| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 3rd, 2008 | 21 | No |
Popular Name: Luteolin Luteolin
Find On: PubMed — Wikipedia — Google
CAS Numbers: 491-70-3 , [491-70-3]
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-one
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-chromenone
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-olate luteolin-7-olate(1-)
3',4',5,7-Tetrahydroxyflavone, 97%
3',4',5,7-Tetrahydroxyflavone, Luteoline, Luteolol
3',4',5,7-Tetrahydroxyflavone; 491-70-3; 5,7,3',4'-Tetrahydroxyflavone; C01514; Luteolin
491-70-3; Luteolin; Prestwick_122
CHEBI:12082; CHEBI:14536; CHEBI:6578; CHEBI:25086
DIHYDROXYPHENYLDIHYDROXYCHROMENON
Leteolin with HPLC [491-70-3]; (5,7,3',4'-Tetrahydroxyflavone)
Luteolin Monohydrate [491-70-3]; (3',4',5,7-Tetrahydroxyflavone)
LUTEOLIN MONOHYDRATE; [491-70-3]
Luteolin [491-70-3]; (5,7,3',4'-Tetrahydroxyflavone)
Luteolin-4'-O-glucoside [6920-38-3]
Luteolin-7,3'-di-O-glucoside with HPLC [52187-80-1]
Luteolin-7-O-Glucoside [5373-11-5]; (Cynaroside)
Luteolin-7-O-glucoside, >90% [5373-11-5]
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | 1.97 | -0.94 | -14.61 | 4 | 6 | 0 | 111 | 286.239 | 1 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| biological_source | Occurs in many plants in Leguminosae, Resedaceae, Euphorbiaceae, Umbelliferae, Scrophulariaceae, Fabaceae, Asteraceae, Cistaceae, Passifloraceae, Yerbenaceae and Hepaticae. First | ZereneX Building Blocks |
| M.P. | 210 C (dec.) | Indofine |
| MP | 210o C | Indofine |
| M.P. | 220-250 C | Indofine |
| MP | 220-250o C | Indofine |
| MP | 241-249o C | Indofine |
| MP | 328-330o C | Indofine |
| MP | 330 | TCI |
| Purity | 95% | Fluorochem |
| Purity | 95+% | Matrix Scientific |
| Purity | 97% | Fluorochem |
| Purity | 98% | APIChem |
| M.P. | >300 C | Indofine |
| Melting_Point | >300? | Alfa-Aesar |
| MP | >300o C | Indofine |
| Melting_Point | >300° | Alfa-Aesar |
| UniProt Database Links | AB5C_ARATH; FABI_ECOLI; FOMT1_WHEAT; FOMT2_WHEAT; GBA3_HUMAN; NODM_RHIML; OMT15_ORYSJ; OMT17_ORYSJ; OMT1_CHRAE; OMT1_ORYSJ; OMT2_CHRAE; U73B2_ARATH; UBGAT_SCUBA | ChEBI |
| biological_use | Antiinflammatory | IBScreen Bioactives IBScreen Bioactives |
| Indications | antioxidant, anti-inflammatory | KeyOrganics Bioactives |
| biological_use | Antispasmodic | IBScreen Bioactives |
| biological_use | Antitumourigenic activity in mice reported | IBScreen Bioactives |
| biological_use | Antitussive agent | IBScreen Bioactives |
| Patent Database Links | EP1600061; EP1808169; EP1808172; EP1925311; EP1932517; US2007184133; US2007191330; US2007202195; US2007212395; US2007224296; WO2005020981; WO2007098873; WO2007103555; WO2007130777; WO2007130882; WO2007131767 | ChEBI |
| Warnings | IRRITANT | Matrix Scientific |
| APPEARANCE | Light yellow needles | Indofine |
| mechanism | Lipid peroxidation inhibitor in rat liver microsomes | IBScreen Bioactives |
