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Chrysophanol
- Family: Plantae - Liliaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Anthraquinone
| Canonical Smiles | Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1 |
|---|---|
| InChI | InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3 |
| InChIKey | LQGUBLBATBMXHT-UHFFFAOYSA-N |
| Formula | C15H10O4 |
| HBA | 4 |
| HBD | 2 |
| MW | 254.24 |
| Rotatable Bonds | 0 |
| TPSA | 74.6 |
| LogP | 2.18 |
| Number Rings | 3 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.07 |
| Exact Mass | 254.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aloe sinkatana | Asphodelaceae | Plantae | 210945 |
| 2 | Aloe dawei | Asphodelaceae | Plantae | 1331517 |
| 3 | Kniphofia foliosa | Asphodelaceae | Plantae | 214838 |
| 4 | Aloe secundiflora | Asphodelaceae | Plantae | 1593107 |
| 5 | Bulbine abyssinica | Asphodelaceae | Plantae | 2511937 |
| 6 | Aloe berhana | Asphodelaceae | Plantae | 1593069 |
| 7 | Aloe rivae | Asphodelaceae | Plantae | 1811902 |
| 8 | Aloe megalacantha | Asphodelaceae | Plantae | 1389516 |
| 9 | Aloe pulcherima | Asphodelaceae | Plantae | 3161391 |
| 10 | Aloe saponaria | Asphodelaceae | Plantae | 1155789 |
| 11 | Senna didymobotrya | Leguminosae/Fabaceae | Plantae | 72401 |
| 12 | Senna floribunda | Leguminosae/Fabaceae | Plantae | 2601732 |
| 13 | Senna septemtrionalis | Leguminosae/Fabaceae | Plantae | 346998 |
| 14 | Senna Didymobotrya | Leguminosae/Fabaceae | Plantae | 72401 |
| 15 | Rumex abysinicus | Polygonaceae | Plantae | 273505 |
| 16 | Rhamnus prinoides | Rhamnaceae | Plantae | 280022 |
| 17 | Aloe pulcherrima | Asphodelaceae | Plantae | 3161391 |
| 18 | Aloe berhana | Asphodelaceae | Plantae | 1593069 |
| 19 | Kniphofia species | Liliaceae | Plantae | 49723 |
| 20 | Aloe graminicola | Liliaceae | Plantae | 330741 |
| 21 | Kniphofia species | Liliaceae | Plantae | 49723 |
| 22 | Aloe species | Liliaceae | Plantae | 117795 |
| 23 | Kniphofia foliosa | Liliaceae | Plantae | 214838 |
| 24 | Rumex usambarensis | Polygonaceae | Plantae | 2984668 |
| 25 | Rumex abyssinicus | Polygonaceae | Plantae | 273505 |
| 26 | Rumex crispus | Polygonaceae | Plantae | 174649 |
| 27 | Rumex bequaerrii | Polygonaceae | Plantae | 3618 |
| 28 | Rumex ruwenzoriensis | Polygonaceae | Plantae | 3618 |
| 29 | Rumex abysinica | Polygonaceae | Plantae | 3618 |
| 30 | Kniphofia foliosa | Asphodelaceae | Plantae | 214838 |
| 31 | Kniphofia reflexa | Asphodelaceae | Plantae | 49723 |
| 32 | Asphodelus microcarpus | Liliaceae | Plantae | 49697 |
Showing of synonyms
Chrysophanol
481-74-3
CHRYSOPHANIC ACID
3-Methylchrysazin
C.I. Natural Yellow 23
NSC 37132
1,8-Dihydroxy-3-methyl-9,10-anthracenedione
NSC 646567
4,5-Dihydroxy-2-methylanthraquinone
2-Methyl-4,5-dihydroxyanthraquinone
3-Methyl-1,8-dihydroxyanthraquinone
C.I. 75400
CCRIS 3525
CHEBI:3687
Chrysophansaeure
UNII-N1ST8V8RR2
EINECS 207-572-2
N1ST8V8RR2
NSC-37132
NSC-646567
Anthraquinone, 1,8-dihydroxy-3-methyl-
DTXSID6024832
1,8-dihydroxy-3-methyl-9,10-anthraquinone
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl-
DTXCID704832
HSDB 8483
TURKEY-RHUBARB
RHENIC ACID
207-572-2
1,8-Dihydroxy-3-methylanthraquinone
Turkey rhubarb
1,8-dihydroxy-3-methylanthracene-9,10-dione
Crysophanic acid
Crysophanol
1,8-Dihydroxy-3-Methyl-Anthraquinone
MFCD00001208
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)
1,8-Dihydroxy-3-methylanthra-9,10-quinone
Chrysophanic acid (Chrysophanol)
NSC646567
Archinin
Rumicin
Spectrum_000792
Chrysophanol (Standard)
SpecPlus_000321
Spectrum2_000043
Spectrum3_001183
Spectrum4_001477
Spectrum5_000153
1,8-dihydroxy-3-methyl-anthracene-9,10-dione
BSPBio_002825
KBioGR_002053
KBioSS_001272
SPECTRUM300545
MLS000574888
CHEMBL41092
DivK1c_006417
SCHEMBL308131
SPBio_000165
CHRYSOPHANIC ACID [MI]
9, 1,8-dihydroxy-3-methyl-
Chrysophanol, analytical standard
KBio1_001361
KBio2_001272
KBio2_003840
KBio2_006408
KBio3_002325
HMS3656G17
CHRYSOPHANIC ACID [WHO-DD]
BCP23439
EX-A6777
NSC37132
Tox21_202499
Anthraquinone,8-dihydroxy-3-methyl-
BDBM50455992
CCG-38348
HY-13595R
LMPK13040006
MSK000528
S2406
STL564344
3-Methyl-1, 8-dihydroxyanthraquinone
4, 5-Dihydroxy-2-methylanthraquinone
AKOS015905000
AC-7980
BCP9000004
DS-9706
FC20424
SDCCGMLS-0066504.P001
NCGC00091823-01
NCGC00091823-02
NCGC00091823-03
NCGC00091823-04
NCGC00091823-05
NCGC00260048-01
CAS-481-74-3
HY-13595
SMR000156239
1,8-Dihydroxy-3-methylanthraquinone, 98%
8,9-dihydroxy-6-methyl-1,10-anthraquinone
C2505
NS00021170
SW219732-1
1,8-Dihydroxy-3-methylanthra-9,10-quinone #
EN300-7401332
SR-01000712223
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9CI
SR-01000712223-2
BRD-K59284035-001-02-0
BRD-K59284035-001-03-8
BRD-K59284035-001-07-9
Q15410875
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9CI)
1,8-DIHYDROXY-3-METHYL-9,10-DIHYDROANTHRACENE-9,10-DIONE
- Alemayehu G, Woldeyesus B, et al. (1997). (+)-Floribundone 3 from the pods of Senna septemtrionalis.. Bulletin of the Chemical Society of Ethiopia,1997,11(1),25-30. [View] [PubMed]
- Yenesew A, Ogur JA, et al. (1993). (R)-Prechrysophanol from Aloe graminicola.. Phytochemistry,1993,34(5),1442-1444. [View] [PubMed]
