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Marmesin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
- Class: Coumarin
| Canonical Smiles | O=c1ccc2c(o1)cc1c(c2)C[C@H](O1)C(O)(C)C |
|---|---|
| InChI | InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m0/s1 |
| InChIKey | FWYSBEAFFPBAQU-LBPRGKRZSA-N |
| Formula | C14H14O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 246.26 |
| Rotatable Bonds | 1 |
| TPSA | 59.67 |
| LogP | 1.87 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.36 |
| Exact Mass | 246.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Pituranthos triradiatus | Apiaceae | Plantae | 99500 |
| 2 | Ammi majus | Apiaceae | Plantae | 48026 |
| 3 | Ammi majus | Apiaceae | Plantae | 48026 |
| 4 | Citrus reticulata | Rutaceae | Plantae | 85571 |
Showing of synonyms
Marmesin
13849-08-6
S-(+)-Marmesin
(+)-Marmesin
(S)-Marmesin
MARMESIN, (+)-
CCRIS 5728
CHEBI:6695
H5D33D6K5D
(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (2S)-
NSC 340840
NSC-340840
UNII-H5D33D6K5D
HSDB 8478
(2S)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
(S)-(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
(S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-
7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-
7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 2,3-DIHYDRO-2-(1-HYDROXY-1-METHYLETHYL)-, (2S)-
CHEBI:49080
(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro(3,2-g)chromen-7-one
(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one
(2S)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one
(S)-(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one
(S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one
7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-
7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-
2-(2-Hydroxy-2-propanyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one
7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-
2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7h-furo(3,2-g)chromen-7-one
2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7h-furo[3,2-g]chromen-7-one
Fwysbeaffpbaqu-lbprgkrzsa-n
(7S)-marmesin
(S)-2-(2-Hydroxypropan-2-yl)-2H-furo[3,2-g]chromen-7(3H)-one
(S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
CHEMBL442813
S(+)-Marmesin
MFCD01725701
Spectrum_001516
SpecPlus_000918
Spectrum2_000737
Spectrum3_001642
Spectrum4_001701
Spectrum5_000402
Marmesin ((+)-Marmesin)
BSPBio_003363
KBioGR_002022
KBioSS_001996
DivK1c_007014
S-(+)-Marmesin (Standard)
SPBio_000694
MEGxp0_001933
2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one #
SCHEMBL12062107
HY-N2176R
KBio1_001958
KBio2_001996
KBio2_004564
KBio2_007132
KBio3_002583
DTXSID001030448
HY-N2176
BDBM50250917
CCG-40145
NSC340840
NSC796156
S3283
AKOS021983162
CS-7901
FM74296
NSC-796156
SDCCGMLS-0066759.P001
AC-35105
DA-65255
MS-23486
NS00094519
C09276
AB00053150-02
BRD-K36377456-001-02-0
Q13847605
7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-
7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-
2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE
7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
(2S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
(2S)-2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE
NCGC00178117-02!(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
- Selim YA, Ouf NH. (2012). Anti-inflammatory new coumarin from the Ammi majus L.. Organic and Medicinal Chemistry Letters,2012,2,1. [View] [PubMed]
- Halim AF, Lahioub MF, et al. (1989). Coumarins of Pituranthos triradiatus Growing in Egypt. Planta Medica,1989,55,609. [View]
- Abu-Mustafa EA, Fayez MBE (1961). Natural coumarins I. marmesin and marmesinin, further products from the fruits of Ammi majus L.. The Journal of Organic Chemistry,1961,26(1),161-166. [View]
- 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:
334704
Cas:
13849-08-6
Gnps:
CCMSLIB00000847820
Zinc:
ZINC000000051924
Kegg Ligand:
C09276
Chebi:
6695
Nmrshiftdb2:
60021224
Chembl:
CHEMBL442813
Bindingdb:
50250917
CPRiL:
132670
SMILES: C1COc(c12)cc3c(c2)ccc(=O)o3
Level: 0
Mol. Weight: 246.26 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.140
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.17
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.820
- Plasma Protein Binding
- 61.18
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-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
- Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.790
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.390
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.140
- 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
- 2.330
- Rat (Acute)
- 2.360
- Rat (Chronic Oral)
- 1.390
- Fathead Minnow
- 4.160
- 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
- 365.610
- Hydration Free Energy
- -10.480
- Log(D) at pH=7.4
- 1.600
- Log(P)
- 1.7
- Log S
- -2.95
- Log(Vapor Pressure)
- -6.62
- Melting Point
- 210.87
- pKa Acid
- 6.77
- pKa Basic
- 6.02
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.9229 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.9229 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 4 | 0.9036 |
| [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial | Q15119 | PDK2_HUMAN | Homo sapiens | 4 | 0.9036 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8831 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.8831 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8792 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8792 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8783 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8783 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8783 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.8783 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8747 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8747 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8732 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8732 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8729 |
| NADH:flavin oxidoreductase Sye1 | Q8EEC8 | Q8EEC8_SHEON | Shewanella oneidensis | 3 | 0.8729 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8669 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.8669 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8626 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8626 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.8552 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.8552 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8515 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8515 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8496 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.8496 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8452 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8452 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8419 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8419 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8374 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8374 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8369 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8369 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8341 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8341 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8313 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8313 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8311 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8311 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8260 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8260 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8157 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8157 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8152 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8152 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8121 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8121 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8048 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8048 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.8048 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.8048 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8044 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8044 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8032 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8032 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7917 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7917 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7894 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7894 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7795 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7795 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7790 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7790 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7780 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7780 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7768 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7768 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7766 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7766 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.7761 |