| Target | Lipoprotein lipase(P06858)&Tyrosyl-DNA phosphodiesterase 1(Q9NUW8)&Nitric oxide synthase, inducible(P35228)&Trypsin-1(P07477)&Cholecystokinin(P06307)&Cbp/p300-interacting transactivator 1(Q99966)&Peroxisome proliferator-activated receptor alpha(Q07869)&Fa | Herbal Ingredients Targets |
| Target | PDE | Selleck Chemicals |
| biological_use | Shows anti-HIV activity | IBScreen Bioactives |
| SOLUBILITY | Soluble in 5 mg/20 ml in methanol | Indofine |
| SOLUBILITY | Soluble in Ethyl acetate:Formic acid:; Acetic acid (100:11:11) | Indofine |
| SOLUBILITY | Soluble in Ethyl acetate:formic acid:acetic acid (100:11:11) | Indofine |
| SOLUBILITY | Soluble in Methanol | Indofine |
| APPEARANCE | Yellow powder | Indofine |
| M.P. | ~241-249 C | Indofine |
| M.P. | ~328-330 C | Indofine |
| MP | ~330 °C(lit.) | Indofine |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| FABI-1-B | Enoyl-[acyl-carrier-protein] Reductase (cluster #1 Of 2), Bacterial | Bacteria | 7050 | 0.34 | Binding ≤ 10μM |
| NANH-1-B | Sialidase (cluster #1 Of 1), Bacterial | Bacteria | 4300 | 0.36 | Binding ≤ 10μM |
| AA1R-2-E | Adenosine A1 Receptor (cluster #2 Of 4), Eukaryotic | Eukaryotes | 1660 | 0.39 | Binding ≤ 10μM |
| ABCG2-1-E | ATP-binding Cassette Sub-family G Member 2 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 8900 | 0.34 | Binding ≤ 10μM |
| ALDR-1-E | Aldose Reductase (cluster #1 Of 5), Eukaryotic | Eukaryotes | 9570 | 0.33 | Binding ≤ 10μM |
| AOFA-4-E | Monoamine Oxidase A (cluster #4 Of 8), Eukaryotic | Eukaryotes | 4900 | 0.35 | Binding ≤ 10μM |
| CCNB1-1-E | G2/mitotic-specific Cyclin B1 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 6200 | 0.35 | Binding ≤ 10μM |
| CCNB2-1-E | G2/mitotic-specific Cyclin B2 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 6200 | 0.35 | Binding ≤ 10μM |
| CCNB3-1-E | G2/mitotic-specific Cyclin B3 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 6200 | 0.35 | Binding ≤ 10μM |
| CD38-1-E | Lymphocyte Differentiation Antigen CD38 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 8200 | 0.34 | Binding ≤ 10μM |
| CDK1-1-E | Cyclin-dependent Kinase 1 (cluster #1 Of 4), Eukaryotic | Eukaryotes | 6200 | 0.35 | Binding ≤ 10μM |
| CP1B1-1-E | Cytochrome P450 1B1 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 79 | 0.47 | Binding ≤ 10μM |
| GSK3A-1-E | Glycogen Synthase Kinase-3 Alpha (cluster #1 Of 3), Eukaryotic | Eukaryotes | 800 | 0.41 | Binding ≤ 10μM |
| GSK3B-7-E | Glycogen Synthase Kinase-3 Beta (cluster #7 Of 7), Eukaryotic | Eukaryotes | 800 | 0.41 | Binding ≤ 10μM |
| LGUL-2-E | Glyoxalase I (cluster #2 Of 2), Eukaryotic | Eukaryotes | 7700 | 0.34 | Binding ≤ 10μM |
| LOX1-1-E | Seed Lipoxygenase-1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 3200 | 0.37 | Binding ≤ 10μM |
| NOX4-1-E | NADPH Oxidase 4 (cluster #1 Of 1), Eukaryotic | Eukaryotes | 850 | 0.40 | Binding ≤ 10μM |
