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(R)-byakangelic

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Furocoumarin

Canonical Smiles	COc1c2ccoc2c(c2c1ccc(=O)o2)OC[C@@H](C(O)(C)C)O
InChI	InChI=1S/C17H18O7/c1-17(2,20)11(18)8-23-16-14-10(6-7-22-14)13(21-3)9-4-5-12(19)24-15(9)16/h4-7,11,18,20H,8H2,1-3H3/t11-/m0/s1
InChIKey	PKRPFNXROFUNDE-NSHDSACASA-N
Formula	C₁₇H₁₈O₇
HBA	7
HBD	2
MW	334.32
Rotatable Bonds	5
TPSA	102.27
LogP	2.06
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	334.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Citrus reticulata	Rutaceae	Plantae	85571

Showing of synonyms

Fomani M, Ngeufa Happi E, et al. (2016). Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco).. Bioorganic & medicinal chemistry letters,2016, 26(2), 306-309. [View] [PubMed]

Pubchem: 5315583

Zinc: ZINC000013380829

Nmrshiftdb2: 70129500

No compound-protein relationship available.

SMILES: c1coc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 334.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.7
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.43
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 73.36
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.31
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.32
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.26
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.96
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: 0.23
Rat (Acute): 2.52
Rat (Chronic Oral): 2.47
Fathead Minnow: 4.45
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 441.53
Hydration Free Energy: -12.19
Log(D) at pH=7.4: 1.89
Log(P): 1.56
Log S: -3.11
Log(Vapor Pressure): -8.33
Melting Point: 155.17
pKa Acid: 6.63
pKa Basic: 6.08

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9434
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9398
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9319
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9213
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.9064
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8996
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8947
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8878
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8673
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8658
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8614
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8614
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8481
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8442
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8333
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8266
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8171
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8165
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.8131
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.8129
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8124
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.8108
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8087
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8058
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8008
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7980
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7958
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7957
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7931
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7907
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7879
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7867
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7840
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7836
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7795
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	3	0.7794
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7788
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7785
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7782
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7770
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7767
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7754
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7742
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7724
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7720
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.7711
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7695
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7693
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7683
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7667
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7663
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7653
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	3	0.7639
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7637
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7610
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7607
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7599
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7598
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7597
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7596
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7593
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7592
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	3	0.7591
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7588
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7563
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7545
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7540
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7536
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7527
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7527
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7518
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7512
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7494
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7490
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7477
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7468
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7468
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.7467
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7462
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	2	0.7459
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7455
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7454
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7433
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7423
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7416
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	2	0.7416
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7407
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7407
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7397
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7386
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7380
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	2	0.7374
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7369
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	4	0.7364
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7364
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7361
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7361
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7360
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7359
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7358
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7353
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7350
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7318
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7317
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	4	0.7302
Diguanylate phosphodiesterase	A6T8V8	A6T8V8_KLEP7	Klebsiella pneumoniae subsp. pneumoniae	4	0.7298
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7296
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7288
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7286
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7285
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7282
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7279
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7269
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7268
Pyridoxal kinase	P82197	PDXK_SHEEP	Ovis aries	3	0.7265
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7263
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7263
Casein kinase I isoform gamma-2	P78368	KC1G2_HUMAN	Homo sapiens	3	0.7256
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7251
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7245
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7243
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7236
Pol polyprotein	P32542	POL_EIAVC	Equine infectious anemia virus	4	0.7228
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7222
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7219
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7200
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7197
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7194
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7181
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7179
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7175
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7171
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7160
Acetyl-CoA carboxylase	Q00955	ACAC_YEAST	Saccharomyces cerevisiae	3	0.7157
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7155
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7146
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7143
Phospholipase A2, membrane associated	P14555	PA2GA_HUMAN	Homo sapiens	2	0.7141
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7140
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7133
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.7129
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7128
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7124
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7123
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7122
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7118
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7112
Thymidylate synthase	P45352	TYSY_RAT	Rattus norvegicus	2	0.7108
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7107
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7106
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7093
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7093
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7079
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7078
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7077
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	2	0.7077
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7069
Alpha/beta hydrolase fold	A5VAT9	A5VAT9_SPHWW	Sphingomonas wittichii	2	0.7069
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7065
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7057
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7056
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7053
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7052
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7047
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	2	0.7046
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7045
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7041
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7034
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7024
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	2	0.7018
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7014
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7013
Protoporphyrinogen oxidase, mitochondrial	O24164	PPOM_TOBAC	Nicotiana tabacum	2	0.7010
FMN-binding protein	Q46604	FMNB_DESVM	Nitratidesulfovibrio vulgaris	5	0.7007
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7004

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