
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7805
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7785
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7785
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7750
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7750
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7723
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7723
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.7677
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.7677
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7646
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7646
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7646
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7646
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7642
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7642
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7640
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7640
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7613
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7613
Probable enoyl-CoA hydratase EchA8 P9WNN9 ECHA8_MYCTU Mycobacterium tuberculosis 4 0.7611
Probable enoyl-CoA hydratase EchA8 P9WNN9 ECHA8_MYCTU Mycobacterium tuberculosis 4 0.7611
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7596
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7596
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7585
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7585
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7581
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7581
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7579
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7579
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7544
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7544
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7495
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7495
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7452
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7452
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7424
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7424
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7418
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7418
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7400
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 3 0.7400
Type 2 DNA topoisomerase 6 subunit B O05207 TOP6B_SACSH Saccharolobus shibatae 3 0.7393
Type 2 DNA topoisomerase 6 subunit B O05207 TOP6B_SACSH Saccharolobus shibatae 3 0.7393
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7382
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7382
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7381
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7381
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7378
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7378
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7377
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7377
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7377
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7377
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7356
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7356
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7349
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7349
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7321
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7321
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7312
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7312
Poly(A) polymerase, putative Q381M1 Q381M1_TRYB2 Trypanosoma brucei brucei 4 0.7307
Poly(A) polymerase, putative Q381M1 Q381M1_TRYB2 Trypanosoma brucei brucei 4 0.7307
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7289
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7289
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7281
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7281
Probable enoyl-CoA hydratase EchA8 P9WNN9 ECHA8_MYCTU Mycobacterium tuberculosis 3 0.7278
Probable enoyl-CoA hydratase EchA8 P9WNN9 ECHA8_MYCTU Mycobacterium tuberculosis 3 0.7278
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7266
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7266
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7264
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7264
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 3 0.7256
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 3 0.7256
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7231
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7231
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7226
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7226
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7225
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7225
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7202
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7202
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7161
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7161
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7160
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7160
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7142
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7142
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7138
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7138
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7133
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7133
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7131
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7131
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7129
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7118
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7118
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7116
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7116
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7109
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7107
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7107
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7100
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7100
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7076
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7076
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7073
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7073
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7072
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7072
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7057
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7057
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7052
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7052
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Eukaryotic translation initiation factor 4E type 2 O60573 IF4E2_HUMAN Homo sapiens 4 0.7045
Eukaryotic translation initiation factor 4E type 2 O60573 IF4E2_HUMAN Homo sapiens 4 0.7045
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7044
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7044
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7042
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7042
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7040
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7040
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7040
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7040
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7040
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7035
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7035
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7035
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7032
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7032
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7020
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7020
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7017
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7017
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7007
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7007
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7004
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7004

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