Caffeic anhydride - Compound Card

Caffeic anhydride

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Caffeic anhydride

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Diarylheptanoid
Canonical Smiles O=C(OC(=O)C=Cc1ccc(c(c1)O)O)C=Cc1ccc(c(c1)O)O
InChI InChI=1S/C18H14O7/c19-13-5-1-11(9-15(13)21)3-7-17(23)25-18(24)8-4-12-2-6-14(20)16(22)10-12/h1-10,19-22H
InChIKey QDPOOGQUCJJZAO-UHFFFAOYSA-N
Formula C18H14O7
HBA 7
HBD 4
MW 342.3
Rotatable Bonds 4
TPSA 124.29
LogP 2.31
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 342.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae-Compositae Plantae 119186

Showing of synonyms

  • Abdel Bar F.M, Elsbaey M, et al. (2020). Phytochemical, antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1b,2a,3b,19a,23-pentahydroxy-urs-12-en-28-oic acid. Natural product research, 2020, 34(6), 804-809. [View] [PubMed]
Pubchem: 57096377

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 278.31 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.34
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
29.09
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.260
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.280
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.710
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.130
Rat (Acute)
2.170
Rat (Chronic Oral)
3.250
Fathead Minnow
4.390
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
501.970
Hydration Free Energy
-11.430
Log(D) at pH=7.4
1.880
Log(P)
2.53
Log S
-3.39
Log(Vapor Pressure)
-9.41
Melting Point
233.51
pKa Acid
6.86
pKa Basic
5.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9780
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.9678
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9527
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.9507
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9351
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.9272
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9176
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.9161
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9152
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9140
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9134
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9122
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9110
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.9023
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9015
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8970
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 4 0.8961
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8934
Heat shock cognate 90 kDa protein P54651 HSC90_DICDI Dictyostelium discoideum 3 0.8930
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8925
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8904
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8885
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.8854
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8835
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8827
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8761
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8731
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8717
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8699
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8679
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8665
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8634
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8633
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8632
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8629
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8627
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8625
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8618
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8607
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8569
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8567
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8565
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.8549
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.8481
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8470
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.8465
Xanthine dehydrogenase/oxidase P22985 XDH_RAT Rattus norvegicus 3 0.8458
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8443
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.8438
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8411
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8402
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.8388
Bifunctional hemolysin/adenylate cyclase P0DKX7 CYAA_BORPE Bordetella pertussis 3 0.8375
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.8367
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.8360
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8358
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8342
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8332
Catechol O-methyltransferase P21964 COMT_HUMAN Homo sapiens 3 0.8322
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8320
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 3 0.8317
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8310
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8298
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8292
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8287
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8286
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8286
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8284
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.8273
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8268
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8263
Monomeric sarcosine oxidase P40859 MSOX_BACB0 Bacillus sp 3 0.8241
Bifunctional protein GlmU P43889 GLMU_HAEIN Haemophilus influenzae 3 0.8223
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8219
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8178
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8173
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8171
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.8166
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8159
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8148
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8145
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8141
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8138
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8125
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8124
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8114
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.8109
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8097
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8093
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8093
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8063
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8053
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8040
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8040
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.8017
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8002
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7998
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7984
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7975
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7974
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7965
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 4 0.7940
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7939
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7935
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7923
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7917
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.7912
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7912
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7912
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7901
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7889
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7880
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7877
Isochorismate pyruvate lyase Q51507 PCHB_PSEAE Pseudomonas aeruginosa 2 0.7872
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7858
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7855
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7834
M17 leucyl aminopeptidase Q8IL11 Q8IL11_PLAF7 Plasmodium falciparum 3 0.7833
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7817
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7806
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7801
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7798
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7784
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7780
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7770
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.7767
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7765
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7752
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7748
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7740
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7727
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7725
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7715
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7706
tRNA (cytidine-2'-O-)-methyltransferase TrmJ Q4JB16 TRMJ_SULAC Sulfolobus acidocaldarius 4 0.7694
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7690
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7687
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7686
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7683
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7678
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7675
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7672
Pol protein Q000H7 Q000H7_9HIV1 Human immunodeficiency virus 1 3 0.7671
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7656
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7655
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7624
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7614
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7610
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7604
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7597
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7595
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7579
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 4 0.7578
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7571
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7565
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7555
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7553
Arginine kinase O15992 KARG_ANTJA Anthopleura japonica 3 0.7540
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7536
Orotidine 5'-phosphate decarboxylase Q5L0U0 PYRF_GEOKA Geobacillus kaustophilus 3 0.7533
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7528
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7522
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.7519
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7514
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7513
Nucleoside diphosphate kinase O58429 NDK_PYRHO Pyrococcus horikoshii 3 0.7513
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7507
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7498
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7496
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7493
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7490
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7487
