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Genkwanin 8-C-beta-glucopyranoside

Family: Arecaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	OCC1O[C@@H]([C@H](C([C@@H]1O)O)O)c1c(OC)cc(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI	InChI=1S/C22H22O10/c1-30-14-7-12(26)16-11(25)6-13(9-2-4-10(24)5-3-9)31-21(16)17(14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-24,26-29H,8H2,1H3/t15?,18-,19?,20+,22-/m1/s1
InChIKey	HHPLIFSIFJSIBY-OBSFFFLGSA-N
Formula	C₂₂H₂₂O₁₀
HBA	10
HBD	6
MW	446.41
Rotatable Bonds	4
TPSA	170.05
LogP	0.39
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	446.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Livistona australis	Arecaceae	Plantae	115491

Showing of synonyms

Kassem MES, Shoela S, et al. (2012). A sulphated flavone glycoside from Livistona australis and its antioxidant and cytotoxic activity. Natural Product Research,2012,26(15),1381-1387. [View] [PubMed]

Pubchem: 163013085

Nmrshiftdb2: 70093069

No compound-protein relationship available.

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 306.36 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 230.26 g/mol

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

Level: 1

Mol. Weight: 222.24 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 146.14 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.57
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.27
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.96
Plasma Protein Binding: 76.59
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: 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: 11.68
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.84
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.99
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.68
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: -79.39
Rat (Acute): 2.44
Rat (Chronic Oral): 3.95
Fathead Minnow: 4.05
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 591.24
Hydration Free Energy: -4.57
Log(D) at pH=7.4: 1.2
Log(P): 1.04
Log S: -4.69
Log(Vapor Pressure): -11.55
Melting Point: 204.67
pKa Acid: 5.77
pKa Basic: 6.11

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9336
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9336
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9271
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9271
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.9021
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.9021
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8954
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8954
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8689
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8689
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8605
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8605
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8575
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8575
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8456
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8456
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8449
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8449
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8248
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8248
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8148
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8148
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8137
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8137
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8094
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8094
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8092
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8092
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7968
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7968
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7939
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7939
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7920
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7920
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7857
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7857
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7789
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7789
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7772
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7772
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7770
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7770
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7613
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7613
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7609
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7609
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7580
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7580
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7559
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7559
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7548
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7548
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7509
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7509
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7502
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7502
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7413
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7413
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7392
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7392
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7383
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7383
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7366
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7366
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7321
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7321
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7261
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7261
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7218
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7218
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7212
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7212
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7169
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7169
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7167
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7167
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7120
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7120
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7095
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7095
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7094
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7094
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7091
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7091
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7086
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7086
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7059
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7059
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7040
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7040
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7038
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7038
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7015
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7015
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7005
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7005

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