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Phillygenin

Family: Scrophulariaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1OC)[C@@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1ccc(c(c1)OC)O
InChI	InChI=1S/C21H24O6/c1-23-17-7-5-13(9-19(17)25-3)21-15-11-26-20(14(15)10-27-21)12-4-6-16(22)18(8-12)24-2/h4-9,14-15,20-22H,10-11H2,1-3H3/t14-,15-,20+,21-/m0/s1
InChIKey	CPJKKWDCUOOTEW-YJPXFSGGSA-N
Formula	C₂₁H₂₄O₆
HBA	6
HBD	1
MW	372.42
Rotatable Bonds	5
TPSA	66.38
LogP	3.49
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.43
Exact Mass	372.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eremophila maculata	Scrophulariaceae	Plantae	1214565

Showing of synonyms

Youssef F.S, Ashour M.L, et al. (2016). Eremophila maculata —Isolation of a rare naturally-occurring lignan glycoside and the hepatoprotective activity of the leaf extract. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2016, 23(12), 1484-1493. [View] [PubMed]

Pubchem: 3083590

Cas: 487-39-8

Zinc: ZINC000005037520

Nmrshiftdb2: 70128096

Chembl: CHEMBL2260010

Comptox: DTXSID80197588

CPRiL: 58115

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 266.34 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 190.24 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 114.14 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.680
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.130
Plasma Protein Binding: 78.14
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.890
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.990
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.630
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.780
Micronucleos: Safe
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: Toxic
T. Pyriformis: -11.610
Rat (Acute): 2.180
Rat (Chronic Oral): 2.140
Fathead Minnow: 4.230
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 436.210
Hydration Free Energy: -5.810
Log(D) at pH=7.4: 2.800
Log(P): 2.35
Log S: -4.32
Log(Vapor Pressure): -7.94
Melting Point: 156.32
pKa Acid: 9.03
pKa Basic: 4.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9696
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9561
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9437
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9332
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9205
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9202
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.9180
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9135
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9121
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9103
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9089
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9066
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9028
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8904
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8867
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8844
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8805
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8720
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8665
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8649
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8588
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8370
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8359
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8354
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8290
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8248
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8245
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8230
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8219
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	4	0.8128
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8124
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8121
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8101
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8096
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8069
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.8042
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.8030
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8003
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7993
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7974
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7962
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7933
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.7922
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7909
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7887
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7849
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7836
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7731
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7728
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7683
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7665
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7627
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7625
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7580
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7574
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7567
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7565
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7564
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7557
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7556
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7553
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7547
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7545
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7533
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7525
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7500
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7494
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7476
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7474
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7471
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7449
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7447
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7444
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7444
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7440
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7430
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7422
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7421
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7411
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7406
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7404
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7395
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7392
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7377
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7371
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7370
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7367
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7366
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7361
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7360
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7354
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7347
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7322
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7320
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7315
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7312
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7306
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7286
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7285
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7284
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7279
ATP-dependent protease subunit HslV	P0A7B8	HSLV_ECOLI	Escherichia coli	3	0.7276
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7274
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7273
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7266
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7261
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7259
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7256
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7254
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7245
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7242
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	2	0.7232
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7228
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7222
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7217
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7213
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7212
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7203
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7201
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7185
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7174
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7173
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	2	0.7171
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7170
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7168
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7167
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7158
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	4	0.7158
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7150
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7142
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7140
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7138
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7137
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7136
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7129
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7127
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7126
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7122
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7122
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7117
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7117
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7113
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7113
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	3	0.7112
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7111
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7110
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7110
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7107
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7107
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7106
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7106
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7106
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7100
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7100
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7098
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7095
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7082
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	3	0.7081
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7071
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7069
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7066
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7064
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7060
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7060
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7056
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7055
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7053
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7048
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7037
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7033
RAC-alpha serine/threonine-protein kinase	P31749	AKT1_HUMAN	Homo sapiens	4	0.7025
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7025
Renin	P00797	RENI_HUMAN	Homo sapiens	4	0.7018
Transitional endoplasmic reticulum ATPase	P55072	TERA_HUMAN	Homo sapiens	3	0.7004
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7002

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