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Ophrypetalin

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Acetogenin

Canonical Smiles	CCCCCC[C@@H](CCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@@H](CCCCCCCCCCCCC1=C[C@@H](OC1=O)C)O)O)O
InChI	InChI=1S/C37H66O7/c1-3-4-5-15-19-30(38)20-17-22-32(40)34-24-26-36(44-34)35-25-23-33(43-35)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3/t28-,30-,31+,32-,33+,34+,35+,36+/m0/s1
InChIKey	DAEFUOXKPZLQMM-AUDZWCKFSA-N
Formula	C₃₇H₆₆O₇
HBA	7
HBD	3
MW	622.93
Rotatable Bonds	25
TPSA	105.45
LogP	7.86
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.92
Exact Mass	622.48
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ophrypetalum odoratum	Annonaceae	Plantae	489344

Showing of synonyms

Sung'hwa F, Mgina CA, et al. (1999). Ophrypetalin and other annonaceous acetogenins from Ophrypetalum odoratum. Natural Product Letters,1999,13(3),195-202. [View] [PubMed]

Pubchem: 441612

Cas: 120298-30-8

Zinc: ZINC000004097661

Kegg Ligand: C08545

Chebi: 9246

Nmrshiftdb2: 60075625

Chembl: CHEMBL41177

Comptox: DTXSID80152793

Bindingdb: 50087503

CPRiL: 251184

SMILES: O=C1OCC=C1CCCCCCCCCCCCCC2CCC(O2)C3CCCO3

Level: 2

Mol. Weight: 622.93 g/mol

SMILES: O1CCCC1CCCCCCCCCCCCCC2=CCOC2=O

Level: 1

Mol. Weight: 622.93 g/mol

SMILES: O1CCCC1C2CCCO2

Level: 1

Mol. Weight: 622.93 g/mol

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 622.93 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 622.93 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.05
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.85
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 14.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.46
Plasma Protein Binding: 82.23
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 1.58
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.0
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -2.84
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 4.97
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: -33788.71
Rat (Acute): 3.08
Rat (Chronic Oral): 2.51
Fathead Minnow: 57.74
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 1624.2
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 4.43
Log(P): 8.39
Log S: -5.53
Log(Vapor Pressure): -31.9
Melting Point: 64.94
pKa Acid: 9.21
pKa Basic: 5.65

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9467
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9467
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9450
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9450
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.9423
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.9423
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9378
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9378
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9372
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9372
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9268
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.9268
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9251
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9251
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9194
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9194
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9016
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9016
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8901
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8901
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8896
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8896
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8821
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8821
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8774
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8774
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8752
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8752
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8722
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8722
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8665
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8665
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8651
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8651
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8617
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8617
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8611
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8611
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8608
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8608
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.8590
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.8590
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8574
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8574
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8527
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8527
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8449
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8449
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8443
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8443
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8439
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8439
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8334
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8334
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8328
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8328
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8326
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8326
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8321
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8321
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8315
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8315
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.8256
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.8256
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.8252
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.8252
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.8245
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.8245
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8243
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8243
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8220
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8220
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.8204
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.8204
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8109
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8109
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8076
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8076
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8041
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8041
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8036
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8036
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7993
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7993
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7974
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7974
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7955
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7955
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7951
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7951
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7941
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7941
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7936
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7936
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7933
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7933
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7920
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7920
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7902
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7902
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7900
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7900
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7886
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7886
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7868
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7868
Gibberellin receptor GID1	Q6L545	GID1_ORYSJ	Oryza sativa subsp. japonica	3	0.7857
Gibberellin receptor GID1	Q6L545	GID1_ORYSJ	Oryza sativa subsp. japonica	3	0.7857
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7852
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7852
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7841
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7841
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7839
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.7839
Fluoroacetyl-CoA thioesterase	Q1EMV2	FLK_STRCT	Streptantibioticus cattleyicolor	3	0.7838
Fluoroacetyl-CoA thioesterase	Q1EMV2	FLK_STRCT	Streptantibioticus cattleyicolor	3	0.7838
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7829
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7829
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7828
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7828
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7794
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7794
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7779
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7779
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7770
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7770
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7765
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7765
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7764
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7764
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7731
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7731
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7718
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7718
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	3	0.7656
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	3	0.7656
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7614
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7614
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7578
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7578
4-alpha-glucanotransferase	O87172	MALQ_THETH	Thermus thermophilus	3	0.7574
4-alpha-glucanotransferase	O87172	MALQ_THETH	Thermus thermophilus	3	0.7574
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7569
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7569
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.7550
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.7550
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7519
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7519
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7513
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.7513
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7502
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7502
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7496
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7496
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7484
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7484
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7468
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7468
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7464
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7464
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7461
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7461
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7455
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7455
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7437
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7437
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7427
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7427
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7397
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	4	0.7397
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7390
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7390
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7387
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7387
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7365
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7365
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7364
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7364
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7362
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	2	0.7362
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7349
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7349
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7349
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7349
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7343
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7343
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7341
Alanine aminotransferase	Q9P9M8	Q9P9M8_9EURY	Pyrococcus furiosus	2	0.7341
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7340
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7340
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7336
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7336
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7334
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7334
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7319
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7319
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7316
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7316
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7308
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7308
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7295
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7295
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7287
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7287
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7263
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7263
Gibberellin receptor GID1A	Q9MAA7	GID1A_ARATH	Arabidopsis thaliana	3	0.7260
Gibberellin receptor GID1A	Q9MAA7	GID1A_ARATH	Arabidopsis thaliana	3	0.7260
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7248
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7248
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	2	0.7241
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	2	0.7241
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7238
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7238
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	3	0.7237
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	3	0.7237
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7226
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7226
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.7224
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.7224
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7220
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7220
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7218
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7218
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7214
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7214
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7213
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7213
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7201
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7201
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7200
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7200
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7195
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7195
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7184
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7184
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7182
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7182
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7179
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7179
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7169
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7169
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7161
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7161
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7155
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7155
Androgen receptor	P19091	ANDR_MOUSE	Mus musculus	3	0.7145
Androgen receptor	P19091	ANDR_MOUSE	Mus musculus	3	0.7145
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.7134
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.7134
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7127
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7127
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7125
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7125
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7122
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	2	0.7122
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7122
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7122
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7120
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7120
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7113
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7113
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7112
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7112
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7111
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7111
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7111
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7111
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7109
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7109
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7106
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7106
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7105
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7105
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7100
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7100
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7098
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7098
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7093
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7093
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7092
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7092
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7089
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7089
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7088
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7088
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7068
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7068
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7067
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7067
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7066
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7066
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7058
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	2	0.7058
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7058
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7058
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7042
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7042
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7036
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7036
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7032
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7032
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7032
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7032
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7015
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7015
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7013
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7013
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7007
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7007
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7007
Androgen receptor	O97775	ANDR_PANTR	Pan troglodytes	3	0.7007
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7005
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7005
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7002
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7002

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