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6,8-di-C-glucosylluteolin
- Family: Plantae - Labiateae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone Glycoside
| Canonical Smiles | C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O)O |
|---|---|
| InChI | InChI=1S/C27H30O16/c28-5-12-17(33)21(37)23(39)26(42-12)15-19(35)14-10(32)4-11(7-1-2-8(30)9(31)3-7)41-25(14)16(20(15)36)27-24(40)22(38)18(34)13(6-29)43-27/h1-4,12-13,17-18,21-24,26-31,33-40H,5-6H2 |
| InChIKey | ZLPSOQFIIQIIAX-UHFFFAOYSA-N |
| Formula | C27H30O16 |
| HBA | 16 |
| HBD | 12 |
| MW | 610.52 |
| Rotatable Bonds | 5 |
| TPSA | 291.43 |
| LogP | -2.69 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.44 |
| Exact Mass | 610.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Phlomis aurea | Labiateae | Plantae | 997702 |
Showing of synonyms
6,8-di-C-glucosylluteolin
Luteolin 6-C-glucoside 8-C-arabinoside
NP-006989(12)
Compound NP-006989
SCHEMBL416266
AKOS040739556
- El-Negoumy S, Abdalla M, et al. (1986). Flavonoids of Phlomis Aurea and P. Floccosa. Phytochemistry, 1986, 25(3), 772-774.. [View]
Pubchem:
3549960
No compound-protein relationship available.
SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5
Level: 3
Mol. Weight: 610.52 g/mol
SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4
Level: 2
Mol. Weight: 610.52 g/mol
SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 610.52 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 610.52 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 610.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.39
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -6.42
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 12.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.49
- Plasma Protein Binding
- -13.01
- 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
- 8.68
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -4.49
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.77
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.61
- 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
- -13848.74
- Rat (Acute)
- 2.37
- Rat (Chronic Oral)
- 5.07
- Fathead Minnow
- 27.8
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 573.96
- Hydration Free Energy
- -3.13
- Log(D) at pH=7.4
- -2.58
- Log(P)
- -0.85
- Log S
- -3.18
- Log(Vapor Pressure)
- -15.93
- Melting Point
- 208.77
- pKa Acid
- 0.7
- pKa Basic
- 12.64
| 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 | 0.9325 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8828 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8656 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8534 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8427 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8303 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8198 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7971 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7965 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.7818 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.7806 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7799 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7653 |
| Beta sliding clamp | P0A988 | DPO3B_ECOLI | Escherichia coli | 3 | 0.7649 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7559 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7498 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7449 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 3 | 0.7431 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7408 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7407 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7384 |
| Neopullulanase 2 | Q08751 | NEPU2_THEVU | Thermoactinomyces vulgaris | 3 | 0.7323 |
| Primosomal protein N' | A6TGC5 | A6TGC5_KLEP7 | Klebsiella pneumoniae subsp. pneumoniae | 4 | 0.7265 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.7249 |
| Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 | Q9Y3Q4 | HCN4_HUMAN | Homo sapiens | 4 | 0.7219 |
| Ribosomal RNA large subunit methyltransferase J | P37634 | RLMJ_ECOLI | Escherichia coli | 4 | 0.7141 |
| DNA polymerase theta | O75417 | DPOLQ_HUMAN | Homo sapiens | 4 | 0.7064 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 3 | 0.7058 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7048 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7032 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7016 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7012 |