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Canniflavone

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylated Flavone

Canonical Smiles	COc1cc(ccc1O)c1cc(=O)c2c(o1)cc(c(c2O)CC=C(C)C)O
InChI	InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-19-20(21(13)25)16(24)10-17(27-19)12-5-7-14(22)18(8-12)26-3/h4-5,7-10,22-23,25H,6H2,1-3H3
InChIKey	IXCUTZUASDSIJO-UHFFFAOYSA-N
Formula	C₂₁H₂₀O₆
HBA	6
HBD	3
MW	368.39
Rotatable Bonds	4
TPSA	100.13
LogP	4.09
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	368.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia ciliata	Moraceae	Plantae	2604984
2	Dorstenia mannii	Moraceae	Plantae	194258

Showing of synonyms

Ngadjui BT, Ngameni B, et al. (2002). Prenylated and geranylated chalcones and flavones from the aerial parts of Dorstenia ciliata. Bulletin of The Chemical Society of Ethiopia, 2002, 16(2), 157-164. [View]
Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]

Pubchem: 403815

Cas: 76735-58-5

Nmrshiftdb2: 70008200

Chembl: CHEMBL1985794

CPRiL: 107711

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 368.39 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 368.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.99
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.930
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.300
Plasma Protein Binding: 89.86
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.590
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.520
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.170
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.500
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -0.610
Rat (Acute): 2.250
Rat (Chronic Oral): 2.890
Fathead Minnow: 5.100
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 489.910
Hydration Free Energy: -10.490
Log(D) at pH=7.4: 3.660
Log(P): 4.9
Log S: -6.7
Log(Vapor Pressure): -8.42
Melting Point: 208.82
pKa Acid: 7.75
pKa Basic: 6.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9813
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9751
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9634
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9588
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9407
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9403
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9390
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9298
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9245
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9176
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9166
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.9125
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9117
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9113
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9090
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.9088
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.9004
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8811
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8796
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8794
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8734
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8686
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8668
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8614
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8603
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8601
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8568
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8563
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8554
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8540
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8506
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8495
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8490
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8456
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8435
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8379
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8373
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8306
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8292
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8263
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8263
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8255
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8249
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8247
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8242
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8235
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8205
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8190
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8151
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8130
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8122
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8096
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.8085
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.8070
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.8042
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8037
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8008
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8006
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7977
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7957
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.7951
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7925
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7923
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7922
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7920
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7908
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7893
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7866
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7828
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7793
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7788
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7761
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7759
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7756
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7752
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7690
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7683
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7679
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7671
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7655
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7644
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7639
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7633
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7631
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7618
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7616
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7586
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7581
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7576
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7574
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7572
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7561
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7560
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7550
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7549
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7546
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7544
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7540
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7538
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7534
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7534
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7531
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7527
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7522
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7517
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7512
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7510
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7504
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7500
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7493
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7486
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7484
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7478
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7475
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7472
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7457
Thymidylate kinase	Q9HZN8	KTHY_PSEAE	Pseudomonas aeruginosa	3	0.7456
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7452
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7449
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7445
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7431
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7418
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7417
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7413
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7398
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7383
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7375
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7372
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7363
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7355
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7349
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7341
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7334
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7327
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7317
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7300
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7299
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7296
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7296
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7286
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7283
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7278
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7275
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7273
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7271
DNA-(apurinic or apyrimidinic site) lyase	Q97FM4	Q97FM4_CLOAB	Clostridium acetobutylicum	4	0.7262
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7260
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7255
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7253
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7249
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7246
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.7230
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7219
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7214
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7210
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7205
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7204
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7201
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7191
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7187
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7186
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7176
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7176
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7170
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7169
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7168
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7165
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7164
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7151
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7148
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7137
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7130
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7129
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7124
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7123
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7123
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7121
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7110
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7095
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7086
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7077
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7075
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7074
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.7065
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7065
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7060
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7055
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7035
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7031
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7026
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7026
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7024
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7021
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7005

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