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Laricitrin

Family: Plantae - Myrtaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1cc(cc(c1O)O)c1oc2cc(O)cc(c2c(=O)c1O)O
InChI	InChI=1S/C16H12O8/c1-23-11-3-6(2-9(19)13(11)20)16-15(22)14(21)12-8(18)4-7(17)5-10(12)24-16/h2-5,17-20,22H,1H3
InChIKey	CFYMYCCYMJIYAB-UHFFFAOYSA-N
Formula	C₁₆H₁₂O₈
HBA	8
HBD	5
MW	332.26
Rotatable Bonds	2
TPSA	140.59
LogP	2.0
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.06
Exact Mass	332.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Syzygium cumini	Myrtaceae	Plantae	—

Showing of synonyms

Eldin Elhawary S.S, Elmotyam A.K.E, et al. (2022). Cytotoxic and anti-diabetic potential, metabolic profiling and insilico studies of Syzygium cumini (L.) Skeels belonging to family Myrtaceae. Natural product research,2022, 36(4), 1026-1030. [View] [PubMed]

Pubchem: 5282154

Cas: 53472-37-0

Zinc: ZINC000006483599

Kegg Ligand: C12633

Chebi: 31763

Nmrshiftdb2: 60022467

Metabolights: MTBLC31763

Chembl: CHEMBL2260151

Comptox: DTXSID40415210

CPRiL: 166158

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

Level: 1

Mol. Weight: 332.26 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 332.26 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 332.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.3
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.410
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.950
Plasma Protein Binding: 91.82
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.160
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.750
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.120
Micronucleos: Toxic
NR-AhR: Toxic
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: 3.100
Rat (Acute): 2.450
Rat (Chronic Oral): 3.570
Fathead Minnow: 3.840
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 523.760
Hydration Free Energy: -11.060
Log(D) at pH=7.4: 1.350
Log(P): 1.01
Log S: -4.36
Log(Vapor Pressure): -7.5
Melting Point: 273.02
pKa Acid: 4.92
pKa Basic: 5.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9097
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9047
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8980
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8977
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8976
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8970
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8960
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8905
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8904
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8900
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8869
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8837
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8835
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8829
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8815
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8803
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.8760
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.8756
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8752
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.8741
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8737
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8719
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8706
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8625
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8603
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.8590
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8578
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8534
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.8521
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8511
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8500
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8488
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8485
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8484
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8472
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8471
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8457
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.8455
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8432
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8385
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8375
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8339
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8334
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8312
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.8305
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8293
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8283
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8262
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8251
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8245
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8243
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	5	0.8177
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8176
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8172
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8138
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8097
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8095
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.8086
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8073
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8070
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8067
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8061
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8060
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8052
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	6	0.8048
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8047
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8030
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8013
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.8011
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8005
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	5	0.7977
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7971
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7924
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7908
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7857
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7844
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	5	0.7836
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	6	0.7825
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7825
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7815
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7804
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7797
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7792
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7775
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7775
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7758
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7753
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7747
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7746
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7733
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7730
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7721
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7687
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7666
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7663
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7642
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7631
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7631
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7629
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7627
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7627
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7614
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7609
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7604
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7603
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7584
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7573
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7571
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7563
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	4	0.7557
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7556
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7555
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7546
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	7	0.7544
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7541
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7539
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7530
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7528
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7514
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7512
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7507
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7506
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7502
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7489
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7488
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7487
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7486
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7483
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7481
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7470
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7468
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7461
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7447
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7441
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	5	0.7440
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7433
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7432
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7428
Cyclin-dependent kinase 6	Q00534	CDK6_HUMAN	Homo sapiens	5	0.7413
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7412
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7412
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	5	0.7382
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7377
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7365
Glycosyltransferase	A4F1R4	A4F1R4_CLITE	Clitoria ternatea	5	0.7346
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7338
Quercetin 2,3-dioxygenase	Q7SIC2	QDOI_ASPJA	Aspergillus japonicus	4	0.7337
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7314
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7314
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7308
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7306
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7301
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7282
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7277
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7274
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7271
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7265
Heat shock protein 75 kDa, mitochondrial	Q12931	TRAP1_HUMAN	Homo sapiens	4	0.7235
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7226
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7206
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7204
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7201
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7194
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7189
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7189
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7187
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7187
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.7167
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7156
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7152
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7150
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7150
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7140
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7139
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7136
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7132
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7132
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7123
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7116
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7110
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7109
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7107
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7104
Replicase polyprotein 1ab	P0C6X7	R1AB_CVHSA	Human SARS coronavirus	4	0.7098
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7098
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7081
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7078
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7074
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7074
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7065
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7062
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7061
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7049
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	3	0.7048
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7048
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7045
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7041
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7038
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	5	0.7021
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7018
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	3	0.7013
Protein kinase, putative	Q4YRR5	Q4YRR5_PLABA	Plasmodium berghei	4	0.7003

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