| Q965D5-1-E | Enoyl-acyl-carrier Protein Reductase (cluster #1 Of 1), Eukaryotic | Eukaryotes | 2100 | 0.38 | Binding ≤ 10μM |
| Q965D6-1-E | 3-oxoacyl-acyl-carrier Protein Reductase (cluster #1 Of 2), Eukaryotic | Eukaryotes | 800 | 0.41 | Binding ≤ 10μM |
| Q965D7-2-E | Fatty Acid Synthase (cluster #2 Of 2), Eukaryotic | Eukaryotes | 5000 | 0.35 | Binding ≤ 10μM |
| TOP1-1-E | DNA Topoisomerase 1 (cluster #1 Of 2), Eukaryotic | Eukaryotes | 660 | 0.41 | Binding ≤ 10μM |
| XDH-2-E | Xanthine Dehydrogenase (cluster #2 Of 2), Eukaryotic | Eukaryotes | 1900 | 0.38 | Binding ≤ 10μM |
| SC6A3-1-E | Dopamine Transporter (cluster #1 Of 1), Eukaryotic | Eukaryotes | 1450 | 0.39 | Functional ≤ 10μM |
| CP1A1-1-E | Cytochrome P450 1A1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 890 | 0.40 | ADME/T ≤ 10μM |
| CP1A2-1-E | Cytochrome P450 1A2 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 3370 | 0.36 | ADME/T ≤ 10μM |
| CP1B1-1-E | Cytochrome P450 1B1 (cluster #1 Of 3), Eukaryotic | Eukaryotes | 56 | 0.48 | ADME/T ≤ 10μM |
| Z104294-2-O | Cyclin-dependent Kinase 5/CDK5 Activator 1 (cluster #2 Of 2), Other | Other | 3800 | 0.36 | Binding ≤ 10μM |
| Z50425-11-O | Plasmodium Falciparum (cluster #11 Of 22), Other | Other | 9600 | 0.33 | Functional ≤ 10μM |
| Z50607-4-O | Human Immunodeficiency Virus 1 (cluster #4 Of 10), Other | Other | 10000 | 0.33 | Functional ≤ 10μM |
| Z50652-3-O | Influenza A Virus (cluster #3 Of 4), Other | Other | 6820 | 0.34 | Functional ≤ 10μM |
| Z80150-2-O | H9c2 (Cardiomyoblast Cells) (cluster #2 Of 2), Other | Other | 5530 | 0.35 | Functional ≤ 10μM |
| Z80418-2-O | RAW264.7 (Monocytic-macrophage Leukemia Cells) (cluster #2 Of 9), Other | Other | 7500 | 0.34 | Functional ≤ 10μM |
| Z80420-1-O | RBL-2H3 (Basophilic Leukemia Cells) (cluster #1 Of 2), Other | Other | 5800 | 0.35 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| Q965D6_PLAFA | Q965D6 | 3-oxoacyl-acyl-carrier Protein Reductase, Plafa | 800 | 0.41 | Binding ≤ 1μM |
| CP1B1_HUMAN | Q16678 | Cytochrome P450 1B1, Human | 79 | 0.47 | Binding ≤ 1μM |
| TOP1_RAT | Q9WUL0 | DNA Topoisomerase 1, Rat | 660 | 0.41 | Binding ≤ 1μM |
| GSK3A_HUMAN | P49840 | Glycogen Synthase Kinase-3 Alpha, Human | 800 | 0.41 | Binding ≤ 1μM |
| GSK3B_HUMAN | P49841 | Glycogen Synthase Kinase-3 Beta, Human | 800 | 0.41 | Binding ≤ 1μM |
| NOX4_HUMAN | Q9NPH5 | NADPH Oxidase 4, Human | 850 | 0.40 | Binding ≤ 1μM |
| XDH_HUMAN | P47989 | Xanthine Dehydrogenase, Human | 550 | 0.42 | Binding ≤ 1μM |
| Q965D6_PLAFA | Q965D6 | 3-oxoacyl-acyl-carrier Protein Reductase, Plafa | 1800 | 0.38 | Binding ≤ 10μM |
| AA1R_RAT | P25099 | Adenosine A1 Receptor, Rat | 1550 | 0.39 | Binding ≤ 10μM |
| ALDR_RAT | P07943 | Aldose Reductase, Rat | 1540 | 0.39 | Binding ≤ 10μM |
| ALDR_BOVIN | P16116 | Aldose Reductase, Bovin | 9570 | 0.33 | Binding ≤ 10μM |
| ABCG2_HUMAN | Q9UNQ0 | ATP-binding Cassette Sub-family G Member 2, Human | 8900 | 0.34 | Binding ≤ 10μM |
