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2'-hydroxyformononetin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1ccc(c(c1)O)c1coc2c(c1=O)ccc(c2)O
InChI	InChI=1S/C16H12O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-8,17-18H,1H3
InChIKey	XKHHKXCBFHUOHM-UHFFFAOYSA-N
Formula	C₁₆H₁₂O₅
HBA	5
HBD	2
MW	284.27
Rotatable Bonds	2
TPSA	79.9
LogP	2.88
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.06
Exact Mass	284.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Millettia macrophylla	Leguminosae/Fabaceae	Plantae	1712208

Showing of synonyms

Zingue S, Tchoumtchoua J, et al. (2016). Estrogenic and cytotoxic potentials of compounds isolated from Millettia macrophylla Benth (Fabaceae): towards a better understanding of its underlying mechanisms.. BMC complementary and alternative medicine,2016, 16(1), 421. [View] [PubMed]

Pubchem: 5280551

Cas: 1890-99-9

Kegg Ligand: C02920

Chebi: 17678

Nmrshiftdb2: 60069690

Chembl: CHEMBL253514

Comptox: DTXSID30415062

No compound-protein relationship available.

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 284.27 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 284.27 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 284.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.740
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.180
Plasma Protein Binding: 77.81
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 3.990
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.830
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.440
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.990
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.040
Rat (Acute): 2.160
Rat (Chronic Oral): 2.430
Fathead Minnow: 4.650
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 443.950
Hydration Free Energy: -12.210
Log(D) at pH=7.4: 2.870
Log(P): 3.28
Log S: -5.35
Log(Vapor Pressure): -7.79
Melting Point: 244.15
pKa Acid: 7.61
pKa Basic: 4.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9732
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9688
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9546
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.9468
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9461
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.9424
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.9421
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.9419
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9398
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9334
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.9332
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9331
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.9316
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	4	0.9298
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9266
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9248
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9219
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9211
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.9158
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9131
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.9095
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.9088
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9079
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9050
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9044
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9001
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.8988
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8983
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8943
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8930
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8920
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8897
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.8874
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8851
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8850
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.8846
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8845
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.8808
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8752
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8729
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8710
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8709
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8708
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8679
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8676
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8660
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8645
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8623
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8619
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8608
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8605
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8593
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8563
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8546
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.8526
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8525
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.8494
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.8483
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.8470
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8467
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.8462
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8454
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8448
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.8445
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.8431
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8410
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8371
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8364
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8348
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8325
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8315
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8304
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8301
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	3	0.8279
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.8251
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8238
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8236
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8223
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8218
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8201
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	3	0.8201
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.8200
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8189
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8181
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.8121
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.8121
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.8118
Bromodomain protein, putative	Q8I240	Q8I240_PLAF7	Plasmodium falciparum	5	0.8114
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8103
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8091
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8070
Acetolactate synthase catalytic subunit, mitochondrial	P07342	ILVB_YEAST	Saccharomyces cerevisiae	3	0.8065
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.8054
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8054
Enoyl-ACP reductase	Q9BH77	Q9BH77_PLAFA	Plasmodium falciparum	3	0.8053
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8046
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8031
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8020
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8012
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7979
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7967
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7966
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.7945
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7940
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7932
Calmodulin-like domain protein kinase isoenzyme gamma, related	F0V9W9	F0V9W9_NEOCL	Neospora caninum	3	0.7927
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7926
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	3	0.7924
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7874
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7868
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7860
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7848
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7825
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	3	0.7816
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7815
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7806
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7779
Terminal oxygenase component of carbazole	Q84II6	Q84II6_JANS3	Janthinobacterium sp	3	0.7768
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7762
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7760
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7742
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.7741
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7735
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7712
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7705
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7702
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7693
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7691
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7690
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7681
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7638
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7636
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	3	0.7632
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7625
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7614
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7594
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7589
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7573
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7570
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7561
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7555
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7547
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7547
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7532
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7529
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7526
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7523
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7516
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7515
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7512
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7507
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7502
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7501
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.7489
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7482
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7473
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7462
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7455
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	3	0.7453
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7451
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7439
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7438
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7434
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7431
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7431
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7430
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7428
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7415
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7408
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7405
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7402
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7401
Pyruvate dehydrogenase [ubiquinone]	P07003	POXB_ECOLI	Escherichia coli	3	0.7401
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7399
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7396
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7391
Acetyl-CoA carboxylase	Q00955	ACAC_YEAST	Saccharomyces cerevisiae	4	0.7388
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7387
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7379
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7379
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7365
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7360
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7357
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	4	0.7352
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7348
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7344
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7338
Estrogen receptor beta	Q92731	ESR2_HUMAN	Homo sapiens	3	0.7337
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7335
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7331
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7330
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7320
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7319
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7319
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7298
Enoyl-acyl carrier protein reductase	Q6TEI5	Q6TEI5_PLABE	Plasmodium berghei	3	0.7296
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7296
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7289
Putative N-acetyl glucosaminyl transferase	Q6U8B0	Q6U8B0_RAOTE	Raoultella terrigena	3	0.7270
Thiamin pyrophosphokinase 1	Q9R0M5	TPK1_MOUSE	Mus musculus	3	0.7269
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7269
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7268
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7267
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7264
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7262
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7258
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7251
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7250
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7248
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7235
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7229
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7224
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	4	0.7223
Serine hydroxymethyltransferase	Q7SIB6	Q7SIB6_GEOSE	Geobacillus stearothermophilus	3	0.7214
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7214
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7203
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7203
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7199
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7195
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7191
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7190
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7189
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7187
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7168
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7167
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7161
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7160
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7159
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7159
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7156
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7149
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7149
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7148
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7145
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7145
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7144
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7139
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7133
Beta-glucosidase 12	B8AVF0	BGL12_ORYSI	Oryza sativa subsp. indica	2	0.7124
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7120
Thiamine-binding periplasmic protein	P31550	THIB_ECOLI	Escherichia coli	3	0.7118
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7116
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7115
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7109
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7109
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7107
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7102
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7100
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7097
Peptide deformylase 1B, chloroplastic/mitochondrial	Q9FUZ2	DEF1B_ARATH	Arabidopsis thaliana	3	0.7090
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7086
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7085
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7078
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7076
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7069
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7065
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7059
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7051
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7050
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7049
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7048
Estrogen receptor beta	Q62986	ESR2_RAT	Rattus norvegicus	4	0.7036
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7036
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7033
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7032
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7031
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7030
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7030
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7025
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7025
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7017
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	2	0.7016
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7014
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7013
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7012
Pentalenic acid synthase	Q825I8	CYP28_STRAW	Streptomyces avermitilis	2	0.7008
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.7007
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7005
Alpha-2,3/2,6-sialyltransferase/sialidase	Q15KI8	Q15KI8_PASMD	Pasteurella multocida	4	0.7001
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7001

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