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Tetrahydroauroglaucin

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Benzenoid

Canonical Smiles	CCCCC/C=C/c1c(O)cc(c(c1C=O)O)CC=C(C)C
InChI	InChI=1S/C19H26O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h8-10,12-13,21-22H,4-7,11H2,1-3H3/b9-8+
InChIKey	FYGPFTSGVSZKAJ-CMDGGOBGSA-N
Formula	C₁₉H₂₆O₃
HBA	3
HBD	2
MW	302.41
Rotatable Bonds	8
TPSA	57.53
LogP	5.01
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	302.19
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ammi majus	Umbelliferae	Plantae	48026

Showing of synonyms

Fathallah N, Raafat M.M, et al. (2019). Bio-Guided Fractionation of Prenylated Benzaldehyde Derivatives as Potent Antimicrobial and Antibiofilm from Ammi majus L. Fruits-Associated Aspergillus amstelodami. Molecules, 2019,24(22),4114. [View] [PubMed]

Pubchem: 14355117

Cas: 40434-07-9

Zinc: ZINC000013374441

Chebi: 68189

Nmrshiftdb2: 70003835

Metabolights: MTBLC68189

Chembl: CHEMBL1811938

Bindingdb: 50350092

No compound-protein relationship available.

SMILES: c1ccccc1

Level: 0

Mol. Weight: 302.41 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -4.78
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.4
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.5
Plasma Protein Binding: 31.77
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.07
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.51
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.14
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.17
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 4.66
Rat (Acute): 1.92
Rat (Chronic Oral): 2.37
Fathead Minnow: 4.57
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 368.59
Hydration Free Energy: -8.38
Log(D) at pH=7.4: 3.87
Log(P): 6.17
Log S: -4.9
Log(Vapor Pressure): -6.68
Melting Point: 78.55
pKa Acid: 8.53
pKa Basic: 5.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.9433
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9347
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9120
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9014
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8979
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8953
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8928
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8899
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8897
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8897
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8731
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8669
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8659
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8647
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8587
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8544
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8411
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8404
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8315
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8298
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8263
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8253
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8249
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.8181
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8104
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8101
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.8096
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8081
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8071
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.8046
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8036
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8030
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.8028
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.8004
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8000
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7994
tRNA-guanine(15) transglycosylase	O58843	ATGT_PYRHO	Pyrococcus horikoshii	3	0.7955
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7955
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7954
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7948
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7934
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7921
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7908
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7902
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7901
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	3	0.7894
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7882
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7872
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7869
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7867
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7865
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7847
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7844
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7839
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7830
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7816
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7803
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7798
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7795
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7793
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7784
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.7770
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7744
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7742
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7740
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7719
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7714
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7711
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7709
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7708
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7706
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7700
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7699
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7692
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7692
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.7691
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7682
Japanin	M1MR49	M1MR49_RHIAP	Rhipicephalus appendiculatus	3	0.7667
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7650
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7640
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7634
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7626
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7625
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	4	0.7608
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7596
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7582
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7558
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7546
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7543
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7533
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7529
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7528
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7528
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7518
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7504
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	P62617	ISPF_ECOLI	Escherichia coli	3	0.7482
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7479
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7457
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7445
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7429
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7427
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7425
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7415
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7414
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7408
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7407
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7406
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7405
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7398
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7396
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7376
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7369
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7365
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7361
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7356
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7343
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7342
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7321
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7320
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7319
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7308
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7306
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7299
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7294
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7290
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7286
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7283
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7281
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7267
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7267
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7255
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7250
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7248
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7243
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7242
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7240
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7240
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7239
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7235
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7235
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7234
Metallo-beta-lactamase type 2	P26918	BLAB_AERHY	Aeromonas hydrophila	2	0.7229
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7228
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7227
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7226
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	3	0.7220
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7217
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7208
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7206
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7201
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7201
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7197
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7195
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7194
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7194
Lanosterol 14-alpha demethylase CYP51	P10614	CP51_YEAST	Saccharomyces cerevisiae	3	0.7186
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7185
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7181
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7152
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7144
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7142
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7141
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7139
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7124
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7113
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	2	0.7112
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7112
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	2	0.7110
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7106
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7104
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7091
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7080
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7072
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7069
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7067
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7065
Alpha/beta hydrolase fold	A5VAT9	A5VAT9_SPHWW	Sphingomonas wittichii	2	0.7058
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7056
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7055
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7049
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	2	0.7046
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7044
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7024
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7023
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7014
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	3	0.7011
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7002

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