| CDK1_HUMAN | P06493 | Cyclin-dependent Kinase 1, Human | 6200 | 0.35 | Binding ≤ 10μM |
| Z104294 | Z104294 | Cyclin-dependent Kinase 5/CDK5 Activator 1 | 3800 | 0.36 | Binding ≤ 10μM |
| CP1B1_HUMAN | Q16678 | Cytochrome P450 1B1, Human | 79 | 0.47 | Binding ≤ 10μM |
| TOP1_RAT | Q9WUL0 | DNA Topoisomerase 1, Rat | 5000 | 0.35 | Binding ≤ 10μM |
| Q965D5_PLAFA | Q965D5 | Enoyl-acyl-carrier Protein Reductase, Plafa | 2000 | 0.38 | Binding ≤ 10μM |
| FABI_ECOLI | P0AEK4 | Enoyl-[acyl-carrier-protein] Reductase, Ecoli | 7050 | 0.34 | Binding ≤ 10μM |
| Q965D7_PLAFA | Q965D7 | Fatty Acid Synthase, Plafa | 5000 | 0.35 | Binding ≤ 10μM |
| CCNB1_HUMAN | P14635 | G2/mitotic-specific Cyclin B1, Human | 6200 | 0.35 | Binding ≤ 10μM |
| CCNB2_HUMAN | O95067 | G2/mitotic-specific Cyclin B2, Human | 6200 | 0.35 | Binding ≤ 10μM |
| CCNB3_HUMAN | Q8WWL7 | G2/mitotic-specific Cyclin B3, Human | 6200 | 0.35 | Binding ≤ 10μM |
| GSK3A_HUMAN | P49840 | Glycogen Synthase Kinase-3 Alpha, Human | 800 | 0.41 | Binding ≤ 10μM |
| GSK3B_HUMAN | P49841 | Glycogen Synthase Kinase-3 Beta, Human | 800 | 0.41 | Binding ≤ 10μM |
| LGUL_HUMAN | Q04760 | Glyoxalase I, Human | 7700 | 0.34 | Binding ≤ 10μM |
| CD38_HUMAN | P28907 | Lymphocyte Differentiation Antigen CD38, Human | 8200 | 0.34 | Binding ≤ 10μM |
| AOFA_HUMAN | P21397 | Monoamine Oxidase A, Human | 4900 | 0.35 | Binding ≤ 10μM |
| NOX4_HUMAN | Q9NPH5 | NADPH Oxidase 4, Human | 850 | 0.40 | Binding ≤ 10μM |
| LOX1_SOYBN | P08170 | Seed Lipoxygenase-1, Soybn | 3200 | 0.37 | Binding ≤ 10μM |
| NANH_CLOPE | P10481 | Sialidase, Clope | 4300 | 0.36 | Binding ≤ 10μM |
| XDH_BOVIN | P80457 | Xanthine Dehydrogenase, Bovin | 1900 | 0.38 | Binding ≤ 10μM |
| XDH_HUMAN | P47989 | Xanthine Dehydrogenase, Human | 550 | 0.42 | Binding ≤ 10μM |
| SC6A3_RAT | P23977 | Dopamine Transporter, Rat | 1450 | 0.39 | Functional ≤ 10μM |
| Z80150 | Z80150 | H9c2 (Cardiomyoblast Cells) | 5530 | 0.35 | Functional ≤ 10μM |
| Z50607 | Z50607 | Human Immunodeficiency Virus 1 | 10000 | 0.33 | Functional ≤ 10μM |
| Z50652 | Z50652 | Influenza A Virus | 6820 | 0.34 | Functional ≤ 10μM |
| Z50425 | Z50425 | Plasmodium Falciparum | 9600 | 0.33 | Functional ≤ 10μM |
| Z80418 | Z80418 | RAW264.7 (Monocytic-macrophage Leukemia Cells) | 7390 | 0.34 | Functional ≤ 10μM |
| Z80420 | Z80420 | RBL-2H3 (Basophilic Leukemia Cells) | 3700 | 0.36 | Functional ≤ 10μM |
| CP1A1_HUMAN | P04798 | Cytochrome P450 1A1, Human | 1249 | 0.39 | ADME/T ≤ 10μM |
| CP1A2_HUMAN | P05177 | Cytochrome P450 1A2, Human | 3370 | 0.36 | ADME/T ≤ 10μM |
| CP1B1_HUMAN | Q16678 | Cytochrome P450 1B1, Human | 56 | 0.48 | ADME/T ≤ 10μM |
| Description | Species |
|---|---|
| Abacavir transmembrane transport | |
| Activation of NIMA Kinases NEK9, NEK6, NEK7 | |
| Adenosine P1 receptors | |
| Aflatoxin activation and detoxification | |
| AKT phosphorylates targets in the cytosol | |
