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Luteolin glucoside

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

Canonical Smiles	OC[C@H]1OC(Oc2cc(O)cc3c2c(=O)cc(o3)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)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/t16-,18-,19+,20-,21?/m1/s1
InChIKey	KBGKQZVCLWKUDQ-MKJMBMEGSA-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	Potamogeton perfoliatus	Potamogetonaceae	Plantae	55320

Showing of synonyms

Rezq S, Mahmoud M.F, et al. (2021). Anti-Inflammatory, Antipyretic, and Analgesic Properties of Potamogeton perfoliatus Extract: In Vitro and In Vivo Study. Molecules, 2021, 26(16), 4826. [View] [PubMed]

Pubchem: 15559461

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: 0.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.83
Plasma Protein Binding: 78.21
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: 14.86
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.97
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: 5.19
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: -72.72
Rat (Acute): 2.4
Rat (Chronic Oral): 4.14
Fathead Minnow: 3.98
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: 628.15
Hydration Free Energy: -4.9
Log(D) at pH=7.4: 0.27
Log(P): -0.22
Log S: -3.89
Log(Vapor Pressure): -13.56
Melting Point: 241.62
pKa Acid: 4.89
pKa Basic: 7.6

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	0.9626
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9401
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9304
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9048
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8996
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8980
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8959
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8927
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.8841
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8648
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8648
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8488
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8485
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8480
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8361
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8353
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8343
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8342
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8323
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.8313
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8295
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8173
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8147
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8119
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8118
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8070
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8031
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8011
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7927
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7918
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7912
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7903
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7867
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7725
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7723
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7720
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7706
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7687
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7681
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7676
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7665
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7626
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7624
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7620
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7596
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7537
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7512
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7489
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7489
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7469
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7447
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7423
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7418
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7390
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	6	0.7378
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7371
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7358
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7354
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7342
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7321
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7309
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7286
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7283
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7277
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7267
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7261
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7254
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7253
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7251
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7224
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7223
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7221
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7206
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7200
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7182
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7177
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7149
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7131
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7120
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7115
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7112
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7108
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7104
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7089
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7083
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7080
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7076
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7071
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7067
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7065
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7047
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7046
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7046
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7026
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7025
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7024
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7021
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	3	0.7020
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7018
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7018
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7007
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7004
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7003

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