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Luteolin 7-O-glucopyranoside

Family: Plantae - Dipsacaceae
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
InChI	InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16?,18-,19+,20?,21-/m1/s1
InChIKey	PEFNSGRTCBGNAN-NFRVFMFJSA-N
Formula	C₂₁H₂₀O₁₁
HBA	11
HBD	7
MW	448.38
Rotatable Bonds	4
TPSA	190.28
LogP	-0.24
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	448.1
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scabiosa atropurpurea	Dipsacaceae	Plantae	242170

Showing of synonyms

Besbes Hlila M, Mosbah H, et al. (2016). Antimicrobial activity of Scabiosa arenaria Forssk. extracts and pure compounds using bioguided fractionation. Chemistry & biodiversity, 2016, 13(10), 1262-1272. [View] [PubMed]

Pubchem: 44258066

Gnps: CCMSLIB00006126954

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 448.38 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 448.38 g/mol

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

Level: 1

Mol. Weight: 448.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 448.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.47
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.86
Plasma Protein Binding: 76.12
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: 14.32
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.75
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.97
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.21
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: -72.86
Rat (Acute): 2.37
Rat (Chronic Oral): 4.06
Fathead Minnow: 4.02
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 613.51
Hydration Free Energy: -4.73
Log(D) at pH=7.4: 0.41
Log(P): 0.37
Log S: -4.08
Log(Vapor Pressure): -13.16
Melting Point: 233.04
pKa Acid: 5.13
pKa Basic: 7.4

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	0.9628
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9382
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9340
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9149
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9002
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.9000
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8960
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8929
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8899
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8742
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8690
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8662
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8649
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8637
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8617
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8616
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8594
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8550
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8536
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8367
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8354
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8338
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8288
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8279
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8264
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8263
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8251
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.8228
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8205
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8205
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8169
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8153
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8071
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.8060
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8050
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8047
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8033
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8019
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.8005
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.8003
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7987
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7906
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7878
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7872
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7820
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7819
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7773
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7773
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7741
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7738
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7724
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7723
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7717
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.7716
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7694
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7667
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7617
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7609
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7591
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7588
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7530
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7529
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7525
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7517
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7514
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	4	0.7514
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7496
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7469
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7446
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7442
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7435
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7415
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7407
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7406
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7355
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7328
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7326
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7324
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7323
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7313
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7310
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7310
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7302
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7302
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7284
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7277
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7277
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7265
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7250
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7247
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7236
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7216
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7212
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7210
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7207
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.7201
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7195
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7189
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7188
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7180
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7170
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7156
Replicase polyprotein 1ab	P0C6X7	R1AB_CVHSA	Human SARS coronavirus	4	0.7153
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7139
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7137
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7136
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7133
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7131
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7126
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7120
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7119
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7115
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7114
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7113
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7113
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7107
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7107
DNA-(apurinic or apyrimidinic site) lyase	Q97FM4	Q97FM4_CLOAB	Clostridium acetobutylicum	4	0.7100
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7096
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7091
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7090
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7090
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7075
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7074
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7068
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7066
Histone-arginine methyltransferase CARM1	Q4AE70	CARM1_RAT	Rattus norvegicus	4	0.7065
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7064
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7056
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7043
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7039
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7030
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7016
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7016
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7015
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7006
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7004
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7003

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