| APC truncation mutants have impaired AXIN binding | |
| APC/C:Cdc20 mediated degradation of Cyclin B | |
| Aromatic amines can be N-hydroxylated or N-dealkylated by CYP1A2 | |
| AXIN missense mutants destabilize the destruction complex | |
| Beta-catenin phosphorylation cascade | |
| Chk1/Chk2(Cds1) mediated inactivation of Cyclin B:Cdk1 complex | |
| Condensation of Prometaphase Chromosomes | |
| Condensation of Prophase Chromosomes | |
| Constitutive PI3K/AKT Signaling in Cancer | |
| CRMPs in Sema3A signaling | |
| Cyclin A/B1 associated events during G2/M transition | |
| Cyclin B2 mediated events | |
| Degradation of beta-catenin by the destruction complex | |
| Depolymerisation of the Nuclear Lamina | |
| disassembly of the destruction complex and recruitment of AXIN to the membrane | |
| Dopamine clearance from the synaptic cleft | |
| E2F mediated regulation of DNA replication | |
| E2F-enabled inhibition of pre-replication complex formation | |
| Endogenous sterols | |
| Enzymatic degradation of dopamine by COMT | |
| Enzymatic degradation of Dopamine by monoamine oxidase | |
| ERK1 activation | |
| G alpha (i) signalling events | |
| G0 and Early G1 | |
| G1/S-Specific Transcription | |
| G2/M DNA replication checkpoint | |
| Golgi Cisternae Pericentriolar Stack Reorganization | |
| Iron uptake and transport | |
| Loss of Nlp from mitotic centrosomes | |
| Loss of proteins required for interphase microtubule organization from the ce | |
| MASTL Facilitates Mitotic Progression | |
| Metabolism of serotonin | |
| Methylation | |
| misspliced GSK3beta mutants stabilize beta-catenin | |
| Monoamines are oxidized to aldehydes by MAOA and MAOB, producing NH3 and H2O2 | |
| Na+/Cl- dependent neurotransmitter transporters | |
| Norepinephrine Neurotransmitter Release Cycle | |
| Nuclear Pore Complex (NPC) Disassembly | |
| Phosphorylation of Emi1 | |
| Phosphorylation of proteins involved in the G2/M transition by Cyclin A:Cdc2 com | |
| Phosphorylation of the APC/C | |
| Polo-like kinase mediated events | |
| PPARA activates gene expression | |
| Pregnenolone biosynthesis | |
| Purine catabolism | |
| Recruitment of mitotic centrosome proteins and complexes | |
| Recruitment of NuMA to mitotic centrosomes | |
| Regulation of APC/C activators between G1/S and early anaphase | |
| Regulation of HSF1-mediated heat shock response | |
| Regulation of PLK1 Activity at G2/M Transition | |
| Resolution of Sister Chromatid Cohesion | |
| S33 mutants of beta-catenin aren't phosphorylated | |
| S37 mutants of beta-catenin aren't phosphorylated | |
| S45 mutants of beta-catenin aren't phosphorylated | |
| Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) | |
| Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET) | |
| T41 mutants of beta-catenin aren't phosphorylated | |
| truncations of AMER1 destabilize the destruction complex | |
| XBP1(S) activates chaperone genes | |
| Xenobiotics |