- Yenesew A, Wondimu A, et al. (1988). A comparative study of anthraquinones in rhizomes of Kniphofia species.. Biochemical systematics and ecology,1988,16(2),157-159. [View] [PubMed]
- Dagne E, Casser I, et al. (1992). Aloechrysone, a dihydroanthracenone from Aloe berhana.. Phytochemistry,1992,31(5),1791-1793. [View] [PubMed]
- Berhanu E, Fetene M, et al. (1986). Anthraquinones as taxonomic markers in Ethiopian Kniphofia species.. Phytochemistry,1986,25(4),847-850. [View] [PubMed]
- Rizk A, Hammouda F, et al. (1972). Anthraquinones of Asphodelus microcarpus. Phytochemistry, 1972, 11(6), 2122-2125. [View]
- Dagne E, Yenesew A, et al. (1994). Anthraquinones, pre-anthraquinones and isoeleutherol in the roots of Aloe species.. Phytochemistry,1994,35(2),401-406. [View] [PubMed]
- Wube AA, Bucar F, et al. (2005). Antimalarial compounds from Kniphofia foliosa roots.. Phytother Research,2005,19(6),472-476. [View] [PubMed]
- Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [View] [PubMed]
- Alemayehu G, Hailu A, et al. (1996). Bianthraquinones from Senna didymobotrya. Phytochemistry,1996,42(5),1423-1425. [View] [PubMed]
- Dagne E, Alemu M. (1991). Constituents of the leaves of four Aloe species from Ethiopia. Bulletin of the Chemical Society of Ethiopia,1991,5(2),87-91. [View] [PubMed]
- Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
- Midiwo JO, Rukunga GM. (1985). Distribution of anthraquinone pigments in Rumex species of Kenya.. Phytochemistry,1985,24(6),1390-1391. [View] [PubMed]
- Abegaz BM, Kebede T. (1995). Geshoidin: A bitter principle of Rhamnus prinoides and other constituents of the leaves. Bulletin of the Chemical Society of Ethiopia,1995,9(2),107-114. [View] [PubMed]
- Sema D, Lannang A, et al. (2022). In Vitro and in Vivo Evaluation of the Antimalarial Activities of Kniphofia reflexa Hutchinson ex Codd. Natural Product Communications, 2022, 17(10). [View]
- Munavu RM, Mudamba LO, et al. (1984). Isolation and Characterization of the Major Anthraquinone Pigments from Rumex abysinica.. Planta Medica,1984,50(1),111. [View] [PubMed]
- Dagne E, Steglich W. (1984). Knipholone: a unique anthraquinone derivative from Kniphofia foliosa.. Phytochemistry,1984,23(8),1729-1731. [View] [PubMed]
- Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
- ELhassan GOM, Adhikari A, et al. (2011). Phytochemical and biological studies on Aloe sinkatana Berger. The 14th NAPRECA Symposium and AAMPS Ethnoveterinary Medicine Symposium, At Nairobi, Kenya. August 2011. [View]
- Abdissa D, Geleta G, et al. (2017). Phytochemical investigation of Aloe pulcherrima roots and evaluation for its antibacterial and antiplasmodial activities.. PLoS One,2017,12(3):e0173882. [View] [PubMed]
- Bizuayehu Z, Ashebir F. (2012). Phytochemical investigation on the root of Rumex abyssinicus (Makmako). M.Sc. Thesis, Addis Ababa University, Ethiopia,2012. [View] [PubMed]
- Tsegaye G, Alemayehu G. (2006). Phytochemical investigation on the stem bark of Senna floribunda. M.Sc. Thesis, Addis Ababa University, Ethiopia,2006. [View] [PubMed]
- Alemayehu G, Abegaz B, et al. (1989). Quinones of Senna Didymobotrya.. Bulletin of the Chemical Society of Ethiopia,1989,3(1),37-40. [View] [PubMed]
- Dagne E. (1996). Review of the chemistry of Aloes of Africa. Bulletin of the Chemical Society of Ethiopia,1996,10(1),89-103. [View] [PubMed]
- Wanjohi JM, Yenesew A, et al. (2005). Three dimeric anthracene derivatives from the fruits of Bulbine abyssinica. Tetrahedron,2005,61(10),2667-2674. [View] [PubMed]
Pubchem:
10208
Cas:
481-74-3
Gnps:
CCMSLIB00000205162
Zinc:
ZINC000003861630
Kegg Ligand:
C10315
Chebi:
3687
Nmrshiftdb2:
60015815
Metabolights:
MTBLC3687
Chembl:
CHEMBL41092
Comptox:
DTXSID6024832
Bindingdb:
50455992
Selleck:
Chrysophanic-acid-Chrysophanol
CPRiL:
55915
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 254.24 g/mol
Anti-plasmodial
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.62
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.55
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.91
- Plasma Protein Binding
- 58.34
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.51
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 1.27
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.21
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.05
- 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
- 4.68
- Rat (Acute)
- 2.56
- Rat (Chronic Oral)
- 2.95
- Fathead Minnow
- 4.32
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 407.08
- Hydration Free Energy
- -8.83
- Log(D) at pH=7.4
- 2.54
- Log(P)
- 3.95
- Log S
- -5.66
- Log(Vapor Pressure)
- -7.6
- Melting Point
- 203.35
- pKa Acid
- 6.29
- pKa Basic
- 5.35
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9725 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.9725 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9492 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9492 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9388 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9388 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8962 |
