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Luteolin-6,8-di-C-alpha-L-arabinopyranoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	O[C@H]1[C@@H](O)CO[C@@H]([C@@H]1O)c1c(O)c([C@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(c(c1)O)O)O
InChI	InChI=1S/C25H26O14/c26-8-2-1-7(3-9(8)27)13-4-10(28)14-19(33)15(24-21(35)17(31)11(29)5-37-24)20(34)16(23(14)39-13)25-22(36)18(32)12(30)6-38-25/h1-4,11-12,17-18,21-22,24-27,29-36H,5-6H2/t11-,12-,17-,18-,21+,22+,24+,25+/m0/s1
InChIKey	ROOCIIPDYQXZNW-BEOWTOLDSA-N
Formula	C₂₅H₂₆O₁₄
HBA	14
HBD	10
MW	550.47
Rotatable Bonds	3
TPSA	250.97
LogP	-1.41
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	550.13
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Premna odorata	Lamiaceae	Plantae	1037421

Showing of synonyms

Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5

Level: 3

Mol. Weight: 550.47 g/mol

SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4

Level: 2

Mol. Weight: 550.47 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 550.47 g/mol

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 550.47 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 550.47 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 550.47 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 550.47 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 550.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 550.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 550.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.52
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.34
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.61
Plasma Protein Binding: 68.89
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: 11.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.4
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.75
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.51
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: -2211.28
Rat (Acute): 2.39
Rat (Chronic Oral): 4.87
Fathead Minnow: 4.93
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: 721.15
Hydration Free Energy: -3.2
Log(D) at pH=7.4: -1.32
Log(P): -0.46
Log S: -3.73
Log(Vapor Pressure): -14.05
Melting Point: 226.79
pKa Acid: 2.65
pKa Basic: 10.36

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	0.9575
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8845
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8644
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8571
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8523
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8312
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8301
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8221
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8197
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8097
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8093
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.8042
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8021
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7997
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7882
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7740
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7675
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7638
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7633
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7596
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7508
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7478
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7434
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7338
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7315
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7310
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7301
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7258
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7212
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7188
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7158
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7129
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7109
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7076
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7068
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7067
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7045
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7036
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7028
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7014

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