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Luteolin hexoside

Family: Plantae - Arecaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glucoside

Canonical Smiles	OCC1OC(Oc2cc(O)cc3c2c(=O)cc(o3)c2ccc(c(c2)O)O)C(C(C1O)O)O
InChI	InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-15-5-9(23)4-14-17(15)12(26)6-13(30-14)8-1-2-10(24)11(25)3-8/h1-6,16,18-25,27-29H,7H2
InChIKey	KBGKQZVCLWKUDQ-UHFFFAOYSA-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	Syagrus romanzoffiana	Arecaceae	Plantae	290277

Showing of synonyms

El-Hawary S.S, Fathy F.I, et al. (2021). Anticholinesterase activity and metabolite profiling of Syagrus romanzoffiana (Cham.) Glassman leaves and fruits via UPLC–QTOF–PDA–MS. Natural product research, 2021, 35(10), 1671-1675. [View] [PubMed]

Pubchem: 15559460

Nmrshiftdb2: 60029435

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 448.38 g/mol

SMILES: O=c1ccoc(c12)cccc2OC3CCCCO3

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): -6.73
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.51
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 30.06
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: 14.85
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.66
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.89
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.2
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: -69.97
Rat (Acute): 2.39
Rat (Chronic Oral): 4.15
Fathead Minnow: 4.05
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: 623.76
Hydration Free Energy: -4.91
Log(D) at pH=7.4: 0.16
Log(P): -0.08
Log S: -3.82
Log(Vapor Pressure): -12.84
Melting Point: 240.34
pKa Acid: 4.89
pKa Basic: 7.54

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	0.9624
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9460
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9398
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9307
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9010
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8996
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8972
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8964
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8923
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8808
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8641
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8639
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8630
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8575
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8558
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8543
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8531
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8466
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8459
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8382
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8342
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8315
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8225
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8217
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8201
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8201
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8182
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8166
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8137
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8125
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8056
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8028
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.7970
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7941
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7931
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7911
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7788
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7782
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7706
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7705
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.7699
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7689
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7671
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7650
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7642
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7633
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7630
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7591
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7587
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7584
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7583
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7574
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7574
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7571
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7561
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7560
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7489
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7467
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7457
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7444
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7436
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7421
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	4	0.7410
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7381
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7366
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7354
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7347
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7318
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7308
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7307
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7304
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7286
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7277
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7277
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7276
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	4	0.7275
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7230
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7194
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7186
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7180
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	4	0.7179
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7137
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7136
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7121
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7120
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7116
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7108
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7092
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7090
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7086
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7082
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7080
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7063
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7051
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7049
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7042
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7038
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7038
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7025
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7023
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7021
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7015
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7013
Nucleoside diphosphate kinase B	P22392	NDKB_HUMAN	Homo sapiens	4	0.7009
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7008
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7007
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7007

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