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Apigenin 7-O-(glucosyl-(1→2)-glucosyl-(1→6)-glucosyl-(1→2)-glucoside

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

Canonical Smiles	OCC1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(cc2)O)C([C@H]([C@@H]1O)O)O[C@@H]1OC(CO[C@@H]2OC(CO)[C@@H]([C@@H](C2O[C@@H]2OC(CO)[C@H]([C@@H](C2O)O)O)O)O)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C39H50O25/c40-8-19-24(46)28(50)32(54)36(59-19)63-34-30(52)25(47)20(9-41)60-38(34)56-11-22-27(49)29(51)33(55)37(62-22)64-35-31(53)26(48)21(10-42)61-39(35)57-14-5-15(44)23-16(45)7-17(58-18(23)6-14)12-1-3-13(43)4-2-12/h1-7,19-22,24-44,46-55H,8-11H2/t19?,20?,21?,22?,24-,25+,26-,27-,28+,29?,30+,31+,32?,33+,34?,35?,36+,37+,38-,39-/m1/s1
InChIKey	XWRGAQKULUSJDR-DMAPHTNASA-N
Formula	C₃₉H₅₀O₂₅
HBA	25
HBD	15
MW	918.8
Rotatable Bonds	13
TPSA	407.5
LogP	-6.48
Number Rings	7
Number Aromatic Rings	3
Heavy Atom Count	64
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	918.26
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hyacinthoides lingulata	Asparagaceae	Plantae	81761

Showing of synonyms

Hanfer M, Benramdane Z, et al. (2022). Chemical constituents, in vitro anti-inflammatory, antioxidant and hemostatic activities of the n butanol extract of Hyacinthoides lingulata (Poir.) Rothm. Natural product research, 2022, 36(12), 3124-3128. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1OC2C(OCCC2)OCC3CCCC(O3)OC4C(OCCC4)Oc(cc5)cc(c56)oc(cc6=O)-c7ccccc7

Level: 5

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OCC3CCCC(O3)OC4C(OCCC4)Oc(cc5)cc(c56)occc6=O

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3C(OCCC3)Oc(cc4)cc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3C(OCCC3)Oc(cc4)cc(c45)occc5=O

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)OCC3CCCC(O3)OC4CCCOC4

Level: 3

Mol. Weight: 918.8 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1COC(OCCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 918.8 g/mol

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 918.8 g/mol

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

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 918.8 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 918.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 918.8 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 918.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.6
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1815.1
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 238141.25

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.66
Plasma Protein Binding: 15.09
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: 4.43
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -5527.79
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.53
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.06
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: -432207060.47
Rat (Acute): 2.85
Rat (Chronic Oral): 5.26
Fathead Minnow: 545578.78
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: 48604023.91
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -15.61
Log(P): -2.71
Log S: -3.37
Log(Vapor Pressure): -1600394.5
Melting Point: 216.56
pKa Acid: -11592.69
pKa Basic: -66.09

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9502
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9501
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9218
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9128
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.8890
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8830
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8791
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8785
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8778
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8757
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8704
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8651
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8619
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8593
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8581
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8569
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8363
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8344
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8303
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8184
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8112
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8092
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8082
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8062
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8042
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7986
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7970
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7948
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7911
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7884
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7862
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7836
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7812
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7803
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7776
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7776
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7762
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7738
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7662
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7660
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7648
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7608
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7589
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7583
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7573
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7558
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7502
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7500
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7448
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7417
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7403
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7342
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7322
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7299
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7293
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7243
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7234
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7211
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7209
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7196
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7190
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7187
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7180
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7155
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7150
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7149
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7133
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7129
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7107
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7103
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7102
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7101
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7095
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7086
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7071
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7070
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	3	0.7046
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7039
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7036
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7032
DNA mismatch repair protein MutS	P23909	MUTS_ECOLI	Escherichia coli	3	0.7027
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7025
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7014
Genome polyprotein	P12823	POLG_DEN2P	Dengue virus type 2	3	0.7013
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7013

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