| Fatty acid-binding protein, intestinal | P12104 | FABPI_HUMAN | Homo sapiens | 3 | 0.8962 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8852 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | F6MZ55 | F6MZ55_9FIRM | Sporomusa ovata | 3 | 0.8852 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8748 |
| E3 ubiquitin-protein ligase Mdm2 | P56273 | MDM2_XENLA | Xenopus laevis | 3 | 0.8748 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8725 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8725 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8576 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8576 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8471 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8471 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8445 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 4 | 0.8445 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8418 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8418 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8415 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8415 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8382 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 4 | 0.8382 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8340 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.8340 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.8326 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.8326 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.8325 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 4 | 0.8325 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.8158 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.8158 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8141 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.8141 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8109 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8109 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7976 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.7976 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 4 | 0.7902 |
| Biphenyl dioxygenase subunit alpha | P37333 | BPHA_PARXL | Paraburkholderia xenovorans | 4 | 0.7902 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7896 |
| Aklavinone 12-hydroxylase RdmE | Q54530 | DNRF_STREF | Streptomyces purpurascens | 4 | 0.7896 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7894 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7894 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7844 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7844 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7843 |
| Prostaglandin E synthase 2 | Q9N0A4 | PGES2_MACFA | Macaca fascicularis | 3 | 0.7843 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7840 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7840 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7780 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7780 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7739 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7739 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7714 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 3 | 0.7714 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7706 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7706 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7668 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7668 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7662 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7662 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7638 |
| Thiamine-phosphate synthase | P39594 | THIE_BACSU | Bacillus subtilis | 3 | 0.7638 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7542 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7542 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7538 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7538 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7532 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7532 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7497 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 2 | 0.7497 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7481 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7481 |
| Tyrosine-protein kinase Lyn | P25911 | LYN_MOUSE | Mus musculus | 3 | 0.7480 |
| Tyrosine-protein kinase Lyn | P25911 | LYN_MOUSE | Mus musculus | 3 | 0.7480 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7473 |
| Glycogen synthase | Q9V2J8 | Q9V2J8_PYRAB | Pyrococcus abyssi | 3 | 0.7473 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7449 |
| Carbonic anhydrase 12 | O43570 | CAH12_HUMAN | Homo sapiens | 2 | 0.7449 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7436 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7436 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7436 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7436 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7435 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7435 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7407 |