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7484
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7481
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7479
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7465
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7465
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7464
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7463
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 3 0.7459
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7457
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7454
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7443
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7442
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7442
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7440
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7429
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7429
Gag-Pol polyprotein P04587 POL_HV1B5 Human immunodeficiency virus type 1 group M subtype B 3 0.7419
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7419
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7411
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7410
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7407
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7406
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7400
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7400
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7397
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7397
Mevalonate kinase P17256 KIME_RAT Rattus norvegicus 3 0.7392
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7384
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7376
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7369
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7368
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7364
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7364
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7361
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7360
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7352
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7341
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7340
Spermidine synthase Q8II73 Q8II73_PLAF7 Plasmodium falciparum 4 0.7338
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7337
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7332
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7330
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7329
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7328
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7327
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7326
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7326
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7317
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7308
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7302
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7300
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7297
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7288
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7285
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7281
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7280
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7280
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7279
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7276
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7272
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7272
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7271
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 5 0.7265
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7263
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7261
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.7252
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7251
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7250
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7249
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 4 0.7245
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7238
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7234
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7232
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7231
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7226
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7226
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7225
Flavonoid 3-O-glucosyltransferase A6XNC6 UGFGT_MEDTR Medicago truncatula 3 0.7223
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7221
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7221
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7219
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7214
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7212
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7209
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 3 0.7208
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7207
Phosphoglycerate kinase Q83AU6 PGK_COXBU Coxiella burnetii 3 0.7203
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7201
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7198
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7197
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7192
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7188
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7180
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7177
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7175
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7175
eIF-2-alpha kinase GCN2 P15442 GCN2_YEAST Saccharomyces cerevisiae 3 0.7174
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7161
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7158
Mitochondrial dynamics protein MIEF1 Q9NQG6 MID51_HUMAN Homo sapiens 3 0.7156
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7154
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7152
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7146
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7146
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7143
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.7142
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7140
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7139
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7138
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7138
Aspartate-semialdehyde dehydrogenase Q51344 DHAS_PSEAE Pseudomonas aeruginosa 3 0.7133
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7126
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7124
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7123
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7123
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7121
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7118
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7118
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7115
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7114
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7114
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7111
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7110
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7110
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7110
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 2 0.7109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7108
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7105
Protein-tyrosine kinase 2-beta Q14289 FAK2_HUMAN Homo sapiens 3 0.7104
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7101
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7098
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7096
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7096
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7095
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 3 0.7095
Purine nucleoside phosphorylase 2 P45563 XAPA_ECOLI Escherichia coli 3 0.7094
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 3 0.7094
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7091
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7091
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7090
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.7089
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7088
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7088
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7087
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7085
Salicylate synthase P9WFX1 MBTI_MYCTU Mycobacterium tuberculosis 3 0.7082
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7081
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7081
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7080
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7078
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7076
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7074
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7071
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7070
tRNA (guanine-N(1)-)-methyltransferase Q2GIL5 TRMD_ANAPZ Anaplasma phagocytophilum 3 0.7069
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7066
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7066
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7065
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7065
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7062
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7062
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7061
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7059
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7059
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7057
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7054
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7054
Mannosylglycerate synthase D0MI02 D0MI02_RHOM4 Rhodothermus marinus 3 0.7053
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7052
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7046
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7045
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7041
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7040
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7038
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7034
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7034
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7033
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7032
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7032
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7030
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7025
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 2 0.7024
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7023
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7020
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7020
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7017
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7015
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7014
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7014
Eukaryotic translation initiation factor 4E type 2 O60573 IF4E2_HUMAN Homo sapiens 4 0.7011
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 4 0.7009
Nitrogen regulatory protein P-II O66513 GLNB_AQUAE Aquifex aeolicus 2 0.7008
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7005
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7005
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7002
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7002
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7000

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