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(8′-alpha,9′-beta-dihydroxy)-3-farnesylindole

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	C/C(=C\Cc1c[nH]c2c1cccc2)/CC/C=C(/[C@H]([C@H](C=C(C)C)O)O)\C
InChI	InChI=1S/C23H31NO2/c1-16(2)14-22(25)23(26)18(4)9-7-8-17(3)12-13-19-15-24-21-11-6-5-10-20(19)21/h5-6,9-12,14-15,22-26H,7-8,13H2,1-4H3/b17-12+,18-9+/t22-,23+/m0/s1
InChIKey	RWUFSDSPFFBHHT-ITUBUZOLSA-N
Formula	C₂₃H₃₁NO₂
HBA	2
HBD	3
MW	353.51
Rotatable Bonds	8
TPSA	56.25
LogP	5.07
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	353.24
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Uvaria pandensis	Annonaceae	Plantae	673193

Showing of synonyms

Maeda G, Gilissen PJ, et al. (2021). Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis. Journal of natural products,2021, 84(12), 3080-3089. [View] [PubMed]

Pubchem: 162642184

Chembl: CHEMBL5278583

No compound-protein relationship available.

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 353.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.45
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -3.03

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.14
Plasma Protein Binding: 52.61
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: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.67
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.75
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.54
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.59
Micronucleos: Toxic
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: Safe
T. Pyriformis: -2.04
Rat (Acute): 2.89
Rat (Chronic Oral): 2.5
Fathead Minnow: 5.32
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 406.99
Hydration Free Energy: -9.25
Log(D) at pH=7.4: 4.14
Log(P): 4.93
Log S: -4.65
Log(Vapor Pressure): -8.71
Melting Point: 114.73
pKa Acid: 11.24
pKa Basic: 6.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9326
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9269
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9192
Albumin	P02769	ALBU_BOVIN	Bos taurus	3	0.9181
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9158
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9132
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9092
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9057
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9013
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8974
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8972
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.8911
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.8904
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.8889
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8830
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	4	0.8813
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8737
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8722
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.8673
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8661
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8600
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8590
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8566
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.8540
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8510
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8509
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8448
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8430
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8396
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8341
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8239
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8234
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8208
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.8195
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8189
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.8181
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8170
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8120
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.8117
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.8104
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8076
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.8054
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8021
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8016
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8010
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7965
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7950
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7941
Nuclear receptor ROR-alpha	P35398	RORA_HUMAN	Homo sapiens	4	0.7936
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7935
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7929
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7918
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7917
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7907
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7900
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7894
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7891
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7884
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7873
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7872
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7871
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7871
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7865
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7853
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7838
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7821
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7816
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7809
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7805
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7803
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7801
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7801
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7798
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7780
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7779
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7769
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.7765
Casein kinase I isoform gamma-2	P78368	KC1G2_HUMAN	Homo sapiens	3	0.7758
Quorum-sensing transcriptional activator	Q8XBD0	Q8XBD0_ECO57	Escherichia coli O157:H7	3	0.7749
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	2	0.7740
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7719
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7718
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7711
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7709
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7705
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7702
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7676
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7676
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7673
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7670
Naphthalene 1,2-dioxygenase system, large oxygenase component	P0A110	NDOB_PSEPU	Pseudomonas putida	2	0.7665
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR0	INHA_MYCTO	Mycobacterium tuberculosis	3	0.7660
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7658
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7655
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7653
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7647
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7645
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7642
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7638
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	2	0.7637
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7636
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7636
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	3	0.7634
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7634
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7633
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7632
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7629
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7627
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	2	0.7625
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7618
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7618
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7618
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7617
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	2	0.7616
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	2	0.7612
Trichosurin	Q29147	TRIC_TRIVU	Trichosurus vulpecula	2	0.7605
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7605
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7605
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	2	0.7600
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7597
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7593
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7584
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7581
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7580
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7579
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7578
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7574
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7573
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7568
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	2	0.7566
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7565
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7565
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7564
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7561
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7557
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7555
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7550
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7549
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7541
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7539
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7535
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	2	0.7533
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7521
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7517
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7512
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7511
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7501
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7498
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7497
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7494
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7490
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7490
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7489
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7483
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7478
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7476
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7473
Thyroid hormone receptor alpha	P04625	THA_CHICK	Gallus gallus	3	0.7470
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	4	0.7468
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7468
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7459
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7452
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7450
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7449
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	5	0.7447
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7445
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7444
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	2	0.7437
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7434
Cytochrome P450 3A4	P08684	CP3A4_HUMAN	Homo sapiens	3	0.7433
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7433
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	2	0.7430
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7425
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7422
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7420
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7419
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7418
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7417
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7416
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7413
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7412
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7408
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7405
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7404
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7401
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7400
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7399
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7397
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7390
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7386
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7386
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7382
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7381
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7380
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7380
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7380
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7379
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7378
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7375
Lactoylglutathione lyase	Q04760	LGUL_HUMAN	Homo sapiens	2	0.7375
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7374
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7372
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7367
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7366
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7364
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	2	0.7358
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7356
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7354
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7344
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7343
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7343
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7340
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7340
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7339
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7335
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7335
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	2	0.7322
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7321
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7319
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7315
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7308
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7306
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7302
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7298
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	2	0.7298
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7298
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7283
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7283
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7279
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7276
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7275
C-C chemokine receptor type 5	P51681	CCR5_HUMAN	Homo sapiens	3	0.7267
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7267
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7265
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7262
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7260
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7259
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7256
Actin, alpha skeletal muscle	P68135	ACTS_RABIT	Oryctolagus cuniculus	3	0.7250
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7250
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7246
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	2	0.7246
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7241
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7236
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7236
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7234
Regulatory protein SdiA	P07026	SDIA_ECOLI	Escherichia coli	3	0.7226
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7225
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7224
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7222
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7221
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7220
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7212
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7212
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7207
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7206
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	2	0.7203
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7202
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	2	0.7200
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7198
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7197
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7195
Albumin	P14639	ALBU_SHEEP	Ovis aries	2	0.7195
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7195
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7194
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7192
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	2	0.7188
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7187
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7185
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7183
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7181
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7175
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7171
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7168
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7165
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7160
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	3	0.7149
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7148
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7144
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	2	0.7143
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	4	0.7140
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7139
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	2	0.7133
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7131
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7130
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7130
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7127
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7124
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7122
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	2	0.7120
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7117
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7116
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7111
Death-associated protein kinase 3	O43293	DAPK3_HUMAN	Homo sapiens	2	0.7108
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7104
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7103
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7093
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7089
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	2	0.7087
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7081
Methyl-branched lipid omega-hydroxylase	P9WPP3	CP124_MYCTU	Mycobacterium tuberculosis	3	0.7075
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7073
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7070
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7066
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7065
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7064
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7061
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7061
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7061
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7060
Chorismate pyruvate-lyase	P26602	UBIC_ECOLI	Escherichia coli	2	0.7060
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7058
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	2	0.7056
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	2	0.7055
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7054
Purine nucleoside phosphorylase, putative	A2E7Y6	A2E7Y6_TRIVA	Trichomonas vaginalis	2	0.7053
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7047
Abscisic acid receptor PYL9	Q5Z8S0	PYL9_ORYSJ	Oryza sativa subsp. japonica	3	0.7046
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7045
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7042
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7039
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7038
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7038
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7037
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.7034
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	2	0.7034
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7033
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7030
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	2	0.7029
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7026
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7026
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7023
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7021
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7014
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7014
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	2	0.7013
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7012
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7011
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7010
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	2	0.7007
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7007
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7006
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7002
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.7001

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