| Sulfotransferase 1A1 | P50225 | ST1A1_HUMAN | Homo sapiens | 3 | 0.7761 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7758 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7758 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7736 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7736 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7722 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7722 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7702 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7702 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7693 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7693 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7683 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7683 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7671 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7671 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7622 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7622 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7612 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7612 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 4 | 0.7575 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 4 | 0.7575 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7573 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7573 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7569 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7569 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7567 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7567 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7565 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7565 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7562 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7562 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7556 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7556 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7527 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7527 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7520 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7520 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7494 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7494 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7489 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7489 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7479 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7479 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7473 |
| Carminomycin 4-O-methyltransferase DnrK | Q06528 | DNRK_STRPE | Streptomyces peucetius | 2 | 0.7473 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7460 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 2 | 0.7460 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7455 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7455 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7454 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7454 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7444 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7444 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7436 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 2 | 0.7436 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7410 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7410 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7393 |
| Protein LlR18A | P52778 | L18A_LUPLU | Lupinus luteus | 3 | 0.7393 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7385 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7385 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7338 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7338 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7328 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7328 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7323 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7323 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7308 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7308 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7295 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 3 | 0.7295 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7292 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 4 | 0.7292 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7291 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7291 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7290 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7290 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7275 |
| Pantothenate synthetase | P9WIL4 | PANC_MYCTO | Mycobacterium tuberculosis | 2 | 0.7275 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7267 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7267 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7256 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7256 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7253 |
| Ribonuclease TTHA0252 | Q5SLP1 | RNSE_THET8 | Thermus thermophilus | 3 | 0.7253 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7214 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.7214 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7204 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7204 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7191 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7191 |
| Biotin carboxylase | P24182 | ACCC_ECOLI | Escherichia coli | 2 | 0.7191 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7191 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7179 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 2 | 0.7179 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7169 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7169 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7169 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 2 | 0.7169 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7162 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7162 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 2 | 0.7154 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 2 | 0.7154 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7153 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7153 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7145 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7145 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7130 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7130 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7127 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7127 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7123 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 2 | 0.7123 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7116 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7116 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7114 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7114 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7110 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7110 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7089 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7089 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7084 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 3 | 0.7084 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7079 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7079 |
| DNA double-strand break repair protein Mre11 | Q9X1X0 | Q9X1X0_THEMA | Thermotoga maritima MSB8 | 3 | 0.7079 |
| DNA double-strand break repair protein Mre11 | Q9X1X0 | Q9X1X0_THEMA | Thermotoga maritima MSB8 | 3 | 0.7079 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7070 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7070 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7070 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7070 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7064 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7064 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7052 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7052 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 4 | 0.7044 |
| Sulfide-quinone reductase | B7JBP8 | SQRD_ACIF2 | Acidithiobacillus ferrooxidans) | 4 | 0.7044 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 3 | 0.7040 |
| RNA polymerase sigma factor SigA | Q5SKW1 | Q5SKW1_THET8 | Thermus thermophilus | 3 | 0.7040 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7039 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7039 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7037 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7037 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7037 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7037 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7023 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7023 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7015 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7015 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7012 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7012 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7012 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7012 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 2 | 0.7010 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 2 | 0.7010 |