| Mitogen-activated protein kinase 10 | P53779 | MK10_HUMAN | Homo sapiens | 3 | 0.7407 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7379 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7379 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7375 |
| Fructose-1,6-bisphosphatase 1 | P00636 | F16P1_PIG | Sus scrofa | 3 | 0.7375 |
| Glutathione S-transferase A1 | P08263 | GSTA1_HUMAN | Homo sapiens | 2 | 0.7365 |
| Glutathione S-transferase A1 | P08263 | GSTA1_HUMAN | Homo sapiens | 2 | 0.7365 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7354 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7354 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7333 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7333 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7319 |
| E3 ubiquitin-protein ligase Mdm2 | Q00987 | MDM2_HUMAN | Homo sapiens | 3 | 0.7319 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7311 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.7311 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7298 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7298 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7285 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7285 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7282 |
| Scytalone dehydratase | P56221 | SCYD_MAGO7 | Pyricularia oryzae | 3 | 0.7282 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7278 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7278 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7278 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7278 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7267 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7267 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7252 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7252 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7241 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7241 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7222 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7222 |
| Protein S100-A4 | P26447 | S10A4_HUMAN | Homo sapiens | 3 | 0.7212 |
| Protein S100-A4 | P26447 | S10A4_HUMAN | Homo sapiens | 3 | 0.7212 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7210 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7210 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7206 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7206 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7202 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7202 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7188 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7188 |
| Proto-oncogene tyrosine-protein kinase receptor Ret | P07949 | RET_HUMAN | Homo sapiens | 3 | 0.7177 |
| Proto-oncogene tyrosine-protein kinase receptor Ret | P07949 | RET_HUMAN | Homo sapiens | 3 | 0.7177 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7161 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7161 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7153 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7153 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7140 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7140 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7127 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7127 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7125 |
| Pteridine reductase 1 | Q01782 | PTR1_LEIMA | Leishmania major | 3 | 0.7125 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7121 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7121 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7115 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7115 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7107 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7107 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7085 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7085 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7084 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 4 | 0.7084 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 4 | 0.7079 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 4 | 0.7079 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 3 | 0.7079 |
| Catalase-peroxidase | Q3JNW6 | KATG_BURP1 | Burkholderia pseudomallei | 3 | 0.7079 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7072 |
| Casein kinase I isoform delta | P48730 | KC1D_HUMAN | Homo sapiens | 3 | 0.7072 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7051 |
| Dihydrofolate reductase | Q83AB2 | Q83AB2_COXBU | Coxiella burnetii | 3 | 0.7051 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7045 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7045 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 4 | 0.7017 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 4 | 0.7017 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7013 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7013 |