ANPDB

Select a section from the left sidebar

Kaempferol3-O-(2 ́ ́-O-E-p-coumaroyl)-beta-D-glucopyranoside

Family: Plantae - Fagaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	O=C(OC[C@H]1O[C@@H](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-AIBWQOBZSA-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	Rubus rigidus	Rosaceae	Plantae	59497
2	Quercus ilex	Fagaceae	Plantae	58334

Showing of synonyms

Nguelefack TB, Mbakam FH, et al. (2011). A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.. Archives of pharmacal research,2011, 34(4), 543-550. [View] [PubMed]
Hadidi L, Babou L, et al. (2017). Quercus ilex L.: How season, plant organ and extraction procedure can influence chemistry and bioactivities. Chemistry & Biodiversity, 2017, 14(1),. [View] [PubMed]

Pubchem: 10439991

Cas: 121651-61-4

Zinc: ZINC000095912577

Nmrshiftdb2: 70048545

Chembl: CHEMBL3628129

Bindingdb: 50129556

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): -6.68
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: 81.22
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: 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: 9.62
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -53.42
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: 7.75
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: -4056836.4
Rat (Acute): 2.39
Rat (Chronic Oral): 3.94
Fathead Minnow: 5128.62
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 448712.65
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.21
Log(P): 5.48
Log S: -6.85
Log(Vapor Pressure): -14780.12
Melting Point: 268.64
pKa Acid: -73.36
pKa Basic: 3.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9766
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9412
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9410
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9163
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9025
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.9004
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8961
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8861
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8821
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8801
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8652
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8647
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8643
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8610
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8583
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8508
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8498
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8426
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8399
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8356
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8292
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8230
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8216
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8216
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8201
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	4	0.8163
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8147
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8063
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7976
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7960
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7942
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7916
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7913
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7883
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7850
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7826
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7803
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7787
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7783
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7731
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7716
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7628
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7607
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7596
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7565
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7549
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7512
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7500
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7496
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7427
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7385
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7382
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7378
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7326
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7297
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7260
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7254
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7250
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7247
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7243
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7224
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7224
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	4	0.7222
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7186
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7181
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7173
Genome polyprotein	C0LMU0	C0LMU0_9FLAV	dengue virus type 3	3	0.7157
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7149
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7148
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7126
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7122
Chromosome partitioning protein ParA	B0ZE06	B0ZE06_ECOLX	Escherichia coli	3	0.7121
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7118
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7118
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7109
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7107
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7101
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7100
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7095
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7091
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7063
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	4	0.7060
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7055
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7055
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7051
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7048
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7038
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7034
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	4	0.7023
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7009
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7007
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7004
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7004

Download SDF