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Luteolin-(6→8’’)-apigenin
- Family: Plantae - Anacardiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Biflavonoid
| Canonical Smiles | Oc1ccc(cc1)c1cc(=O)c2c(o1)c(c(cc2O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C30H18O11/c31-14-4-1-12(2-5-14)22-9-19(36)25-17(34)8-18(35)28(30(25)41-22)27-21(38)11-24-26(29(27)39)20(37)10-23(40-24)13-3-6-15(32)16(33)7-13/h1-11,31-35,38-39H |
| InChIKey | QBHMNRCKJJPDFY-UHFFFAOYSA-N |
| Formula | C30H18O11 |
| HBA | 11 |
| HBD | 7 |
| MW | 554.46 |
| Rotatable Bonds | 3 |
| TPSA | 202.03 |
| LogP | 4.84 |
| Number Rings | 6 |
| Number Aromatic Rings | 6 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.0 |
| Exact Mass | 554.08 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Schinus polygama | Anacardiaceae | Plantae | 2382318 |
Showing of synonyms
Luteolin-(6→8’’)-apigenin
No compound-protein relationship available.
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)-c(c4)ccc(c45)oc(cc5=O)-c6ccccc6
Level: 3
Mol. Weight: 554.46 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(ccc3)-c(c4)ccc(c45)occc5=O
Level: 2
Mol. Weight: 554.46 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)-c(c3)ccc(c34)oc(cc4=O)-c5ccccc5
Level: 2
Mol. Weight: 554.46 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)-c(c3)ccc(c34)occc4=O
Level: 1
Mol. Weight: 554.46 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 554.46 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 554.46 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 554.46 g/mol
Anti-inflammatory
Antidiabetic
Absorption
- Caco-2 (logPapp)
- -6.0
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.330
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 7.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.230
- Plasma Protein Binding
- 95.94
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- 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
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.890
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.200
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.430
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.710
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -8042.990
- Rat (Acute)
- 2.440
- Rat (Chronic Oral)
- 3.660
- Fathead Minnow
- 23.760
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 613.940
- Hydration Free Energy
- -3.110
- Log(D) at pH=7.4
- 3.080
- Log(P)
- 5.56
- Log S
- -6.52
- Log(Vapor Pressure)
- -10.07
- Melting Point
- 445.77
- pKa Acid
- 9.99
- pKa Basic
- 6.28
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.9632 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9631 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.9364 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9050 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8945 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 4 | 0.8750 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.8664 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8630 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.8606 |
| Metallo-beta-lactamase type 2 | P25910 | BLAB_BACFG | Bacteroides fragilis | 4 | 0.8526 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8507 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.8405 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8363 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 4 | 0.8354 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.8327 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8325 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8304 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8274 |
| Dihydroflavonol 4-reductase | P51110 | DFRA_VITVI | Vitis vinifera | 4 | 0.8272 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8202 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8027 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8012 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7987 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7976 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7934 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7906 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7885 |
| Succinyl-CoA:acetate CoA-transferase | B3EY95 | SCACT_ACEAC | Acetobacter aceti | 3 | 0.7871 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7820 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7806 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 4 | 0.7800 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 4 | 0.7709 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7708 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7697 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7647 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7623 |
| mRNA-capping enzyme subunit alpha | P78587 | MCE1_CANAX | Candida albicans | 3 | 0.7609 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.7570 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 3 | 0.7507 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.7504 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7477 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7447 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7441 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7420 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7403 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7390 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7374 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 4 | 0.7346 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7317 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7306 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7305 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7271 |
| Histone deacetylase 7 | Q8WUI4 | HDAC7_HUMAN | Homo sapiens | 3 | 0.7240 |
| Proto-oncogene tyrosine-protein kinase receptor Ret | P07949 | RET_HUMAN | Homo sapiens | 3 | 0.7230 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7193 |
| Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7159 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7143 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7140 |
| Ribosomal RNA large subunit methyltransferase J | P37634 | RLMJ_ECOLI | Escherichia coli | 4 | 0.7126 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7115 |
| Basic phospholipase A2 homolog piratoxin-1 | P58399 | PA2H1_BOTPI | Bothrops pirajai | 4 | 0.7099 |
| Caspase-6 | P55212 | CASP6_HUMAN | Homo sapiens | 3 | 0.7088 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7086 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7079 |
| 5-methylthioadenosine/S-adenosylhomocysteine deaminase | Q7NZ90 | Q7NZ90_CHRVO | Chromobacterium violaceum | 3 | 0.7051 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7046 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7044 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7039 |
| Methyltransferase | D0VX01 | D0VX01_WSLV | Wesselsbron virus | 4 | 0.7032 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7026 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7020 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7013 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7013 |
| Oxidized purine nucleoside triphosphate hydrolase | P36639 | 8ODP_HUMAN | Homo sapiens | 4 | 0.7009 |