Marmin - Compound Card

Marmin

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Marmin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles C/C(=C\COc1ccc2c(c1)oc(=O)cc2)/CC[C@H](C(O)(C)C)O
InChI InChI=1S/C19H24O5/c1-13(4-8-17(20)19(2,3)22)10-11-23-15-7-5-14-6-9-18(21)24-16(14)12-15/h5-7,9-10,12,17,20,22H,4,8,11H2,1-3H3/b13-10+/t17-/m1/s1
InChIKey QYYKWTUUCOTGNS-JIIJFUIFSA-N
Formula C19H24O5
HBA 5
HBD 2
MW 332.4
Rotatable Bonds 7
TPSA 79.9
LogP 3.03
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 332.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pituranthos triradiatus Apiaceae Plantae 99500
2 Deverra battandieri Apiaceae Plantae 1589787

Showing of synonyms

  • Esseid C, León F, et al. (2021). Coumarins and other constituents from Deverra battandieri. Phytochemistry Letters, 2021, 42, 129-133.. [View]
  • Halim AF, Lahioub MF, et al. (1989). Coumarins of Pituranthos triradiatus Growing in Egypt. Planta Medica,1989,55,609. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 332.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.3
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.03
Plasma Protein Binding
65.1
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.58
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.31
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.47
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.6
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
0.84
Rat (Acute)
2.38
Rat (Chronic Oral)
1.97
Fathead Minnow
4.74
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
412.62
Hydration Free Energy
-13.08
Log(D) at pH=7.4
2.4
Log(P)
2.48
Log S
-3.92
Log(Vapor Pressure)
-7.54
Melting Point
139.21
pKa Acid
7.81
pKa Basic
6.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9856
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9856
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9754
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9754
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9735
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9735
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9719
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9719
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9553
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9553
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9546
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9546
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9510
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9510
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9491
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9491
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9475
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9475
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9216
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9216
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9097
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9097
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9001
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9001
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8905
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8905
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8893
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8893
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8834
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8834
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8826
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8826
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8763
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8763
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8722
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8722
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8715
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8715
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8695
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8695
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8572
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8572
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8438
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8438
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8429
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8429
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.8428
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.8428
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8296
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8296
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 4 0.8291
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 4 0.8291
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.8253
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.8253
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8251
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8251
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.8237
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.8237
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8233
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8233
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8213
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8213
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8141
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8141
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8136
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8136
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8121
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8121
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8104
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.8104
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.8088
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.8088
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8069
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8069
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8050
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8050
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8016
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8016
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8013
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8013
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7976
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7976
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7956
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7956
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7943
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7943
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7911
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7911
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7908
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7908
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7903
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7903
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7875
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7875
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7871
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7871
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7863
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7863
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7862
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7862
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7830
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7830
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7811
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7811
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7804
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7804
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7793
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7793
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7781
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7781
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7764
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7764
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7763
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 4 0.7763
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7760
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7760
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7750
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7750
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7742
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7742
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7737
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7737
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7732
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7732
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7726
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7726
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7721
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7721
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7720
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7720
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7720
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7720
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7682
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7682
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7681
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7681
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7656
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7656
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7653
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7653
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7628
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7628
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7628
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7628
Cytochrome b6 P83791 CYB6_MASLA Mastigocladus laminosus 3 0.7606
Cytochrome b6 P83791 CYB6_MASLA Mastigocladus laminosus 3 0.7606
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7600
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7600
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7594
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7594
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7592
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7592
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7589
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7589
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7588
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7588
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7584
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7584
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7584
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7584
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7581
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7581
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7570
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7570
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7568
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7568
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7554
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7554
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7553
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7553
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7550
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7550
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7544
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7544
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7541
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7541
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7514
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7514
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7512
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7512
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7502
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7502
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7498
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7498
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7496
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7496
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7479
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7479
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7458
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7458
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7455
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7455
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7453
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7453
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7452
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7452
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7442
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7442
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7437
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7437
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7430
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7430
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7427
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7427
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7414
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7414
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7410
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7410
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7405
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7405
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7402
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7402
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7394
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7394
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7387
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7387
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7382
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7382
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7379
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7379
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7372
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7372
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7359
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7359
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7357
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7357
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7348
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7348
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7344
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7344
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7333
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7333
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7326
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7326
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7320
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7320
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7307
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7307
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7307
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7307
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7304
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7304
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7304
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7304
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7301
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7301
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7290
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7290
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7276
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7276
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7272
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7272
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7268
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7268
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7262
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7262
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7259
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7259
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7246
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7246
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7238
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7238
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7233
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7233
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7231
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7231
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7230
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7230
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7225
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7225
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7218
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7218
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7213
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7213
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7209
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7209
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7206
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7206
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7201
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7201
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7200
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7200
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7199
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7199
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7195
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7195
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7195
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7195
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7192
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7192
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7190
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7190
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7179
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7179
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7178
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7178
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7178
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7178
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7173
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7173
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7172
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7172
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7172
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7172
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7166
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7166
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7163
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7163
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7159
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7159
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7156
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7156
Alpha-tocopherol transfer protein Q8BWP5 TTPA_MOUSE Mus musculus 4 0.7137
Alpha-tocopherol transfer protein Q8BWP5 TTPA_MOUSE Mus musculus 4 0.7137
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7133
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7133
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7113
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7113
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7113
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7113
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7101
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7101
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7100
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7100
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7098
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7098
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7097
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7097
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7090
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7090
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7088
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7088
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7084
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7084
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7068
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7068
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7062
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7062
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7054
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7054
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7053
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7053
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7051
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7044
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7044
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7022
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7022
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7010
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7010
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7001
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7001

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