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Kaempferol-3-O-(2,6-di-E-p-coumaroyl)-glucoside

Family: Plantae - Umbelliferae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	O=C(OC[C@H]1OC(Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C\c1ccc(cc1)O)/C=C\c1ccc(cc1)O
InChI	InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)35(49)38(53-31(46)16-6-21-3-11-24(41)12-4-21)39(52-29)54-37-34(48)32-27(44)17-26(43)18-28(32)51-36(37)22-7-13-25(42)14-8-22/h1-18,29,33,35,38-44,47,49H,19H2/b15-5-,16-6-/t29-,33-,35+,38-,39?/m1/s1
InChIKey	YXXQUJGFZPLXJV-AAYKWORQSA-N
Formula	C₃₉H₃₂O₁₅
HBA	15
HBD	7
MW	740.67
Rotatable Bonds	10
TPSA	242.88
LogP	3.7
Number Rings	6
Number Aromatic Rings	5
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	740.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eryngium triquetrum	Umbelliferae	Plantae	1094608

Showing of synonyms

Bouzergoune F, Ciavatta M.L, et al. (2016). Phytochemical Study of Eryngium triquetrum: Isolation of Polyacetylenes and Lignans. Planta Med,2016,82(16),1438-1445. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCC(C(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5)OC(=O)C=Cc6ccccc6

Level: 4

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCC(C(O2)Oc(c3=O)coc(c34)cccc4)OC(=O)C=Cc5ccccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCC(CO2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 740.67 g/mol

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

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.67 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 11.46
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2235.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.03
Plasma Protein Binding: 76.98
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 9.63
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -53.39
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.27
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.76
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -4056839.23
Rat (Acute): 2.39
Rat (Chronic Oral): 3.94
Fathead Minnow: 5128.8
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 448710.17
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.17
Log(P): 5.41
Log S: -6.81
Log(Vapor Pressure): -14776.92
Melting Point: 249.21
pKa Acid: -73.52
pKa Basic: 3.63

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9710
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9372
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.9365
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.9350
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9215
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.9029
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.9029
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8997
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8953
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8949
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8911
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8827
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8826
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8694
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8692
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8687
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8676
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8626
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8558
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8558
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8468
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8467
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8432
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8430
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8414
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8338
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8259
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8233
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.8229
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8224
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8183
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.8170
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8091
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8078
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8068
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8050
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8007
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7988
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7941
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7921
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7894
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7857
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7833
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7828
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7799
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7797
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7796
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7787
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7766
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7750
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7746
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7730
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7721
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7695
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7665
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7662
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7625
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7625
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7610
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7605
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7603
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7592
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7589
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7567
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7556
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7536
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7519
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7517
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7502
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.7496
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7495
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7494
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.7487
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7478
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7478
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7442
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7436
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7415
Mitogen-activated protein kinase kinase kinase 7	O43318	M3K7_HUMAN	Homo sapiens	3	0.7377
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7360
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7340
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7318
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7314
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7297
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7295
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7286
L-lactate dehydrogenase	Q5SJA1	LDH_THET8	Thermus thermophilus	3	0.7282
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7269
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7259
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7253
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7243
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7221
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7221
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7220
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7218
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7216
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7199
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7186
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7183
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7163
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7145
Pol protein	Q000H7	Q000H7_9HIV1	Human immunodeficiency virus 1	3	0.7128
Seed lectin subunit I	P05045	LEC1_VIGUC	Vigna unguiculata subsp. cylindrica	3	0.7118
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7117
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7114
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7099
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7096
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7093
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7086
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7083
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7077
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7064
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7063
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7058
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7056
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	4	0.7054
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7043
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7038
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7035
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7012
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7012
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7006
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	2	0.7005
Aminopeptidase N	P04825	AMPN_ECOLI	Escherichia coli	3	0.7003
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7002

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