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Luteolin 7-[6′′′-acetylallosyl-(1→2)glucoside]
- Family: Lamiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone Glycoside
| Canonical Smiles | OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(COC(=O)C)[C@H]([C@@H](C1O)O)O |
|---|---|
| InChI | InChI=1S/C29H32O17/c1-10(31)41-9-20-23(37)24(38)26(40)28(45-20)46-27-25(39)22(36)19(8-30)44-29(27)42-12-5-15(34)21-16(35)7-17(43-18(21)6-12)11-2-3-13(32)14(33)4-11/h2-7,19-20,22-30,32-34,36-40H,8-9H2,1H3/t19?,20?,22-,23-,24+,25+,26?,27?,28+,29-/m1/s1 |
| InChIKey | SDLRUUXTNVUGJL-WJBWUEBSSA-N |
| Formula | C29H32O17 |
| HBA | 17 |
| HBD | 9 |
| MW | 652.56 |
| Rotatable Bonds | 8 |
| TPSA | 275.5 |
| LogP | -1.85 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 46 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.45 |
| Exact Mass | 652.16 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Stachys aegyptiaca | Lamiaceae | Plantae | 1391947 |
Showing of synonyms
Luteolin 7-[6′′′-acetylallosyl-(1→2)glucoside]
Luteolin 7-(6'''-acetylallosyl-(1->2)-glucoside)
LMPK12110692
- El-Ansari M, Abdalla M, et al. (1991). Flavonoid constituents of Stachys aegyptiaca. Phytochemistry, 1991,30(4),1169-1173. [View]
Pubchem:
44258116
No compound-protein relationship available.
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5
Level: 3
Mol. Weight: 422.48 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4
Level: 2
Mol. Weight: 346.38 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 322.36 g/mol
SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 246.26 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 222.24 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 186.25 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 146.14 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 86.13 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.65
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 32.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.8
- Plasma Protein Binding
- 48.05
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-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
- 10.9
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.41
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.92
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.83
- Micronucleos
- Toxic
- NR-AhR
- Safe
- 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
- -55925.51
- Rat (Acute)
- 2.21
- Rat (Chronic Oral)
- 4.05
- Fathead Minnow
- 89.0
- 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
- 695.93
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -0.21
- Log(P)
- -0.33
- Log S
- -4.94
- Log(Vapor Pressure)
- -51.92
- Melting Point
- 212.58
- pKa Acid
- 4.22
- pKa Basic
- 6.14
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9387 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9048 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.8870 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8865 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.8835 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8777 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8766 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.8761 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 4 | 0.8682 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8625 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8559 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.8506 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8430 |
| Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase | Q46381 | BPHB_COMTE | Comamonas testosteroni | 3 | 0.8382 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8357 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8356 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8308 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8299 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8268 |
| GTP 3',8-cyclase | P69848 | MOAA_STAA8 | Staphylococcus aureus | 4 | 0.8180 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8179 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8164 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8143 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 5 | 0.8040 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 3 | 0.7999 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7919 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7917 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7854 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7758 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7749 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7738 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7702 |
| Serine/threonine-protein kinase toxin HipA | P23874 | HIPA_ECOLI | Escherichia coli | 3 | 0.7700 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7699 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7695 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7679 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7678 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7663 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7663 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 4 | 0.7633 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 4 | 0.7623 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7623 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 4 | 0.7602 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7601 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7568 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 4 | 0.7495 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.7494 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7483 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7482 |
| Mitogen-activated protein kinase kinase kinase 5 | Q99683 | M3K5_HUMAN | Homo sapiens | 3 | 0.7474 |
| Cytosine-specific methyltransferase | Q8EVR5 | Q8EVR5_MYCPE | Mycoplasma penetrans | 4 | 0.7473 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7452 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7447 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7443 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7427 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.7400 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7393 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7359 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7347 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7344 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7309 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7298 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7297 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7285 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7263 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7259 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7243 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7232 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7219 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7215 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7172 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.7159 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 4 | 0.7153 |
| Histone deacetylase 7 | Q8WUI4 | HDAC7_HUMAN | Homo sapiens | 3 | 0.7150 |
| Peripheral plasma membrane protein CASK | O14936 | CSKP_HUMAN | Homo sapiens | 3 | 0.7141 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 3 | 0.7129 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7108 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7106 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7101 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.7099 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7098 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7095 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7084 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7079 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7075 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7074 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 3 | 0.7066 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7066 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7043 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7043 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7042 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7040 |
| Type II methyltransferase M.TaqI | P14385 | MTTA_THEAQ | Thermus aquaticus | 3 | 0.7034 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 3 | 0.7029 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7023 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7017 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7013 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7010 |
| NADPH--cytochrome P450 reductase | P00388 | NCPR_RAT | Rattus norvegicus | 4 | 0.7002 |
| Genome polyprotein | P12823 | POLG_DEN2P | Dengue virus type 2 | 3 | 0.7001 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 3 | 0.7001 |